Beautifully renovated and exceptionally well-appointed, this 5,139-square-foot lakefront residence combines space, privacy and indoor-outdoor living on Lake Sawyer in Windermere. A private gated entrance introduces the two-story Mediterranean home, extensively renovated in 2019 with a sophisticated interior and functional floor plan designed for everyday living and entertaining. From the foyer, views extend through the formal living room to the screened pool and lake beyond. The main level is thoughtfully arranged with the primary suite privately positioned on one side and the kitchen, family room and casual living spaces on the other. The renovated kitchen features extensive white cabinetry extending to the ceiling, quartz surfaces and backsplash, and an oversized contrasting island with seating for four, abundant storage and an undermount sink. A professional-style gas range with pot filler and custom vent hood is complemented by double wall ovens, warming drawer, stainless refrigerator and dishwasher. Glass-front cabinetry, under-cabinet lighting and statement lighting add detail. The kitchen opens to the breakfast area and family room with views toward the pool and lake and is adjacent to the formal dining room, connected by a wet bar. A separate built-in beverage station with undercounter refrigeration and a wine closet further enhance the home's entertaining spaces. Privately positioned on the first floor, the primary suite features a detailed tray ceiling, layered crown molding, custom interior shutters and direct access to the covered outdoor living area with lake views. An expansive custom dressing closet offers floor-to-ceiling cabinetry, extensive hanging space, drawers, shoe storage and display shelving. The renovated primary bath includes a long dual-sink vanity, freestanding soaking tub and oversized open shower with dual entrances, herringbone-patterned tile and stacked-stone feature wall. Upstairs, four additional bedrooms are joined by living space, a dedicated theater and flexible bonus room, providing versatility for family, guests, work and recreation. The rear of the home is designed around the lake, with large expanses of glass connecting the interior to the screened pool and spa, expansive deck and substantial covered lanai. An upper-level covered balcony provides another vantage point overlooking the pool and water. The pool, surface, tile and deck underwent a major renovation around 2017. Beyond the pool, about 80 feet of Lake Sawyer frontage leads to a private dock and boathouse with covered boat lift and two Jet Ski lifts. Lake Sawyer connects with Little Lake Sawyer, offering the opportunity to boat, swim and enjoy life on the water directly from home, with sunset views and distant Disney fireworks adding to the magic. Additional features include a three-car attached garage, whole-house generator, climate-controlled storage, tankless water heater, private well with water-treatment system, insulated interior walls and updated LED lighting. Despite its private lakefront setting, the home is convenient to shopping, dining, golf, recreation, major roadways and area attractions and is especially convenient to Windermere Preparatory School. Zoned for Windermere Elementary, Bridgewater Middle and Windermere High School, this is an exceptional opportunity to enjoy beautifully renovated interiors, generous entertaining spaces, a private pool and true lakefront living in the heart of Windermere.

12722 S Lake Sawyer Lane, Windermere

Listing courtesy of KELLY PRICE & COMPANY LLC. 407-645-4321

$1,250,000

O6446547 MLS

Build Your Dream Lakefront Home in the Town of Windermere! Opportunity is knocking in one of Central Florida’s most desirable areas! This exceptional one-acre lakefront homesite on Oakdale Street in the town offers a rare opportunity to bring your vision to life and build the custom home you have always dreamed of. With an impressive 105 feet of direct frontage on beautiful Lake Bessie, this property provides the space, privacy, and waterfront setting to create something truly special. One of the biggest advantages of this property is NO HOA. Enjoy the freedom and flexibility that comes with owning your own piece of land without the restrictions and monthly fees often associated with planned communities. Whether you envision a stunning custom estate, a spacious family home, or a private lakeside retreat, this property gives you the opportunity to create a home that is uniquely yours. The expansive one-acre lot provides plenty of room to design the lifestyle you want. Imagine a beautiful custom residence with expansive living spaces, a resort-style pool, outdoor entertaining areas, lush landscaping, a private garden, oversized garage, and breathtaking views of Lake Bessie. With 105 feet of lake frontage, you can take full advantage of the waterfront setting and enjoy the beauty and tranquility of lakefront living right in the heart of Windermere. Instead of settling for someone else’s floor plan, start with a blank canvas and create a home designed around the way you live. Bring your architect, builder, and ideas and transform this exceptional homesite into your own private sanctuary. Location is everything, and this property offers the best of the Old Windermere lifestyle. Ideally located within a short distance of the Windermere Farmers Market, local shops, restaurants, and more, while beautiful Lake Butler is just blocks away. Town residents also have access to a boat ramp on Lake Butler and Lake Bessie, along with tennis courts, providing even more opportunities to enjoy the outdoors and the unique lifestyle that makes Windermere so desirable. Windermere is known for its beautiful lakes, charming community atmosphere, desirable residential neighborhoods, and convenient proximity to everything that makes Central Florida such a sought-after place to live. Opportunities to own a large lakefront homesite with no HOA and 105 feet of Lake Bessie frontage are truly special. This is your opportunity to stop dreaming about the perfect home and start building it. Make your vision come to life. Make this exceptional Windermere lakefront property the place you call home. Don't miss this rare opportunity!

1221 Oakdale Street, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396

5092 Isleworth Country Club Drive, Windermere

$8,500,000

4 Beds ⋅ 5 Baths ⋅ O6446272 MLS

Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.

5092 Isleworth Country Club Drive, Windermere

Listing courtesy of ISLEWORTH REALTY LLC. 407-909-9000

$950,000

4 Beds ⋅ 3 Baths ⋅ G5118124 MLS

Virtually Staged. This home can be purchased with NO INCOME VERIFICATION needed! Seller's preferred lender is willing to contribute 1% of the loan amount toward the buyer's interest rate buy-down. Welcome to 8524 Vivaro Isle Way, a beautifully appointed home in the sought-after Windermere Isle community. Designed for both everyday comfort and entertaining, this home features a private custom pool, upgraded 42" kitchen cabinetry with crown molding, granite countertops, upgraded cabinet hardware, a single-basin undermount sink, and a stylish kitchen backsplash. Upgraded tile flooring extends through the foyer, dining room, family room, office, gallery, kitchen/breakfast area, laundry room, and bathrooms, while the remaining living areas feature carpet. The primary suite offers a raised-height vanity, upgraded undermount sink, semi-frameless shower enclosure, tiled shower, and ceiling-mounted rain shower. Additional upgrades include 8' interior doors, blinds throughout operable windows, a 9' sliding glass door, upgraded bathroom vanities, and upgraded interior finishes. All rooms are upgraded with ceiling fans and light fixtures. Step outside to enjoy your own private pool and create the ideal Florida lifestyle with plenty of space to relax, entertain, and enjoy the sunshine. Located in Windermere Isle, this home offers convenient access to shopping, dining, parks, and recreation, with Winter Garden Village, Lakeside Village, Hamlin, and Walt Disney World-area attractions all within the surrounding area. With its combination of thoughtful upgrades, private outdoor living, and a convenient location near the Windermere and Winter Garden areas, this home offers an ideal place to enjoy Central Florida living.

8524 Vivaro Isle Way, Windermere

Listing courtesy of SERHANT. helloflorida@serhant.com

$875,000

4 Beds ⋅ 3 Baths ⋅ O6445423 MLS

This beautifully maintained 4 Bedroom, 3-Bath Pool home is located in a desirable 24-hour guard-gated Windermere community. Offering a spacious and versatile floor plan, this home features 3 bedrooms on the main level, a dedicated flex/office space, formal living and dining rooms, and an inviting family room ideal for everyday living and entertaining. Upstairs, the private 4th Bedroom provides wonderful flexibility and can easily serve as a guest suite, bonus room, media room, or additional home office. Outside, enjoy the Florida lifestyle from the expansive screened in patio and sparkling salt water pool with a beautiful conservation view! A gas line is already piped to the exterior, providing the opporunity to create a future summer kitchen. Additional highlights include a 3 Car Garage, 2022 Tile Roof, Fresh Exterior Paint, Irrigation System, Security System, and an Orkin Termite Bond for added peace of mind. Ideally located in Windermere with convenient access to major shopping, dining, entertainment, and area amenities, this home combines space, flexibilty, privacy, and a resort-style outdoor living in one exceptional property.

11727 Delwick Drive, Windermere

Listing courtesy of BHHS FLORIDA REALTY. 407-876-2090

$3,850,000

4 Beds ⋅ 6 Baths ⋅ O6446042 MLS

Welcome to an exceptional estate built in 2016 by Wyatt, nestled within the prestigious guarded gates of Isleworth. Ideally situated in the intimate Gardens of Isleworth, this beautifully appointed two-story residence offers approximately 6,600 square feet of refined living space, complemented by serene water views, lush landscaping, and a private walking trail. Elegant interiors showcase inlaid wood and travertine flooring, custom ceiling details, a beautiful fireplace, and expansive sliding glass pocket doors that effortlessly connect the interior living spaces to the spectacular outdoor retreat. The chef’s kitchen is designed for both everyday living and sophisticated entertaining, featuring Viking appliances, a striking copper hood, oversized center island, wet bar, butler’s pantry, breakfast nook, and hidden walk-in pantry. The luxurious primary suite offers a private lounge, dual-sided fireplace, cozy sitting area, dual walk-in closets, dressing area, and spa-inspired bath with dual vanities, soaking tub, and an impressive indoor-outdoor shower. Additional highlights include a private theater, balcony, bonus space, elevator, whole-house generator, and a smart-home system. Outdoor living is exceptional, featuring a sparkling pool and spa, fire pit, summer kitchen, outdoor shower, and expansive covered lanai with retractable screens, creating a comfortable year-round setting for relaxing and entertaining while overlooking the tranquil water. An extraordinary six-car garage setup includes four individual single-car garages, with two equipped with vehicle lifts. This exceptional residence seamlessly combines sophisticated design, modern technology, resort-style outdoor living, and privacy within one of Windermere’s most coveted guard-gated communities. Grounds maintenance is included through the HOA. Be sure to explore the virtual tour links for an immersive look at this remarkable Isleworth estate.

4906 Aviva Garden Court, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396

$6,950,000

7 Beds ⋅ 8 Baths ⋅ O6443311 MLS

Set behind the guarded gates of Keene's Pointe, lies this masterfully crafted 7-bedroom, 8-bath lakefront estate by Stonebridge Custom Homes presenting an extraordinary opportunity for those seeking uncompromising elegance and everyday indulgence. Expertly designed to invite abundant natural light throughout its over 8700 sqft magnificent interiors while still offering complete privacy and astounding wooded and lake views over its 4+ acre grounds. A stately brick-paver drive, twin motor courts with garage parking for 4 cars and a golf cart, set the tone for the refined lifestyle that awaits within. Through 10-foot solid double doors, the foyer opens to a two-story travertine-tiled formal living area with dramatic stone fireplace and towering windows that frame views of the pool and lake. The kitchen is a culinary masterpiece, featuring a hidden walk-in pantry, Thermador commercial grade appliance suite, including full-size refrigerator and separate freezer, Bosch Dishwasher, Scotsman Ice maker, Busby cabinets, granite countertops, and a double island setup designed for effortless entertaining. A beverage bar connects the kitchen to the formal dining room and iron-gated wine room with 45 bottle Brisa wine refrigerator. The open-concept layout offers casual dining off the kitchen and a family room that flows seamlessly into theatre-style lounge. The first-floor primary suite is a study in calm sophistication, featuring sitting area, poolside terrace access, coffee bar, 2 custom walk-in closets, and a spa-inspired ensuite with dual granite topped vanities, soaking tub, and multi-head steam shower. An executive study, bonus storage, mudroom and laundry, 2 powder rooms, and a private ensuite for visiting guests, complete the first floor. Upstairs, a bonus room for exercise or crafting, an open area for study or reading, add’l laundry, and 5 spacious bedrooms complemented by 4 full baths, ensure every guest enjoys comfort and privacy. From hidden storage and bonus rooms to thoughtfully curated finishes, every detail has been considered with intention and care. Impeccably maintained and thoughtfully updated where it matters, delivering peace of mind as well as prestige (See feature sheet for a full list of updates). Five sets of wall-to-wall sliders open the beautifully appointed interiors to the private outdoor retreat where guests will want to linger. A summer kitchen and outdoor bar overlook the pool with rock waterfall and spa, while an outdoor gas fireplace anchors evenings that stretch long past sunset. The covered lanai areas are enhanced by electronically controlled invisible screens and a mosquito misting system. The beautifully landscaped grounds and fenced backyard extend to a private dock with covered boathouse and electronic lift, providing effortless access to the pristine waters of Lake Tibet and the interconnected Butler Chain of Lakes. Residents of Keene’s Pointe enjoy a country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, pickleball, dining, and a vibrant social calendar. Positioned minutes (3.5 mi.) from historic Windermere with easy access to Orlando's attractions. Furnishings and Regal LS4 Power Boat are negotiable for a truly turnkey move.

6113 Grosvenor Shore Drive, Windermere

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211

$565,000

3 Beds ⋅ 2 Baths ⋅ O6445539 MLS

7271 Londale Blvd is a one-story Windermere home with an open layout and a large kitchen island. The kitchen has white cabinetry, stainless steel appliances, and counter space, and it opens to the dining and living areas. Bedrooms have neutral finishes, and the bathrooms have tile surrounds and vanities. A screened patio overlooks the lawn, with mature landscaping around the house. An attached one-car garage and a broad driveway sit at the front. Included 100-Day Home Warranty with buyer activation

7271 Londale Boulevard, Windermere

Listing courtesy of OPENDOOR BROKERAGE LLC. Homes@opendoor.com

9310 Isleworth Gardens Drive, Windermere

$3,595,000

3 Beds ⋅ 5 Baths ⋅ O6442366 MLS

Set within the Gardens of Isleworth, an intimate enclave of custom homes surrounded by lush gardens, water features, bridges and walking paths, this elegant single-story garden villa offers elevated garden views. The residence pairs timeless Mediterranean architecture with sophisticated finishes and a seamless indoor-outdoor design. Beautiful finishes throughout the interior include travertine flooring, wood-beamed ceilings and solid wood doors, creating a warm and gracious aesthetic. The expansive kitchen is designed for both everyday living and entertaining, with double islands, Quartzite countertops, a marble mosaic backsplash, Wolf appliances, a gas range, wet bar and butler’s pantry. A stone fireplace provides a focal point in the living room, while the spacious family room opens through panoramic sliding doors to a covered lanai, extending the living spaces naturally outdoors.The primary suite offers a private retreat with a morning bar, sitting area, spa-inspired bath and generous walk-in closet. A wood-floored study with custom built-ins provides an elegant setting for work, while additional bedrooms offer comfort and privacy for family and guests. Additional interior highlights include the laundry room, powder bath, and a three-car garage.Beyond the interiors, the home embraces its lush garden setting with tranquil pond views and an expansive outdoor living area. The covered lanai features a summer kitchen and pool bath overlooking a heated saltwater pool and spa, creating a private setting for relaxed afternoons and beautiful entertaining. The Gardens of Isleworth offer convenient living in a beautiful setting within Central Florida’s most iconic golf course community.

9310 Isleworth Gardens Drive, Windermere

Listing courtesy of ISLEWORTH REALTY LLC. 407-909-9000

$3,999,000

5 Beds ⋅ 6 Baths ⋅ O6445244 MLS

Keene’s Pointe – 24-hour gated/attended community in Windermere, Florida. Experience refined luxury in this exceptional golf-front estate perfectly positioned along the 17th fairway of The Golden Bear Club. Fully renovated, architecturally refined and intentionally designed by Ashley Martin Home. From the moment you enter, an inviting foyer opens to a spacious living room framed by 12-foot ceilings, expansive windows, and views of the course, filling the home with natural light and warmth, as well as a functional dining room with built-in cabinetry, perfect for entertaining. Designed with both elegance and functionality in mind, the home features wide-plank hardwood flooring throughout, custom drapery and shades, and extensive upgraded lighting and finishes. The private office is a standout, complete with rich built-in cabinetry and a wood-accent ceiling that creates a sophisticated workspace. The primary suite is a true retreat, accessed through a private vestibule-style entrance offering a serene escape. Inside, enjoy access to the outdoors, a spa-inspired bath with a freestanding tub, an oversized walk-in shower, and a spacious custom walk-in closet with built-ins. The chef’s kitchen is thoughtfully appointed with built-in refrigeration and dishwasher, an appliance garage, a large center island, Butler’s pantry with wine refrigeration, and a generous breakfast nook. A mud area with built-ins adds everyday convenience, while the family room showcases custom built-ins for effortless living. The home offers a versatile and spacious layout, including two ensuite bedrooms with walk-in closets on the main level, and two additional bedrooms upstairs connected by a shared bath. The second floor also features a loft with built-ins that can easily function as a fifth bedroom, playroom or media room, along with a bonus space overlooking the golf course—currently used as a gym, but ideal for a game room or lounge. Outdoor living is equally impressive, featuring a saltwater pool and spa, fire pit, cabana with summer kitchen, and a private putting green. The fenced yard and retractable screened lanai create a seamless indoor-outdoor experience, while a convenient exterior-access half bath serves the pool area. Additional highlights include a well-appointed laundry room with stacked washer and dryer, and a four-car garage with high ceilings and custom flooring, and much more! This turn-key home can be purchased fully furnished and decorated. Conveniently located to shopping, dining, expressways, tourist attractions, and top-rated public and private schools, this is a rare opportunity to own a meticulously designed, luxury estate that blends comfort, style, location, and stunning golf course views into one extraordinary residence.

6120 Greatwater Drive, Windermere

Listing courtesy of SOUTHERN REALTY GROUP LLC. 407-217-6480

$2,350,000

4 Beds ⋅ 6 Baths ⋅ O6444548 MLS

SINGLE STORY LIVING and PRIVATE PEDESTRIAN-GATED ACCESS to WINDERMERE PREPARATORY SCHOOL from within the community distinguish this custom Waterstone home. Built in 2014 and located behind a staffed, guard-gated entrance, the residence offers approximately 4,169 square feet, four bedrooms, four full baths, two half baths, and a three-car garage. Two stately palms welcome you to the beautifully landscaped 0.44-acre homesite, while landscape lighting highlights the grounds after sunset. From the moment you enter, the view opens to the CENTRAL COURTYARD, SALTWATER POOL, and SPA. Direct access from the kitchen, family room, and primary suite makes the courtyard part of daily life. Covered lanais, generous lounging areas, a summer kitchen with a full-size motorized screen, and an outdoor fireplace provide space to gather and dine outdoors. The courtyard has been freshly painted, and the travertine pavers were recently sealed. Inside, soaring ceilings, tray details, crown molding, and expansive windows bring light and courtyard views into the living spaces. The kitchen features Wolf and Sub-Zero appliances, rich wood cabinetry, dual islands, bar seating, and a concealed walk-in pantry. The spacious primary suite includes hardwood flooring, a sitting area, two expansive custom walk-in closets, and a bath with a soaking tub, oversized rainfall shower, and generous vanity space. An adjoining flex room can serve as a home office, gym, or private retreat. Additional features include two newer air-conditioning units serving the multizone HVAC system, a sound system throughout the indoor and outdoor living areas, a whole-house Lorex camera system, a porte-cochère, and an expansive paver driveway. Waterstone is near Windermere High School, with convenient access to Winter Garden Village, Lakeside Village, Walt Disney World, and major Orlando routes. Schedule a private showing to experience this distinctive Windermere courtyard home.

11532 Waterstone Loop Drive, Windermere

Listing courtesy of BHHS FLORIDA REALTY. 407-876-2090

$1,295,000

6 Beds ⋅ 5 Baths ⋅ O6443475 MLS

No detail overlooked in this beautifully reimagined 6BR/5BA estate in the sought-after lakefront community of Windermere Downs! Fully renovated and expanded with high-caliber craftsmanship, this home offers the ultimate Central Florida lifestyle. The lower level boasts rich tongue-and-groove ceilings, hardwood floors, plantation shutters, double-pane vinyl windows, and bright natural light. The expansive primary suite features a custom 10’x20’ walk-in closet and spa-like bathroom. Every bedroom enjoys en-suite bath access, including the private 780 sq ft upper-level suite with stunning Lake Down sunset views. The spacious kitchen and breakfast nook anchor the home, flowing into a living room with a stunning floor-to-ceiling picture window and French doors that open to your backyard oasis. Step outside to a private resort-style paradise complete with a sport pool, sun shelf, earth-toned pavers, summer kitchen, fire pit, and remodeled pool bath. Major mechanical updates ensure total peace of mind: Spray foam insulation (2025), main HVAC (2019-2023), new water heater, upgraded plumbing, lighting, and interior laundry room. Enjoy deeded access to the Butler Chain of Lakes via Windermere Downs’ crown jewel private beach lot on Lake Down, plus tennis/pickleball courts and park spaces. Unbeatable location—10 mins to Turnpike/408/429 and 25 mins to Disney, MCO Airport, and Downtown Orlando!

9668 Woodmont Place, Windermere

Listing courtesy of DIAMOND REAL ESTATE GROUP. 407-279-0448

$1,488,000

4 Beds ⋅ 4 Baths ⋅ O6440411 MLS

Welcome to 12721 Jacob Grace Court, an exceptional residence nestled within the highly sought-after gated enclave of Tildens Grove in Windermere. Ideally positioned on a quiet cul-de-sac, this remarkable property sits on over a half-acre homesite with serene conservation and pond views, offering a rare combination of privacy, space, and natural beauty. From the moment you enter, you are greeted by an inviting floor plan filled with abundant natural light and elegant finishes throughout. Just past the two-story foyer, executive home office and formal living room, the expansive main living areas are thoughtfully designed to flow seamlessly, creating the perfect setting for both everyday living and sophisticated entertaining. The heart of the home is the beautifully renovated kitchen, featuring generous cabinetry, quality appliances, and ample counter space, all overlooking the main living and dining areas with stunning private views. The primary suite serves as a tranquil retreat, complete with a spa-inspired bath and spacious walk-in closet. Additional second floor bedrooms provide balcony access and flexibility for family, while a first-floor bedroom and bonus room offer an ideal layout for a private guest sanctuary. Step outside and discover one of the home’s most captivating features—a sprawling backyard with a two-story screen enclosure that is anchored by a resort-style pool, spa and expansive entertaining areas set against conservation and water views. Residents of Tildens Grove enjoy a premier lifestyle with gated access, tree-lined streets, tennis courts, playground and proximity to top-rated schools, boutique shopping, dining, golf, and all the attractions that make Windermere one of Central Florida’s most desirable locations.

12721 Jacob Grace Court, Windermere

Listing courtesy of LAKE NONA REALTY LLC. 407-851-9091

11446 Jasper Kay Terrace Unit 202, Windermere

$295,000

2 Beds ⋅ 2 Baths ⋅ O6442239 MLS ⋅ 14466 BLDG.

Welcome to easy Florida living in the desirable Lakeside community of Windermere! This beautifully maintained 2-bedroom, 2-bathroom condo offers a comfortable open-concept layout with plenty of natural light and a warm, inviting feel throughout. The spacious living and dining areas create an ideal setting for both everyday living and entertaining, while the well-appointed kitchen offers modern appliances, generous counter space, and plenty of room. The primary suite features a private en-suite bath and ample closet space, while the second bedroom offers flexibility for guests, a home office, or additional living needs. Step outside to your private balcony and enjoy your morning coffee or unwind at the end of the day while taking in the peaceful community surroundings. Residents of Lakeside enjoy a variety of amenities designed for an active and relaxed lifestyle, including a community pool, fitness center, and walking trails. Conveniently located near shopping, dining, entertainment, and highly sought-after Windermere-area schools, this home offers the perfect combination of comfort, convenience, and community. Whether you're looking for a low-maintenance primary residence, a place to settle into the Windermere lifestyle, or a smart addition to your real estate portfolio, this condo is ready to welcome you home.

11446 Jasper Kay Terrace Unit 202, Windermere

Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS. 407-629-4420

14350 Bridgewater Crossings Boulevard, Windermere

$405,000

4 Beds ⋅ 3 Baths ⋅ O6444644 MLS ⋅ 14350 BLDG.

Come be wow'd by this 4/2.5 bedroom water view townhome that faces Bluebird Pond and garden area from front porch with primary bedroom on main level. Primary bedroom has views of and access to an additional private back porch. Primary bath offers stand alone shower, generous walk in closet and granite counters. Three secondary bedrooms upstairs with views of Bluebird Pond also have access to separate loft space as additional living room, playroom, game room, study, den or library. Any chef would enjoy cooking in this kitchen with views of and access to private back porch, generous granite counter space, large pantry, stainless steel appliances with new microwave and tall cabinets. Half bath downstairs has been remodeled and is just off the living room and kitchen area. Laminate wood floors throughout downstairs and crown molding in the living and dining areas. Entire interior, including ceilings, has been freshly painted. Brand new carpet in upstairs rooms. Roof is 2022, A/C is 2026, Hot water heater is 2026 as well. Two car garage with covered access to home and amble driveway space plus additional guest parking in front of home. From the photos you will see you are walking distance (less than .3 miles) to Foxtail Coffee, Marcos Pizza, Kelly's Ice Cream, the dog park, children's playground, and Keene's Crossing Elementary School. The community offers (also within walking distance) community pool, tennis and pickleball courts, fitness centers, clubhouse, and many miles of walking trails. You simply can't beat this location, zoned A rated schools, and 15 min to Disney theme parks, easy access to major thoroughfares, international airport, fine dining, entertainment, etc.

14350 Bridgewater Crossings Boulevard, Windermere

Listing courtesy of BLUE MAGNOLIA REALTY LLC. 407-415-3365

$560,000

4 Beds ⋅ 3 Baths ⋅ S5158277 MLS

WINDERMERE OPPORTUNITY! Welcome to this beautiful 4-bedroom, 2.5-bath home offering 2,214 sq. ft. in the desirable Westside Village community. Built in 2018, this home offers a spacious open-concept layout designed for both everyday living and entertaining. The first floor features luxury vinyl flooring, while the upgraded kitchen offers marble countertops, generous workspace and an open flow into the main living areas. A versatile bonus/flex space provides additional room for a media area, game room, home office or additional living space. Enjoy the benefits of solar panels, offering added energy-efficiency potential. Includes custom drapes on all windows. IMPORTANT: Solar panels are subject to an existing financing obligation that must be assumed by the Buyer, subject to approval by the solar financing/provider company. Buyer to independently verify remaining balance, monthly payment, transfer requirements and all solar terms. Westside Village offers resort-style community amenities including a pool, clubhouse, playground and walking trails. Ideally located near shopping, dining, major roadways and the Disney area. Previous marketing of the property has also highlighted views of the Disney fireworks from the home. Buyer may qualify for up to $3,000 in lender credits toward closing costs when financing with Seller’s preferred lender. Schedule your private showing today and discover the space, location and lifestyle this Windermere home!

11543 Charnock Drive, Windermere

Listing courtesy of PM ELITE REALTY LLC. 407-749-3075

$3,250,000

3 Beds ⋅ 4 Baths ⋅ O6444116 MLS

Welcome to 6126 Payne Stewart Drive, a beautifully renovated golf villa in Isleworth, just steps from the club house. This 2,848-square-foot home offers three bedrooms, each with its own full bathroom, plus a powder room for guests. Soaring ceilings and an open floor plan bring a sense of space to the main living areas, where travertine floors and new doors complement the recent renovations. The gourmet kitchen features a 10-ft center island and top of the line appliances. The primary suite includes a recently renovated bathroom with a generously sized shower and soaking tub. Outside, a fully fenced garden setting surrounds the pool and spa. A summer kitchen and fireplace make the space inviting for outdoor dining and relaxing in the Florida Sunshine.

6126 Payne Stewart Drive, Windermere

Listing courtesy of IRWIN REALTY GROUP LLC. 407-739-8772

6727 Merrick Landing Boulevard, Windermere

$769,000

5 Beds ⋅ 3 Baths ⋅ O6443858 MLS

Beautifully renovated home in the sought-after Vineyards at Horizons West, Windermere. This corner-lot residence has been fully updated with brand-new wood flooring throughout, a remodeled kitchen featuring top-of-the-line appliances, and fresh designer finishes on every wall. The first floor offers a dedicated home office (former 5th bedroom), while all remaining bedrooms are located upstairs. Step outside to a completely finished outdoor gourmet area, perfect for entertaining, plus a spacious backyard with synthetic turf and no rear neighbors - just a community playground across the way. The garage features durable epoxy flooring. Zoned for Independence Elementary, Bridgewater Middle, and Windermere High School, with low HOA dues that include ground maintenance. Schedule your private showing today.

6727 Merrick Landing Boulevard, Windermere

Listing courtesy of AUTHENTIC REAL ESTATE TEAM. 321-244-7676

$4,395,000

6 Beds ⋅ 6 Baths ⋅ O6443681 MLS

Set along the front nine of Isleworth’s championship golf course, the 4,739-square-foot residence has been beautifully reimagined, pairing a grand architectural presence with contemporary interiors and expansive views across the course. Beyond the private entry gate to the property, a long, dramatic drive leads to the circular motor court anchored by a distinctive tiered fountain, creating an impressive arrival to this beautifully reimagined Isleworth estate. Inside, soaring ceilings and a dramatic two-story foyer introduce beautifully updated living spaces, where new flooring, refined architectural details and distinctive backlit feature walls create a fresh, elevated aesthetic. Primary living spaces include formal living and dining rooms, a kitchen with casual dining, and a home office. The six-bedroom residence offers two bedrooms on the main level, one on the lower level and three on the upper level. The expansive primary suite is includes a large bath finished with oversized floor-to-ceiling stone tile, a freestanding soaking tub, walk-in shower and dual-sink vanity. Designed for year-round enjoyment, the outdoor living experience begins in the enclosed Florida room and unfolds onto a sprawling pool deck overlooking the golf course. A large pool is complemented by an intimate oasis dining area surrounded by a pool moat, a separate sundeck and a covered outdoor grilling area, creating multiple spaces for entertaining, dining and relaxing. With its exceptional arrival, thoughtfully renovated interiors and expansive indoor-outdoor living, this distinctive estate offers a refined setting within one of Isleworth’s most sought-after golf-course locations.

5186 Vardon Drive, Windermere

Listing courtesy of ISLEWORTH REALTY LLC. 407-909-9000

$530,000

4 Beds ⋅ 2 Baths ⋅ S5158063 MLS

This 4-bedroom, 2-bath pool home in the gated community of Eden Isle offers approximately 2,020 square feet of single-story living with an open floor plan, high ceilings, and plenty of space for both everyday living and entertaining. Step outside and enjoy your own private Florida retreat featuring a screened-in pool and a fully fenced backyard; ideal for relaxing, entertaining, or enjoying the Florida sunshine. The spacious primary suite features an en-suite bathroom with a soaking tub, separate shower, double vanity, and plenty of room to unwind. Major improvements provide added peace of mind, including a roof replaced in 2022, HVAC system replaced in 2021, and a new hot water heater. Eden Isle residents enjoy access to a community playground and private community boat ramp on Lake Speer, making it easy to enjoy the Florida lifestyle both on and off the water. Conveniently located in sought-after Windermere with easy access to shopping, dining, entertainment, major roadways, and Central Florida's world-famous attractions. Schedule your private showing today!

13738 Eden Isle Boulevard, Windermere

Listing courtesy of THE PROPERTY FIRM. 407-530-5444

$625,000

4 Beds ⋅ 3 Baths ⋅ S5157920 MLS

Under contract-accepting backup offers. The best sought-after Windermere location! This beautiful Lakes of Windermere 4 bedroom 2.5 bath home was just updated this summer with NEW ROOF, NEW APPLIANCES, NEW CARPETS, FRESHLY PAINTED INSIDE AND OUT, plus garage and floor fully painted. ELECTRIC VEHICLE CHARGER IN GARAGE. No rear neighbors: Enjoy a calm, quiet pond view from your covered 15x7 back porch. Or meet the neighbors by relaxing on your covered 17x12 front porch facing the tree-lined street! The kitchen/family room combo is light and bright with soaring 2-story ceiling and windows galore! All matching new SS appliances plus lots of wood cabinets and long breakfast bar in the kitchen that adjoins a dinette area with built in desk. All bedrooms are upstairs with new carpets. The extra large Primary suite includes a window seat, and bathroom with garden tub, separate shower, dual sinks, linen closet and private water closet. Three more comfortable bedrooms and bath are down the hall. The Lakes of Windermere community clubhouse and pool are a short walk away in addition to tennis, basketball, volleyball, and soccer courts, three playgrounds, a lake dock with fishing access, and scenic walking trails through the community including GAZEBO AT THE PINE LOOP PARK (Nobelton Drive and Mapperton Drive) a shaded space for community parties and events. Zoned for A+ rated Windermere High School! Short drive to Disney World, and close to 429 for easy access to Orlando and Horizon West for the best shopping and restaurants. Ready for immediate occupancy. Call to see it today!

12809 Holdenbury Lane, Windermere

Listing courtesy of WATSON REALTY CORP. 407-298-8800

$586,846

3 Beds ⋅ 3 Baths ⋅ TB8551016 MLS ⋅ 3 BLDG.

Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. This Cawood floor plan features interior finishes from the AW Collection Coastal, blending clean lines and neutral tones and textures. Design upgrades include 42" cabinets, quartz countertops, tiled backsplash, pendant lighting and stainless steel appliances. Ideally situated, you’re just 30 minutes from Orlando International Airport and 15 minutes from world-famous Disney theme parks. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. Residents will also enjoy a community pool and playground area. With its prime location and practical design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

13317 Lush Lime Alley, Windermere

Listing courtesy of ASHTON WOODS FLORIDA REALTY LLC. 813-918-4491

$2,995,000

6 Beds ⋅ 9 Baths ⋅ O6434168 MLS

Set on nearly an acre within the prestigious guard-gated community of Bellaria, this remarkable estate combines grand-scale living, exceptional flexibility, and an unbeatable location. Impressive curb appeal creates an immediate sense of arrival, enhanced by a spacious U-shaped driveway and an oversized three-car garage. Beyond the entry, a dramatic formal living room welcomes you with soaring two-story ceilings, abundant natural light, and an elegant bar area complete with a wine refrigerator. The expansive kitchen serves as the heart of the home, featuring a massive center island, extensive cabinetry, generous prep space, and a full suite of stainless steel appliances. A formal dining room provides a refined backdrop for special occasions, while the adjoining breakfast nook offers a relaxed setting for everyday meals. The sprawling first-floor primary suite is a private retreat with impressive proportions and separate his-and-hers walk-in closets. Its spacious bathroom features dual vanities, an oversized walk-in shower, and a soaking tub designed for relaxation. An additional guest suite on the main level provides comfort and privacy for visitors, while a dedicated formal office creates an ideal space for working from home. Upstairs, five additional bedrooms provide tremendous flexibility for family and guests. A spacious loft offers another casual gathering area, while the separate bonus room could easily be transformed into a private home theater, game room, fitness studio, or additional entertainment space. With six bedrooms, multiple living areas, and thoughtfully designed spaces throughout, the home is exceptionally well suited for both everyday living and large-scale entertaining. Outside, an expansive covered patio extends the living space and features a full summer kitchen, making it ideal for dining, entertaining, and enjoying Florida’s year-round sunshine. The enormous backyard offers remarkable possibilities, with ample room to create a custom resort-style pool. Bellaria’s prime location places you just minutes from Winter Garden Village, charming Downtown Windermere, Restaurant Row, world-renowned theme parks, and an outstanding selection of shopping, dining, and entertainment. Offering extraordinary space, privacy, and potential in one of Windermere’s most sought-after gated communities, this impressive estate presents a rare opportunity to create the ultimate luxury lifestyle.

13101 Bellaria Circle, Windermere

Listing courtesy of ONE LUXURY INTERNATIONAL LLC. 407-312-8003

$7,450,000

7 Beds ⋅ 10 Baths ⋅ O6443379 MLS

Located directly on Lake Tibet within the guard-gated community of Keene’s Pointe, this extensively updated Stonebridge custom residence blends Mediterranean-inspired architecture with transitional interiors. A long brick-paver driveway leads to a circular motor court, porte cochère, tile roof, stone accents, and arched windows. Oversized glass entry doors frame immediate lake views and open to two-story formal living spaces featuring newly installed wood flooring, detailed ceilings, clerestory windows, and abundant natural light. The kitchen includes an oversized island, quartz countertops, glazed custom cabinetry, double ovens, premium appliances, and a walk-in pantry. Open gathering areas and expansive windows provide continuous views of Lake Tibet. Additional interior features include a game room, dedicated home theater, and a private primary suite with an oversized walk-in closet and updated bathroom. Each secondary bedroom includes an ensuite bathroom. The bathrooms have been updated, the interior has been freshly painted, and the carpeting has been replaced. A detached guest house offers additional flexible living space. Added in 2019, the covered outdoor kitchen and dining pavilion features a wood-paneled ceiling, large dining and preparation island, built-in grill, pizza oven, wine cooler, and oversized refrigerator. The outdoor area also includes a resort-style pool, heated spa, expansive lawn, sand volleyball court, and soccer area overlooking the lake. A private dock with boat lift provides direct access to Lake Tibet and the Butler Chain of Lakes.

9343 Tibet Pointe Circle, Windermere

Listing courtesy of NOVA REAL ESTATE SERVICES INC. 407-592-1744

$369,000

3 Beds ⋅ 3 Baths ⋅ O6348704 MLS ⋅ Venetta Way BLDG.

Virtually Staged. Welcome home to this beautifully refreshed 3-bedroom, 2.5-bath end-unit townhome in one of Windermere’s most sought-after communities. Offering the added privacy of an end-unit location, a peaceful conservation backdrop, and a private courtyard, this home delivers the perfect blend of comfort, convenience, and easy Florida living. Freshly painted throughout with brand-new carpet, the home feels bright, clean, and move-in ready from the moment you walk through the door. The inviting layout is filled with natural light and offers plenty of space to relax, entertain, and enjoy everyday life. All three bedrooms are located upstairs, including a spacious primary suite featuring a walk-in closet, dual-sink vanity, and upgraded frameless-glass walk-in shower. Step outside to your private courtyard—a versatile outdoor space perfect for morning coffee, weekend gatherings, or unwinding at the end of the day. Beyond the courtyard, the rear of the home overlooks a conservation area, creating a peaceful natural setting with no immediate rear neighbors. It’s a rare combination of privacy and convenience. And there’s more to look forward to—a new roof is coming soon, adding another layer of value and peace of mind for the next owner. Ideally located near A-rated schools, parks, shopping, dining, and everyday conveniences, this Windermere townhome puts you close to everything while giving you a private place to call home. Come see why this one is worth making your next move!

12934 Vennetta Way, Windermere

Listing courtesy of REVEL REALTY LLC. 407-876-6448

$615,000

4 Beds ⋅ 4 Baths ⋅ O6443170 MLS

Under contract-accepting backup offers. Welcome to this 4-bedroom, 3.5-bath home in Windermere, zoned for top-rated schools including Windermere High School and Horizon West Middle School. Located near Horizon West shopping, dining, parks, and major roadways, this Windermere pool home combines a desirable location, functional layout, and the indoor-outdoor lifestyle that buyers are searching for in Central Florida.

7555 Tattant Boulevard, Windermere

Listing courtesy of BUYER REBATES REALTY. 407-629-2300

9010 Reflection Pointe Drive, Windermere

$945,000

4 Beds ⋅ 4 Baths ⋅ G5117935 MLS

Located in the desirable Windermere Trails and less than 15 minutes from Magic Kingdom, this immaculate four-bedroom 3.5-bath pool home offers an exceptional combination of style, comfort and Central Florida convenience. Unwind beside your own heated saltwater pool and spa while enjoying views of the Disney fireworks. Inside, tile flooring extends throughout the home, creating a clean and cohesive look that is both attractive and easy to maintain. Fresh interior paint in 2026 enhances the bright, welcoming atmosphere. The formal dining room makes a beautiful first impression with its gorgeous coffered ceiling, providing an elegant setting for holiday dinners, celebrations and evenings with friends. The kitchen is designed for anyone who appreciates generous workspace and exceptional storage. A substantial amount of cabinetry is complemented by expansive granite countertops, a tiled backsplash and an oversized walk-in pantry. Pendant lighting highlights the breakfast bar, creating a natural place for casual meals and conversation. Built-in stainless steel appliances and a Bosch Dacor refrigerator installed in 2022 complete this impressive space. A drinking water filtration system and a whole-house water softener add everyday convenience. The kitchen opens naturally to the spacious family room, where a stacked stone accent wall adds warmth, texture and architectural interest. Views of the pool create a beautiful backdrop and keep the indoor living areas connected to the outdoor setting. Whether hosting a crowd or enjoying a quiet evening at home, the open arrangement allows everyone to remain part of the conversation. Go outside to the heated saltwater pool and spa. With the propane heater, the pool can be enjoyed well beyond the traditional swimming season, while the space offers plenty of room for lounging, dining and entertaining. The pool filtration equipment was replaced in 2024. The thoughtfully planned four-bedroom, 3.5-bath layout provides flexibility for a family, guests or a home office. The washer and dryer (2022) are also included. A complete Bosch HVAC system, including interior and exterior equipment, was installed in spring 2024 and carries a 10-year parts/labor warranty w/required annual maintenance. The water heater is from 2019, and the exterior and tile roof were professionally power washed in 2024. An interior ADT security system and exterior CCTV camera system provide additional peace of mind. A separate two-car (with epoxy floor in 2023 and one-car garage epoxy in 2026) provides three total spaces for vehicles, storage or hobbies. Just inside one of the garages, a drop station features areas for phone charging, along with space for packages, bags and daily essentials. Windermere Trails offers a resort-style community pool, walking trails, playgrounds, pavilions, a dog park and fitness areas. Surrounded by the natural beauty of the Butler Chain of Lakes, the community is close to highly regarded A-rated schools, Lakeside Village, Hamlin Town Center, Winter Garden Village, Horizon West and the renowned dining of Dr. Phillips. Nearby SR 429 provides convenient connections to the Turnpike, SR 408 and I-4, while Walt Disney World, Disney Springs, shopping, golf, boating, restaurants and medical services are all nearby. Beautifully maintained and ready now, this home combines inviting interior spaces, a private pool retreat, recent improvements and a location that places the best of Central Florida at your doorstep.

9010 Reflection Pointe Drive, Windermere

Listing courtesy of PREMIER SOTHEBYS INT'L REALTY. 407-581-7888

$489,900

3 Beds ⋅ 2 Baths ⋅ S5157827 MLS

Welcome to 13535 Bramham Lane, a spacious and airy 3-bedroom, 2-bath, single-story home offering plenty of room to spread out and make it your own. Freshly painted throughout, the home features tile flooring in the main living areas with carpeting in the bedrooms. The versatile floor plan includes living and dining areas along with a spacious great room, providing multiple spaces for entertaining, relaxing, and everyday living. The kitchen features granite countertops and stainless steel appliances and opens to the great room, creating a comfortable gathering space at the heart of the home. Outside, nicely landscaped grounds create a welcoming first impression, while the charming front porch is perfect for morning coffee or enjoying the Florida weather. A back patio provides additional outdoor living space for grilling, entertaining, or simply relaxing. Complete with a two-car garage, this home offers a wonderful combination of space, comfort, and flexibility. Located within a gated community featuring sidewalks throughout, residents can enjoy a neighborhood setting designed for walking and outdoor living, along with a community pool. It's so close to Disney that you can hear the train whistle!

13535 Bramham Lane, Windermere

Listing courtesy of CENTURY 21 CARIOTI. 407-566-0555

$1,100,000

5 Beds ⋅ 4 Baths ⋅ O6442835 MLS

Auction Property. A Windermere address. A 24-hour guard-gated community. A home with the scale to make a statement. Tucked along a quiet cul-de-sac in the Reserve at Lake Butler Sound, this estate offers the chance to create something exceptional in a coveted setting. Soaring ceilings, architectural columns and expansive gathering spaces give the home a sense of occasion from the moment you enter. French doors open to a screened pool retreat, setting the scene for sunlit afternoons, dinner with friends and evenings under the Florida sky. Enjoy the privacy of an established luxury neighborhood with Windermere’s dining and shopping, the Butler Chain of Lakes and Orlando’s attractions within easy reach. The setting is here. The possibilities are yours.

11021 Hawkshead Court, Windermere

Listing courtesy of ACME REAL ESTATE FLORIDA LLC. 407-601-4958

$1,280,000

4 Beds ⋅ 3 Baths ⋅ O6442932 MLS

Experience the charm of Old Windermere at 104 E 1st Ave, ideally situated in the heart of one of Central Florida’s most sought-after communities. Set on an oversized 0.45-acre corner lot surrounded by mature landscaping, this beautifully reimagined single-story home offers 4 bedrooms, 2.5 bathrooms, 2,441 square feet of living space, and a 2-car garage. Transformed through an extensive renovation by Davila Homes, the residence was thoughtfully redesigned and expanded, creating the feel of a brand-new home while preserving the charm of its Old Windermere setting. The interiors showcase elevated finishes throughout, including a beautifully designed gourmet kitchen with top-of-the-line appliances, sophisticated living spaces, and carefully selected details throughout. Outside, the home embraces the Florida lifestyle with a private pool and outdoor kitchen, creating an ideal setting for entertaining, weekend gatherings, or simply enjoying the privacy and space of nearly half an acre. What truly sets this property apart is its Old Windermere location. Enjoy the character and lifestyle of living within the Town of Windermere, surrounded by tree-lined streets and just moments from local parks, dining, shopping, community events, and everything that makes this area so special—all with no HOA. Combining the character of Old Windermere with the quality, design, and finishes of a beautifully renovated home, 104 E 1st Ave offers a rare opportunity to enjoy nearly half an acre, exceptional indoor-outdoor living, and a truly turnkey residence in the heart of Windermere.

104 E 1st Avenue, Windermere

Listing courtesy of NOVA REAL ESTATE SERVICES INC. 407-592-1744

$520,000

3 Beds ⋅ 2 Baths ⋅ O6442555 MLS

Under contract-accepting backup offers. Welcome to this beautifully located single-story home in the highly desirable Windermere area! This 3-bedroom, 2-bath home offers 1,681 sq ft of comfortable living space with an open floor plan, stone countertops, walk-in closet, spacious living and dining areas, and an attached 2-car garage. Enjoy Florida living with a covered and screened patio, plus access to community amenities including a resort-style pool, clubhouse, playground, and sidewalks. Location is a major highlight! The home is zoned for highly rated schools, including Sunset Park Elementary, Horizon West Middle School, and Windermere High School, while offering convenient access to shopping, dining, entertainment, major roadways, and everything the Windermere and Horizon West areas have to offer. Offered at $520,000, this is an excellent opportunity to own a home in one of Central Florida’s most desirable locations. Schedule your private showing today!

12679 Calderdale Avenue, Windermere

Listing courtesy of NEWKEY REAL ESTATE LLC. 689-284-2468

$19,500,000

6 Beds ⋅ 10 Baths ⋅ O6441344 MLS

Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Blanche along the coveted Butler Chain of Lakes. This exceptional residence is designed for the most discerning buyer seeking luxury, exclusivity, and resort-style living on approximately 2.5 acres. Encompassing over 13,494 square feet of refined living space and more than 20,476 total square feet, the estate features six luxurious bedroom suites, eight full baths, and two half baths. Every bedroom offers oversized walk-in closets, while the primary suite is a private sanctuary complete with a sitting room, hidden passage access to the study, private morning kitchen, and direct stairway access to the lower-level fitness retreat. Designed for both grand entertaining and intimate living, the home showcases vanishing glass sliders that seamlessly connect the living room, family room, and bar area to expansive outdoor living spaces and screened terraces overlooking breathtaking sunset views across Lake Blanche. The resort-inspired outdoor setting features a heated saltwater infinity-edge pool and spa, summer kitchen, outdoor shower, and tranquil waterfront ambiance. Exceptional amenities include a full theater room with private bath, elevator servicing all three levels, extensive storage throughout, lower-level gym with steam shower and sauna-ready space, dual laundry features including a dog shower and dog door, and a separate guest house complete with living room, kitchenette, and full bath. Equipped with all-new smart-home technology and integrated systems. The gourmet kitchen is thoughtfully appointed with dual ovens, six-burner gas range, steamer, warming drawer, freestanding refrigerator and freezer, two refrigerator drawers, dual full-size dishwashers, and two microwave ovens. Completing this remarkable offering is a five-car garage, private boat dock with electric lift and jet ski slip, and an unmatched combination of sophistication, comfort, and privacy in one Of Central Florida's most prestigious golf and country club communities along the Butler Chain of Lakes.

5192 Vardon Drive, Windermere

Listing courtesy of IRWIN REALTY GROUP LLC. 407-739-8772

$645,000

4 Beds ⋅ 3 Baths ⋅ O6438323 MLS

This spacious Single-Family Home is located at the Windermere Ashlin Park, 4 bedrooms 3 full bathrooms. ?Large kitchen, bar kitchen island with basin, equipped with stainless steel appliances, closet pantry, open to breakfast nook. Family/Great room with sliding door overlooking covered patio and fenced backyard. Large laundry room with electric washer and dryer with storage cabinet. Security system installed, cable/internet distribution box . Double garage with 2 separate electric door openers. Community Pool and Club. The property is conveniently located with easy access to S.R. 535 and toll road 419. Schools, shopping areas and nearby Disney and tourist attractions.

7252 Backwoods Trail, Windermere

Listing courtesy of REALSOURCE PROPERTY MANGNT LLC. 407-298-9777

$649,000

4 Beds ⋅ 4 Baths ⋅ O6442193 MLS

Welcome to your beautiful corner lot home in the sought after Berkshire Park community of Windermere! Don’t miss the opportunity to own this thoughtfully designed 4 bedroom, 3.5-bath home with a bonus room and 3-car garage, offering an ideal blend of space, comfort, and functionality. Major updates include a new roof installed in 2022 and a new AC system installed in 2025, providing added peace of mind for the next owner. A brick-paver driveway and charming walkway welcome you to the inviting front porch, perfectly positioned along a quiet, tree-lined street. Step inside to a spacious foyer featuring soaring ceilings and an open, airy feel that continues throughout the main living areas. The formal dining room flows seamlessly into the open concept kitchen and family room, creating an ideal space for both everyday living and entertaining. The kitchen features a large center island, granite counters, stainless steel appliances, ample cabinetry, and a dedicated eat-in area, while the family room opens to a screened in patio overlooking the generously sized backyard making a wonderful setting for morning coffee, outdoor dining, or relaxing with family and friends. The main level owner’s suite offers convenience and privacy with dual vanities, tub, shower, and walk in closet. Your well appointed laundry room provides direct access to the spacious three-car garage. Upstairs, a versatile bonus room serves as the perfect media room, playroom, home office, or additional gathering space. Three generously sized bedrooms and two full bathrooms complete the second floor, providing plenty of room for family and guests. Residents of Berkshire Park enjoy community amenities including a beautiful neighborhood pool and playground, all within the highly desirable Windermere area. The close proximity to Disney World, shopping, restaurants, and "A" rated schools make this an unbeatable location. With its spacious floor plan, prime Windermere location, 3-car garage, newer roof, newer AC, and inviting outdoor living space makes this a home you won’t want to miss. Be sure to click on the virtual tours.

13324 Jervey Street, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396

$379,900

3 Beds ⋅ 3 Baths ⋅ S5157627 MLS ⋅ 8 BLDG.

LIVE IN OR INVEST WHERE OTHERS DREAM OF VACATIONING!!! Amazing opportunity in Windermere, one of Central Florida’s most desirable locations, just minutes from the magic of Walt Disney World and located in a highly rated school zone! This beautiful 3-bedroom, 2.5-bath townhouse offers the perfect combination of location, comfort, and lifestyle, featuring a spacious and functional layout plus a private fenced backyard, ideal for relaxing, entertaining, and enjoying the Florida lifestyle. Experience a beautiful community surrounded by nature and exceptional amenities, including a community pool, playground, walking trails, scenic lakes, and lush green spaces. Conveniently located near highly rated schools, shopping, dining, major roadways, and Central Florida’s world-famous attractions. Whether you’re looking for your next home or an investment opportunity in one of the Orlando area’s most sought-after locations, this is an opportunity you don’t want to miss!. LIVE IT. INVEST IN IT. LOVE WINDERMERE !!!

8608 Brookvale Drive, Windermere

Listing courtesy of AGENT TRUST REALTY CORPORATION. 407-251-0669

$349,900

3 Beds ⋅ 2 Baths ⋅ O6435895 MLS

Virtually Staged. Welcome to this spacious 3-bedroom, 2-bathroom single-story home in the gated Belmere community of Windermere. The open floor plan provides a comfortable flow between the living spaces, with a formal living room and dining room offering flexibility for entertaining, gatherings, or everyday use. The family room features high ceilings and opens to the kitchen and breakfast area, creating a central space for relaxing and spending time together. The primary suite offers a private retreat with a walk-in closet and an ensuite bathroom featuring a garden tub, separate shower, and dual vanities. Two additional bedrooms provide comfortable space for family, guests, a home office, or other needs. A screened-in patio extends the living space outdoors and overlooks the landscaped backyard. The home also includes an attached 2-car garage and convenient interior laundry area. Belmere offers residents access to community amenities including a pool, clubhouse, fitness center, tennis courts, basketball court, and playground. Conveniently located near shopping, dining, major roadways, and Orlando-area attractions, this home offers a practical layout in a desirable Windermere community.

929 Lascala Drive, Windermere

Listing courtesy of MAINSTAY BROKERAGE LLC. 800-583-2914

$689,900

5 Beds ⋅ 3 Baths ⋅ S5157579 MLS

The best family living location! Welcome home to this fabulous 5 bedrooms, 3 full baths, 2 car garage located in the peaceful community of Vineyards in Windermere Florida. Gorgeous subdivision convenient to major roadways, A+ Rated Schools, Shopping, entertainment and so much more. Just minutes away from Walt Disney World. Spacious Master ensuite with walk-in closet. Modern Kitchen with stainless steel appliances with a gas range, granite counter tops and dark wood cabinets! Screened patio with beautiful spacious view of the large yard and conservation. Community comes with a Park/playground and community pool. Do not miss this awesome opportunity!!!

6614 Bridgewater Village Rd, Windermere

Listing courtesy of MY REALTY GROUP, LLC.. 786-847-7421

$18,750,000

6 Beds ⋅ 9 Baths ⋅ O6441249 MLS

Virtually Staged. Pre-Construction. To be built. Poised on a remarkable .69-acre homesite along the shores of Lake Bessie, this exceptional new residence offers a rare opportunity to create a substantial private estate in one of Isleworth’s most coveted lakefront settings. Designed and to be built by Supreme International Construction, the residence will encompass approximately 15,337 square feet of living space across three levels, with six bedrooms, including two private primary suites, an elevator and a four-car garage accommodating up to eight vehicles with lifts. Created for both grand entertaining and effortless everyday living, the main level will feature a dramatic great hall, formal dining room, family room, expansive kitchen, private study and serene primary retreat. Soaring architectural spaces and multiple covered balconies create a natural connection to the lakefront setting. The lower level is envisioned as a private destination for leisure, with a beautifully appointed theater delivering an immersive viewing experience, complemented by a separate popcorn and snack room for added convenience and fun. A generous entertainment area, bar, summer kitchen, gym, yoga/Pilates studio, sauna and spa complete the level. The upper floor offers a second primary suite, additional bedroom suites, viewing lounge and PJ lounge. The outdoor living space is designed to maximize the breathtaking lakefront setting. Landlocked and private, Lake Bessie offers an intimate waterfront experience for boating, water sports and fishing, with no public access to the lake. This rare pre-construction opportunity offers the privilege of securing an extraordinary lakefront residence while personalizing select finishes as the residence takes shape. Within Isleworth’s 600-acre residential community, Isleworth Golf & Country Club, consistently recognized among the world’s finest private clubs, offers an exceptional lifestyle, with Membership offered separately and subject to application and approval.

5036 Latrobe Drive, Windermere

Listing courtesy of ISLEWORTH REALTY LLC. 407-909-9000

$700,000

1 Beds ⋅ 1 Baths ⋅ O6441329 MLS

Charming 1 Bedroom 1 Bath Craftsman Cottage on a spacious lot in Downtown Windermere * Whole House Natural Gas Generator keeps the lights and hot water on during all storms * Mature Oak Trees * The covered porches on the front and rear offer additional spaces to entertain, watch nature or read your favorite book while you slow down and truly experience the "Old Windermere" lifestyle * Home has been lovingly maintained and will impress even the most finicky Buyer * Don't miss this rare opportunity * Must see inside to really appreciate the home * A Garage can be added on the front and a Virtual Garage is in the pictures * there is enough room to add another Bedroom Suite in the backyard - Call for details

628 Forest Street, Windermere

Listing courtesy of VINTAGE REALTY GROUP LLC. 407-217-5458

$500,000

O6441380 MLS

Under contract-accepting backup offers. Build your dream home in Windermere. Opportunity is knocking in one of Central Florida’s most desirable areas! This spacious nearly half-acre vacant lot on Dingens Avenue in Windermere offers the perfect opportunity to bring your vision to life and build the home you have always wanted. One of the biggest advantages of this property is NO HOA! Enjoy the freedom and flexibility that comes with owning your own piece of land without the restrictions and monthly fees often associated with planned communities. Whether you envision a beautiful custom estate, a spacious family home, or a private retreat, this property gives you the opportunity to create something that is truly your own. The almost 1/2-acre size provides plenty of room to design a home with the features that matter most to you, think expansive living spaces, a beautiful outdoor entertaining area, pool, garden, garage, or whatever fits your lifestyle and vision. Instead of settling for someone else’s floor plan, start with a blank canvas and make it your own. Location is everything, and this property puts you within convenient reach of the best that the Windermere and greater Orlando area have to offer. Enjoy easy access to excellent restaurants, shopping, major highways, main roads, entertainment, and some of Central Florida’s most popular attractions. Whether you are heading out for dinner, shopping, commuting to work, or enjoying a day at one of the area’s many attractions, you will appreciate the convenience of this location. Windermere is known for its beautiful surroundings, desirable residential areas, charming community atmosphere, and proximity to everything that makes Central Florida such a sought after place to live. Opportunities to purchase a sizable homesite with no HOA in a desirable location can be hard to find. This property is competitively priced to sell, making now the time to take a serious look. Stop dreaming about the perfect home and start building it. Bring your architect, your builder, and your ideas, and turn this nearly half-acre homesite into something uniquely yours. Build what your heart desires. Make your vision come to life. Make this Windermere property the place you call home! Priced competitively to sell. Don't miss this opportunity!

Dingens Avenue, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396

$775,000

3 Beds ⋅ 2 Baths ⋅ O6441248 MLS

Professional Pics Coming Soon - They say Good Things Come in Small Packages & This Proves It * Must see this Gem to really appreciate the craftsmanship and attention to detail throughout * Completely renovated in 2020 & 2023, this exceptional Windermere property seamlessly blends timeless character with modern luxury, offering thoughtfully designed spaces, quality finishes, and an impressive level of care in every detail. From the beautifully appointed kitchen featuring Standard Sized Kitchenaid Fridge, Miele Dishwasher, Kitchenaid Gas Range, Sub Zero Double Drawer Fridge to the versatile in-law apartment every aspect of this home has been designed for comfort, functionality, and effortless Florida living * Everything was improved, the Roof, AO Smith Water Heater, Septic, A/C, Hardwood Flooring, Tile * Fireplace * Natural Gas * 1 Block from the Boat Ramp to Lake Butler and the Chain of Lakes * Downtown Windermere offers many fun events and the New Frescos Italian Restaurant, Dixie Cafe' and the Windermere Brewery are just a few places you can walk to get a great meal * Mature Landscaping and Oak Trees * 2 Covered Carports for Boat or Auto * Storage Shed with Electric provides ample room for a workshop * Book your Private Tour Now

611 Butler Street, Windermere

Listing courtesy of VINTAGE REALTY GROUP LLC. 407-217-5458

$500,000

4 Beds ⋅ 2 Baths ⋅ O6438808 MLS

Virtually Staged. Space, flexibility, and a fantastic Windermere location! Set on a prime CUL-DE-SAC LOT in the GATED Lakes of Windermere-Peachtree community, this spacious 3-bedroom + BONUS, 2-bath, 2-car garage home offers a versatile floor plan with the convenience of MAIN-LEVEL LIVING plus an oversized BONUS ROOM upstairs. A NEWER A/C (2022) adds to the appeal. Inside, you will find a welcoming foyer that opens to combined formal living and dining spaces before making your way into the kitchen that connects seamlessly with a casual dining area and spacious family room, creating an easy layout for everyday living and entertaining. Sliding glass doors extend the living space outdoors to a COVERED LANAI. Privately positioned at the back of the home, your PRIMARY SUITE features a WALK-IN CLOSET and private EN-SUITE BATH. Bedrooms two and three share a second full bath, keeping the primary living spaces, bedrooms and baths conveniently together on one level. Upstairs, the bonus room delivers valuable flexibility and can easily serve as a MEDIA ROOM, second living area, HOME OFFICE, guest space or 4TH BEDROOM. Lakes of Windermere-Peachtree offers a beautiful natural setting surrounded by trees and conservation, along with a COMMUNITY POOL and PLAYGROUND. The home is ZONED FOR “A” RATED SCHOOLS, including WINDERMERE HIGH SCHOOL, and is ideally located just off Reams Road with easy access to SR-429. Walt Disney World, Orange County National Golf Center, Four Seasons Golf & Sports Club, ESPN Wide World of Sports, shopping, dining and everyday conveniences are all just minutes away. LOCATION, LAYOUT & VERSATILITY – this Windermere home delivers all three. Call today to schedule a tour and let us say WELCOME HOME!

13424 Hopkinton Court, Windermere

Listing courtesy of WEMERT GROUP REALTY LLC. 407-214-3967

$449,000

3 Beds ⋅ 3 Baths ⋅ O6441184 MLS

Welcome to 12333 Via Derna Pl, a beautifully updated townhome located in the highly desirable Carrington community of Windermere. Offering 1,919 sq. ft. of living space, this spacious 3-bedroom, 2.5-bath home features a bright open-concept floor plan designed for both comfortable everyday living and entertaining. Recent updates to the family room, kitchen, and shared bathroom give the home a fresh, modern feel, while abundant natural light creates a warm and inviting atmosphere throughout. The property is also EV-ready, with infrastructure already in place for an electric vehicle charger. Ideally located near highly rated schools, shopping, dining, major roadways, and Central Florida’s world-famous attractions, this move-in-ready home offers an excellent combination of location, space, and modern convenience. The Tesla charger and window curtains are not included in the listing price but may be negotiated separately. Schedule your private showing and discover everything this Windermere home has to offer!

12333 Via Derna Place, Windermere

Listing courtesy of KARDOSH REALTY. 407-499-4466

$650,000

O6439608 MLS

Under contract-accepting backup offers. A rare opportunity to build your dream home in the heart of Old Windermere. This cleared, vacant parcel consists of 7 total lots being offered for the first time — a truly unique chance to secure land in the Town of Windermere before it's gone. Enjoy golf cart-friendly streets, access to the famed Butler Chain of Lakes, and the convenience of natural gas already available. With no HOA, you have the freedom to design and build exactly the home you envision. Just a short walk to downtown shops, restaurants, and community events, this homesite combines small-town charm with unbeatable convenience. Opportunities like this don't last long — bring your builder and make it yours! Lots approx. 100' x 167'. Lots 19-22: $650,000 each | Lot 18: $700,000 | Lot 29: $750,000 | Lot 30: $800,000. Multiple offers on lots 29 & 30. Highest and best by Friday, 9/18 at 5:00 pm.

618 Ridgewood Drive, Windermere

Listing courtesy of UPSIDE REAL ESTATE INC. 407-497-6345

$1,270,000

6 Beds ⋅ 5 Baths ⋅ O6431854 MLS

Experience elevated Florida living in this extraordinary 4,585-square-foot estate, ideally positioned in the heart of Windermere and just 2 miles from Magic Kingdom. Built in 2025 and presented in pristine, like-new condition, this remarkable residence offers an exceptional combination of sophisticated design, expansive living spaces, and an enviable location. Every detail has been thoughtfully considered to create a home that is as impressive as it is functional. From the moment you enter, the scale and elegance of this residence are immediately apparent. The expansive floor plan features six generously sized bedrooms, a dedicated private office, and a substantial bonus room, providing an extraordinary level of flexibility for today's lifestyle. The separate office is ideal for working from home, while the spacious bonus room can easily be transformed into a home gym, media room, children's playroom, or additional entertainment space. Upstairs, an impressive nearly 600-square-foot loft creates an entirely separate living and entertainment experience. Complete with a built-in wet bar, this remarkable space is perfectly suited for movie nights, game days, entertaining guests, or simply relaxing with family. Designed with modern luxury and everyday convenience in mind, the home features a dedicated laundry room on each floor, an abundance of additional closets, a large walk-in pantry, and generous garage space. There is no shortage of room for storage, hobbies, vehicles, and everything that comes with an elevated lifestyle. Perhaps the most exceptional feature is the location. Situated just minutes from Walt Disney World, you can enjoy the convenience of being only 2 miles from Magic Kingdom while even taking in the spectacular nightly Disney fireworks from your own home. The community also offers a playground, providing a wonderful space for children to play and enjoy the outdoors. At the same time, you'll be close to the highly sought-after Windermere school district, shopping, dining, golf, and everything Central Florida has to offer. Impeccably maintained, exceptionally spacious, and truly move-in ready, this stunning Windermere residence delivers a rare combination of luxury, convenience, and location. With six bedrooms, a dedicated office, a massive bonus room, an expansive loft with wet bar, two laundry rooms, and extraordinary storage, this is a home designed to accommodate both grand entertaining and effortless everyday living.

14360 Crest Palm Avenue, Windermere

Listing courtesy of KELLER WILLIAMS WINTER PARK. 407-545-6430

8156 Boat Hook Loop Unit 623, Windermere

$327,000

3 Beds ⋅ 2 Baths ⋅ O6439822 MLS ⋅ 8156 BLDG.

Welcome to your new home! This beautifully maintained, newly listed 3-bedroom, 2-bathroom, third-floor condo is located in the highly desirable Lakeside at Lakes of Windermere community. Offering a perfect blend of comfort, style, and convenience, this move-in-ready home is an exceptional opportunity in one of Central Florida’s most sought-after areas. Step inside to discover a thoughtfully designed interior featuring no carpet throughout, making everyday living and maintenance a breeze. The well-appointed kitchen showcases stainless steel appliances, stone countertops, a stylish backsplash, and abundant cabinet space. Ceiling fans throughout the home, including on the private balcony, add an extra level of comfort and convenience. A washer and dryer are also included. Residents of Lakeside at Lakes of Windermere enjoy an array of resort-style amenities, including a sparkling community pool, spacious fitness center, and beautifully maintained grounds—creating a welcoming environment to relax, entertain, and enjoy the Florida lifestyle. The location is truly hard to beat! Lakeside Village Center is directly across the street, putting everyday conveniences just steps from your front door. Just minutes from Walt Disney World, major highways, highly regarded schools, shopping, dining, and the charming community of Windermere, this condo offers an incredible combination of lifestyle and location. Whether you're searching for a primary residence, vacation home, or investment property, this exceptional condo checks all the boxes. Come see why this Lakeside at Lakes of Windermere gem deserves to be at the top of your list!

8156 Boat Hook Loop Unit 623, Windermere

Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS. 407-629-4420

$3,290,000

5 Beds ⋅ 7 Baths ⋅ O6439995 MLS

Welcome to an exceptional luxury residence in the prestigious gated community of Casabella in Windermere. Set on a private 0.71-acre homesite, this stunning Toll Brothers residence offers approximately 5,502 square feet of beautifully appointed living space, featuring 5 private ensuite bedrooms and 2 half bathrooms. From the moment you enter, the home impresses with sophisticated architectural details, soaring ceilings, abundant natural light, and expansive spaces thoughtfully designed for both refined everyday living and effortless entertaining. The gourmet kitchen is equipped with premium appliances, custom cabinetry, an oversized island, ample counter space, and an open-concept design that flows seamlessly into the family room and dining areas. The first-floor primary suite offers a tranquil private retreat, complete with a spa-inspired bathroom featuring dual vanities, a spacious walk-in shower, and generous his-and-her closet areas. Also located on the first floor is an additional private suite and a dedicated office, while the second floor offers the remaining bedrooms, a secondary primary suite, a spacious loft, and versatile living areas. Step outside to an impressive outdoor living space featuring a private heated in-ground pool, upgraded covered lanai with a summer kitchen, and beautifully landscaped surroundings, creating an ideal setting for entertaining or relaxing in complete privacy. Additional features include a three-car garage, tile roof, elegant finishes, abundant storage, and carefully curated furnishings throughout. Offered fully furnished, this exceptional residence presents a rare opportunity to enjoy a turnkey Windermere lifestyle within one of Central Florida’s sought-after gated communities. Ideally positioned near premier shopping, fine dining, golf, entertainment, major roadways, and world-renowned attractions, this Casabella estate brings together luxury, privacy, comfort, and convenience.

4243 Isabella Circle, Windermere

Listing courtesy of JOHN SILVA REALTY & ASSOCIATES. 407-420-7908

$2,685,000

5 Beds ⋅ 7 Baths ⋅ O6439814 MLS

Expansive golf course and water views abound from this impressive Keene’s Pointe estate residence, located on the 3rd green of the renowned Jack Nicklaus Signature Golf Course. Be welcomed by a grand foyer that flows seamlessly into a formal dining room: a refined, inviting space that blends timeless architectural character with luxury finishes. Framed by exposed wood beams, arched wall details, and wrought iron accents, the room feels warm yet grand. Nearby, the living room offers a more relaxed ambiance that elevates everyday living while providing a sophisticated backdrop for entertaining. An expansive primary bedroom and bathroom suite, office, and pool bath are located off the foyer. The chef’s kitchen feature stainless steel appliances—including a double oven and built in refrigerator—that create a seamless, upscale workflow, while the adjacent breakfast nook provides a sunlit place to enjoy morning coffee. A secondary suite on the first floor is perfect for visiting guests. Three upstairs bedroom suites share a common space for homework or socializing and a large bonus room with bar and balcony is a favorite place to entertain friends. A designated home theater is perfect for relaxing while enjoying favorite shows. Outside is a summer kitchen, fireplace, and lounge area for enjoying the Florida weather. The large resort-style pool and spa with waterfall complete the setting. Home is located across the street from the golf course driving range. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.

8142 Tibet Butler Drive, Windermere

Listing courtesy of STOCKWORTH REALTY GROUP. 407-909-5900

5373 Isleworth Country Club Drive, Windermere

$7,200,000

5 Beds ⋅ 6 Baths ⋅ O6439156 MLS

Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction. A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel. Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast. Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style. Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator. The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional golf and social membership opportunities.

5373 Isleworth Country Club Drive, Windermere

Listing courtesy of STOCKWORTH REALTY GROUP. 407-909-5900

$2,950,000

5 Beds ⋅ 4 Baths ⋅ O6439832 MLS

Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers nearly 7,000 square feet across three levels and presents a rare opportunity to renovate a true chain-of-lakes property to your own style and standards. Home retains much of its original character and is priced accordingly, creating strong value for buyers seeking premier waterfront frontage, square footage, and long-term upside in one of Windermere’s most desirable locations. Main level includes kitchen, dining area, secondary bedrooms, full baths, oversized laundry room, and sliding doors opening to covered outdoor living and lake views. A few steps down, the sunken living room features a bar, fireplace, storage, and direct water views. Upstairs, the primary suite includes a fireplace, large walk-in closet, dual vanities, tub, separate shower, and screened balcony overlooking the lake. This level also includes a private office. The lower level is a standout feature, offering a full basement living space with its own kitchen, living room, bedroom, full bath, and direct pool access, ideal for extended family, guests, or multigenerational living. An additional reinforced interior room provides flexible use as a secure safe room, storm shelter, private storage room, or secluded flex space. Outdoor features include a screened pool, covered entertaining area, fenced yard, and private dock with space for two boats and two jet skis. Garage space accommodates up to 6 cars, plus a 2-car carport and a large circular driveway that provides additional parking for guests, larger households, or recreational vehicles. Additional storage areas and the lower-level garage create excellent space for boat gear, kayaks, paddle boards, trailers, and lakefront equipment. Home is priced in line with its recent appraisal, with the value reflecting both its current condition and the renovation investment a future owner may choose to make. For buyers seeking a large lakefront footprint, multigenerational layout, extensive parking, and the ability to modernize to today’s standards, this property offers a rare value on the Butler Chain. Located minutes from downtown Windermere, Restaurant Row, golf, shopping, and major attractions.

4301 Down Point Lane, Windermere

Listing courtesy of MARIANI REALTY GROUP. 407-257-3610

$720,000

4 Beds ⋅ 2 Baths ⋅ O6439730 MLS

Under contract-accepting backup offers. Welcome to this spacious pond-front home in Providence, featuring a private screened pool and peaceful water views. Major updates include the roof, A/C system, and water heater, all replaced in 2021. Inside, the home features plantation shutters on most windows, hardwood and tile flooring with no carpet, high ceilings, and 8-foot doors throughout. The spacious primary suite overlooks the pond and provides direct access to the oversized covered lanai and pool. The updated primary bath features dual sinks, a large walk-in tiled shower with built-in bench and niches, and a spacious walk-in closet. Generously sized secondary bedrooms provide plenty of space, while the bright family room features large windows and sliding doors overlooking the pool and pond. The updated kitchen features modern cabinetry, stainless steel appliances, contemporary lighting, generous counter space, and bar seating. Step outside to enjoy the expansive covered lanai, private screened pool, mature landscaping, and tranquil pond backdrop-an inviting setting for relaxing or entertaining. Providence includes a community pool and playground. Conveniently located near shopping, dining, Winter Garden Village, major roadways, and area attractions.

6243 Andreozzi Lane, Windermere

Listing courtesy of BEYCOME OF FLORIDA LLC. 844-239-2663

$639,500

4 Beds ⋅ 3 Baths ⋅ S5157040 MLS

WATER-VIEW SETTING + NIGHTLY MAGIC KINGDOM FIREWORKS + PRIME WINDERMERE LOCATION! Welcome to 12909 Cragside Lane, a beautifully renovated 4-bedroom, 2.5-bath, 2,460-square-foot single-story home in Lakes of Windermere. Located directly across from a neighborhood pond and fountain, the home offers a uniquely Central Florida setting with nightly views of the Magic Kingdom fireworks just steps from your front door. The exceptional location also provides convenient access to highly regarded public and private schools, childcare, Horizon West amenities and Walt Disney World. This move-in-ready home has been extensively updated, with many of the major expenses of homeownership already completed. Improvements include a new roof, HVAC system, water heater, Resideo smart WiFi thermostat, interior and exterior paint, hard-surface flooring throughout with no carpet, light fixtures and ceiling fans — all in 2021; new refrigerator, range/oven, dishwasher, washer and dryer, backyard fencing, paver outdoor-living area and gazebo in 2023; new kitchen countertops and guest-bath flooring, countertop, sinks and faucets in 2025; and refreshed front and rear landscaping and AT&T Fiber wiring in 2026. The fencing, paver improvements, gazebo and landscaping were reviewed and approved through the community HOA architectural-review process. Inside, the bright and spacious floor plan features an open kitchen and family room along with additional flexible living spaces ideal for a home office, recreation, entertaining or additional gathering space. Crown molding, architectural details and updated finishes complement the extensive mechanical and cosmetic improvements throughout. The fenced backyard provides an inviting extension of the living space with its paver patio, gazebo and refreshed landscaping, while the covered front porch faces toward the peaceful pond and fountain setting. Lakes of Windermere offers a community pool, parks, playgrounds, tennis and basketball courts, sidewalks and recreational spaces. The location is especially convenient to Sunset Park Elementary, Horizon West Middle School and Windermere High School, with Windermere Preparatory School also nearby, along with multiple daycare and early-learning options approximately a mile from the home. Shopping, dining and recreation throughout Horizon West are close at hand, while Walt Disney World and Magic Kingdom are just minutes away. With its water-view setting, nightly Disney fireworks, extensive renovations, newer roof and major systems, hard-surface flooring throughout, upgraded outdoor living spaces, excellent school access, fiber connectivity and highly convenient Windermere location, 12909 Cragside Lane offers an exceptional combination of lifestyle, location and move-in-ready condition.

12909 Cragside Lane, Windermere

Listing courtesy of FLORIDA IN MOTION REALTY INC. 407-947-2757

$360,000

2 Beds ⋅ 3 Baths ⋅ O6439656 MLS ⋅ 12417 BLDG.

Welcome to the peaceful townhome community of The Lakes of Windermere, conveniently nestled just behind Walt Disney World’s Magic Kingdom! Enjoy beautiful green space out front and a tranquil conservation area in the back. The affordable HOA provides added peace of mind by covering exterior and roof maintenance, landscaping, and access to the sparkling community pool. This 2-bedroom, 2.5-bath townhome with a 2-car garage offers a flexible floor plan filled with inviting living spaces. A tiled entry foyer welcomes you into the first floor. Crown molding throughout adds an elegant finishing touch to the home’s inviting interior. The open kitchen features granite countertops, white subway tile backsplash, an undermount sink with a beautiful view, 42" wood-grain cabinetry, closet pantry and stainless steel appliances. The adjoining breakfast nook provides plenty of space for casual dining. Just off the kitchen is a separate dining room with beautiful wood flooring that could easily serve as a home office, den or flex space. The wood flooring continues into the bright and comfortable living room overlooking the private courtyard. Step outside to your fenced courtyard, complete with grass, pavers and a concrete patio area ready to accommodate your outdoor living needs. The courtyard also provides convenient access to the detached 2-car garage. Upstairs the beautiful wood flooring continues. The spacious primary suite is a true retreat. A modern barn door opens to the ensuite bath featuring dual undermount sinks, a walk-in closet, linen closet and an oversized soaking tub and shower combination. The second bedroom also offers a walk-in closet and its own private ensuite bathroom—ideal for guests, family or a roommate arrangement. An upstairs laundry area adds everyday convenience. Enjoy easy access out front to the bike/walking path that leads just over 1 mile to Lakeside Village Center, home to Publix, Starbucks, cafés, banks, recreation areas, and other everyday conveniences. The Lakes of Windermere is highly sought after for its desirable location, convenient access to high rated schools, shopping, dining, and all of the Walt Disney World parks. And with the Magic Kingdom nearby, you can even enjoy the magic of nightly fireworks right from your front door. With its flexible floor plan, private outdoor space, conservation setting, 2-car garage, and exceptional location, this townhome has so much to offer. Now is your opportunity to own a beautiful home in one of Windermere’s most convenient communities!

12417 Cruxbury Drive, Windermere

Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO. 407-622-2122

$3,300,000

4 Beds ⋅ 6 Baths ⋅ O6439554 MLS

Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations. This beautifully appointed custom residence offers nearly 4,000 square feet of living space with four bedrooms, soaring ceilings, elegant formal living and dining areas, a spacious kitchen and family room, game room, wet bar, and a thoughtfully designed split-bedroom floor plan. Rich wood and travertine marble flooring, refined architectural details, generous windows bath the main living areas with natural light, and multiple gathering spaces create an atmosphere that is both sophisticated and inviting. A whole house natural gas generator and city water provide peace of mind knowing your family is porotected during the worst Florida storms The primary suite is a private retreat, featuring a luxurious bath with spa-style amenities, a generous walk-in closet, and a serene connection to the surrounding grounds. The home's open living spaces are designed for effortless entertaining, while the separate formal areas provide an elegant setting for more intimate occasions. Outside, the property becomes a private resort. Enjoy the pool and spa surrounded by mature landscaping and expansive outdoor living areas. The private boathouse has a covered boat lift with a "Touchless" Canvas Boat cover that protects your boat from animals and the elements , 2 Jet Ski lifts, Sitting area with fan and mood lighting, Garden hose with city water for cleaning, seawall that has a small beach carved in to allow for playing in the sand of the crystal clear lake, and direct lake access make this an exceptional opportunity for boating, water sports, fishing, and sunset cruises throughout the Butler Chain. Life here extends beyond the property itself. Located on one of Windermere's most desirable paved streets, the home is just moments from the charm of historic downtown Windermere, with its tree-lined streets, local shops, restaurants, parks, community amenities, and small-town atmosphere. Residents enjoy the unique privilege of living among the lakes while remaining conveniently connected to Central Florida's premier dining, shopping, entertainment, and attractions. The Town of Windermere describes its lakes as a beloved community privilege, with the Butler Chain comprising a remarkable network of interconnected waterways. Whether you're enjoying coffee overlooking the water, entertaining beside the pool, stepping aboard your boat for an afternoon on the chain, or returning home to the peaceful canopy of mature trees, this home embodies the very best of Windermere lakefront living. Original house was built in 1961 but completely expanded and remodeled in 2000 - present owner made upgrades in 2023 - call for details

515 W 2nd Avenue, Windermere

Listing courtesy of VINTAGE REALTY GROUP LLC. 407-217-5458

$795,000

5 Beds ⋅ 5 Baths ⋅ O6438208 MLS

Under contract-accepting backup offers. Set against a natural preserve, this Windermere home combines a flexible floor plan, thoughtful upgrades, and a backyard setting that feels removed from the everyday. Natural light fills the main living spaces, while distinctive ceiling beams in the dining room add warmth and character. A full bedroom and bathroom on the first floor provide flexible space for guests, extended stays, a private office, or everyday living. Upstairs, the spacious primary suite features two custom walk-in closets designed for exceptional storage and organization. Paid-off solar panels provide added energy efficiency without an additional solar payment, while fresh front landscaping enhances the home’s curb appeal. Step outside to a backyard framed by preserve views, local wildlife, and an added sense of privacy. The home’s mid-street position also creates a more tucked-away setting from the neighborhood entrances. Conveniently located in the Windermere and Horizon West area, the home offers easy access to shopping, dining, major roadways, and Walt Disney World. It brings together comfortable living, useful spaces, energy-conscious features, and a natural backdrop that is increasingly difficult to find.

9155 Outlook Rock Trail, Windermere

Listing courtesy of SERHANT. helloflorida@serhant.com

$4,250,000

O6439500 MLS

Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 158 feet wide and one of four being carved out of a larger compound to create an extraordinary and private home site being offered for the first time. No time frame to build, no HOA approval, and a convenient location in East Windermere, bypassing downtown Windermere traffic. A rare find indeed. LOT 4 IS ALSO AVAILABLE AT THIS SAME PRICE. OTHER PRICING FOR LOTS 2 and 3 AVAILABLE BY REQUEST. *Seller unified parcels after purchase. Parcel ID reflects entire estate but only the lot noted by solid white lines is being offered for this price.

Windy Ridge Road, Windermere

Listing courtesy of STOCKWORTH REALTY GROUP. 407-909-5900

$450,000

2 Beds ⋅ 1 Baths ⋅ O6439109 MLS

Opportunity awaits at 9764 Gotha Road! This 2-bedroom, 1-bathroom home offers 1,216 square feet of living space, a private fenced yard, and NO HOA. Whether you're searching for a place to call home or looking to add another property to your investment portfolio, this home offers plenty of flexibility and potential. Inside, you'll find tile throughout the main living areas and hardwood flooring in both bedrooms. The converted garage provides additional flex space that can be utilized as a home office, game room, workout area, hobby space, or bonus room, with the laundry conveniently located within the space. Enjoy the outdoors from the screened front patio or take advantage of the wood privacy-fenced yard with room to entertain, garden, or create your own outdoor retreat. The property is serviced by a private well and septic system, features a gas water heater, and best of all-no HOA restrictions or monthly HOA fees. Located in the established Gotha area with convenient access to shopping, dining, major roadways, and surrounding Central Florida communities, this property presents an opportunity for homeowners and investors alike. Bring your vision and see the possibilities 9764 Gotha Road has to offer. Schedule your private showing today!

9764 Gotha Road, Windermere

Listing courtesy of HOMEVEST REALTY. 407-897-5400

$5,250,000

O6439497 MLS

Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 215 feet wide and one of three being carved out of a larger compound to create an extraordinary and private home site being offered for the first time. No time frame to build, no HOA approval, and a convenient location in East Windermere, bypassing downtown Windermere traffic. A rare find indeed. *Seller unified parcels after purchase. Parcel ID reflects entire estate but only the lot noted by solid white lines is being offered for this price.

Windy Ridge Road, Windermere

Listing courtesy of STOCKWORTH REALTY GROUP. 407-909-5900

$4,750,000

O6439342 MLS

Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 175 feet wide and one of three being carved out of a larger compound to create an extraordinary and private home site being offered for the first time. No time frame to build, no HOA approval, and a convenient location in East Windermere, bypassing downtown Windermere traffic. A rare find indeed. *Seller unified parcels after purchase. Parcel ID reflects entire estate but only the lot noted by solid white lines is being offered for this price.

Windy Ridge Road, Windermere

Listing courtesy of STOCKWORTH REALTY GROUP. 407-909-5900

$375,000

4 Beds ⋅ 3 Baths ⋅ O6439354 MLS ⋅ N/A BLDG.

Under contract-accepting backup offers. Virtually Staged. Welcome home to Lensdale Lane! This 4-bedroom updated townhome and move-in ready peace of mind: fresh interior paint and trim (2025), new windows and sliding glass door (2022), a newer roof (2021), new exterior paint and siding (2021), and an updated A/C (2019). Step inside to a light and bright open-concept layout where the living, dining, and kitchen flow together effortlessly. The kitchen features sleek quartz countertops, ample storage, and a breakfast bar, perfect for everyday meals or casual entertaining. The main-floor primary suite offers privacy and convenience, while three spacious secondary bedrooms and a second full bath complete the upstairs. Ceramic tile and wood laminate flooring flow throughout; no carpet anywhere! A half bath and laundry round out the main floor. Outside, enjoy your morning coffee on the privacy-fenced courtyard patio, while the covered front porch adds instant curb appeal. The 2-car rear-facing garage keeps the streetscape clean and charming. This home pairs low-maintenance living with an impressive amenity package. The HOA covers exterior maintenance and includes access to a community POOL, clubhouse, FITNESS center, sports courts and walking trails. Zoned for TOP-RATED schools: Windermere High ,Keene's Crossing Elementary, and Bridgewater Middle and just minutes from Winter Garden Vineland Rd, the 429, shopping, dining, and Central Florida's theme parks.Southbridge, part of the sought-after Summerport/Horizon West community, offers an unbeatable sense of community and lifestyle.

13730 Lensdale Lane, Windermere

Listing courtesy of NOVA REAL ESTATE SERVICES INC. 407-592-1744

5050 Isleworth Country Club Drive, Windermere

$3,189,000

4 Beds ⋅ 5 Baths ⋅ O6438618 MLS

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

5050 Isleworth Country Club Drive, Windermere

Listing courtesy of COMPASS FLORIDA LLC. 407-203-9441

$850,000

3 Beds ⋅ 3 Baths ⋅ O6439213 MLS

Under contract-accepting backup offers. Welcome to your immaculate and charming home in the heart of Downtown Windermere, where timeless traditional style meets modern convenience. Nestled beneath beautiful mature oak trees, this inviting property offers a spacious yard and a welcoming front porch perfect for relaxing in a pair of rocking chairs and enjoying the peaceful surroundings. Step through the front door into a light-filled interior featuring freshly painted walls and warm wood-look tile throughout the first floor. Your remodeled kitchen is both stylish and functional, featuring stainless steel appliances, a gas range, and granite countertops, perfect for everyday living and entertaining. Upstairs, the home showcases its original hardwood floors throughout, adding warmth and character. The spacious primary suite features a beautifully updated bathroom with custom cabinetry, walk in closets, granite countertops, and quality finishes. Two additional bedrooms and a full bathroom complete the second floor, providing plenty of space for family, guests, or a home office. The expansive, fully fenced backyard offers endless possibilities. There is ample room for a pool, playset, fire pit, outdoor games, and entertaining creating a wonderful private space to enjoy Florida’s beautiful weather. Ideally located within walking distance of the Windermere Farmers Market, local shops, restaurants, and more, with beautiful Lake Butler just blocks away, this home offers the best of the Old Windermere lifestyle. Additional highlights include a new roof installed in 2025, water softener, and newer AC unit. Don’t miss the opportunity to make this special home your own. Schedule your private showing today!

706 Oakdale Street, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396

$647,000

3 Beds ⋅ 3 Baths ⋅ O6438579 MLS

Modern elegance meets resort-style living in the Lakes of Windermere. Welcome to a beautifully renovated craftsman-style home. Thoughtfully updated for today's lifestyle, this move-in-ready residence blends timeless architectural character with modern comfort, quality finishes, and inviting indoor-outdoor living. From the moment you step inside, natural light fills open-concept living spaces, creating a bright and welcoming atmosphere throughout the home. The thoughtful layout and carefully selected finishes provide the perfect balance of style, functionality and everyday comfort. At the center of the home is a beautifully appointed kitchen designed for both everyday living and entertaining. It features an oversized 36-in professional Electrolux induction range with convection oven, a 36-inch range hood, built-in wine cooler, granite countertops, and a classic farmhouse sink. Whether preparing a casual meal or entertaining guests, the kitchen is designed to be both functional and impressive. The majestic dining room table, chairs, sideboard and barstools convey with the home as an attractive option. The primary suite includes an added layer of flexibility with a versatile suite located adjacent to the master. Use it as a nursery, private home office, fitness space, reading room, or whatever best fits your lifestyle. Step outside and discover one of the home's standout features: a private tropical-inspired outdoor retreat. The professionally landscaped backyard includes an outdoor kitchen, custom-paved seating area, and integrated LED lighting--creating an inviting setting for entertaining, outdoor dining, or simply enjoying your own private space. Recent upgrades & features include the following: Roof (2022); 2-stage AC system (2023); water-softening filtration system (2022); enclosed patio (2024); Ecobee thermostat (2022); B-Hyve automated irrigation system (2022); outdoor kitchen refrigerator (2026); luxury vinyl plank flooring (2022); and carpeting (2022). Beyond the property itself, residents enjoy access to desirable community amenities, including a community pool, tennis court, playgrounds, and a scenic fishing dock. This is a home designed for the way people live today, with beautiful interior spaces, meaningful upgrades, flexible living areas, and an exceptional outdoor environment.

7033 Bramlea Lane, Windermere

Listing courtesy of BEYCOME OF FLORIDA LLC. 844-239-2663

5379 Isleworth Country Club Drive, Windermere

$2,900,000

4 Beds ⋅ 4 Baths ⋅ O6438449 MLS

Under contract-accepting backup offers. This luxury estate in Isleworth offers a rare opportunity to remodel or create a custom estate in the highly coveted Isleworth community. Situated directly on the 17th hole of the Isleworth Country Club golf course, this property offers a unique combination of golf-course frontage and beautiful lake views. Designed for ultimate privacy, this spacious layout offers four bedroom suites each complete with a dedicated ensuite. Schedule your private tour today!!!

5379 Isleworth Country Club Drive, Windermere

Listing courtesy of LOKATION. 954-545-5583

$1,395,000

5 Beds ⋅ 4 Baths ⋅ O6437573 MLS

Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-rich home offers nearly 4,200 square feet of versatile living space just steps from Windermere's charming downtown. Situated on nearly half an acre, this five-bedroom, four-bath residence pairs distinctive architectural character with thoughtful updates, abundant natural light and exceptional flexibility. The main living level brings together the kitchen, dining area and expansive great room, where high ceilings and a striking gas fireplace create a warm and inviting gathering space. Four sets of beautiful, new sliding glass doors open to an expansive balcony overlooking the screened pool, extending the living and entertaining space outdoors. A private-entry in-law suite adds another compelling feature to this unique home, offering exceptional possibilities for multigenerational living, extended-stay guests or a private work-from-home space. This lower level includes two bedrooms, two full baths, spacious living area, and a wet bar with mini-refrigerator. The fifth bedroom, currently enjoyed as a home gym, is also perfect for an office, playroom or hobby room. Privately positioned on its own level, the generous primary suite provides a peaceful retreat with a spacious sitting area and private balcony. Recent, significant investments throughout the property include new windows and doors, three newer HVAC units, new roof September 2026, interior and exterior paint, updated astroturf in the side yard, as well as numerous other improvements, all while preserving the character and scale of this established Windermere home. The pool and patio, featuring a screen enclosure just added in 2020, and newer cabanas, perfect for entertaining, relaxing and enjoying Florida living year-round. The location offers a lifestyle all its own, with downtown Windermere’s weekly farmers market, community events, parks and small-town charm just a short walk or golf cart ride away. Town of Windermere residents also enjoy private access to a boat ramp on the renowned Butler Chain of Lakes, as well as to the town tennis and pickleball courts! Zoned for top rated Windermere Elementary and Olympia High, and situated just minutes from the shopping and dining of The Grove at Isleworth and Restaurant Row, this distinctive home delivers a rare combination of space, flexibility, and character all in a desirable, downtown Windermere location.

101 Lee Street, Windermere

Listing courtesy of STOCKWORTH REALTY GROUP. 407-909-5900

$759,000

4 Beds ⋅ 4 Baths ⋅ O6437963 MLS

Under contract-accepting backup offers. Welcome to 8104 Jailene Drive, a beautifully updated 4-bedroom, 3.5-bath pool home offering nearly 2,900 square feet of thoughtfully designed living space in the desirable Lake Sawyer community in Windermere. Set against a peaceful conservation backdrop with no rear neighbors, this home pairs privacy and outdoor living with a long list of recent improvements—including a NEW ROOF completed in May 2026, fresh interior paint and landscape lighting that beautifully highlights the property after sunset. Inside, an open, light-filled floor plan creates an easy flow for both everyday living and entertaining. The centrally located kitchen features upgraded cabinetry, Topazio White granite countertops a butler pantry, stainless steel appliances with a Bosch dishwasher, and generous workspace and storage. Custom details continue throughout the home, including upgraded wood and laminate flooring, a built-in credenza in the family room and built-in shelving in the office. The spacious primary suite offers a private retreat of its own, complete with a separate sitting area, oversized walk-in closet with built-in cabinetry. Step outside to the screened pool and enjoy a private backyard setting surrounded by mature landscaping and peaceful conservation views—an ideal place to unwind, entertain, or spend a quiet Florida afternoon. Additional conveniences include a washer and dryer, Vivant security system, and an attached 2-car garage. Some furnishings may also be negotiable. Lake Sawyer residents enjoy a community pool, basketball and tennis courts, walking trails, dog-walking areas, and more, all in a sought-after Windermere location convenient to shopping, dining, top area attractions, and everything that makes this part of Central Florida such a desirable place to call home. With significant updates already completed and an inviting indoor-outdoor lifestyle, 8104 Jailene Drive is ready for its next chapter.

8104 Jailene Drive, Windermere

Listing courtesy of CORCORAN PREMIER REALTY. 407-965-1155

$399,000

3 Beds ⋅ 3 Baths ⋅ O6437694 MLS ⋅ 14077 BLDG.

Under contract-accepting backup offers. Virtually Staged. There is something truly special about coming home to Summerport and this move-in-ready townhome captures that feeling perfectly. From the moment you arrive, the inviting front porch offers a peaceful spot to sit back and watch the sunset over Ancilla Pond. Inside, the functional main level features a highly desirable first-floor primary suite. The bright kitchen connects seamlessly to a private, fenced patio area. Upstairs, you will find an additional bedroom, a versatile loft area, and a secondary bedroom featuring a charming alcove that makes a wonderful home office or study nook. Out back, enjoy ultimate privacy with an attached garage accessed by a rear road and extended driveway. Because the property backs up to the tranquil marshland of Walsh Pond there are no rear neighbors and you are also just steps from the community playground! Summerport features resort-style amenities, including scenic walking paths, small lakes, a clubhouse pool, a fitness center, a fishing dock, volleyball, and a sand beach area right next to the tennis and basketball courts. Unbeatable Location & Convenience: * Top-Rated Schools: Just a short drive to Keene’s Crossing Elementary, Bridgewater Middle and Windermere High School. Elite private options like Windermere Preparatory School and Foundation Academy are also nearby. * Moments from Disney World and all major theme parks. * Easy Commute: Quick access to SR-429, SR-408, and the Florida Turnpike makes driving a breeze. * Shopping & Dining: Minutes from local restaurants, grocery stores, and the popular Winter Garden Village. Low-Maintenance Living, the HOA fully maintains the exterior including the lawn, exterior painting and roof replacements (new roof installed in 2022), allowing for a truly easy lifestyle. Schedule your showing today!

14077 Ancilla Boulevard, Windermere

Listing courtesy of EMPIRE NETWORK REALTY. 407-440-3798

$1,349,900

5 Beds ⋅ 3 Baths ⋅ O6436594 MLS

Virtually Staged. Set on just over an acre in Windermere, this updated 5-bedroom, 3-bath pool home offers 3,356 square feet of living space, plus a separate flex/bonus room that can be used as a media room, game room, office or additional living space. Located on a cul-de-sac in Lake Down Cove, the property offers something increasingly hard to find in Windermere: an updated home with a private pool, a flexible floor plan and more than an acre of land. Inside, high ceilings and large windows bring in plenty of natural light, while large-format marble-look porcelain tile runs throughout the main living areas. The spacious family room features a modern linear electric fireplace and opens to the kitchen and casual dining area, with views of the pool and backyard. A separate dining room is located just off the entry, and an interior Juliet balcony from the second floor overlooks the family room. The updated kitchen features dark shaker-style soft-close cabinetry, quartz countertops, a large island, farmhouse sink and glass tile backsplash. A six-burner ZLINE gas range with griddle, pot filler and stainless steel hood anchors the cooking area, along with double ovens, a microwave drawer and stainless steel appliances. Three of the five bedrooms are located downstairs, including the primary suite. The primary bedroom overlooks the pool and features crown molding, two walk-in closets and double doors leading outside. The primary bathroom includes dual vanities with quartz countertops, a freestanding soaking tub and a large frameless glass shower finished with marble-look porcelain tile. Two additional bedrooms and a second full bathroom are also downstairs, with one bedroom well suited for use as a home office. The second bathroom has direct access to the pool area. Upstairs are two additional bedrooms, a full bathroom and a separate flex room that could be used as a media room, game room, office or additional living area. The upstairs bathroom features a dual vanity with quartz countertops, a tub/shower combination and updated finishes. One of the upstairs bedrooms also features a private outdoor balcony and an interior Juliet balcony overlooking the family room below. Outside, the 1+ acre lot provides plenty of room to enjoy the property. The private pool is surrounded by a large patio with a partially covered area, while the fenced backyard offers mature trees and generous open space. The outdoor kitchen includes a built-in grill, refrigerator, sink, stone surround and counter space, and a wood-burning fire pit adds another gathering area in the backyard. Additional features include a downstairs laundry room with quartz countertops, sink and extensive cabinetry, plus an oversized two-car garage with workspace and additional storage. With five bedrooms plus a flex room, 3,356 square feet, an updated interior, private pool and more than an acre of land, this Windermere home offers an uncommon amount of space both inside and out. Conveniently located near shopping, dining, community events and major roadways, with easy access throughout Windermere and the greater Orlando area.

2540 Hempel Cove Ct, Windermere

Listing courtesy of ALIGN REAL ESTATE LLC. 305-389-2922

$445,000

3 Beds ⋅ 3 Baths ⋅ O6437967 MLS ⋅ 13048 BLDG.

Beautiful Two-Story Townhome in Windermere Sound!! Welcome to this charming two-story townhome located in the desirable Windermere Sound community. This spacious residence offers 3 bedrooms, 2.5 bathrooms, a 2-car garage, and 1,742 square feet of comfortable living space. All bedrooms are upstairs. The home features a well-appointed kitchen with stainless steel appliances, granite countertops, ample cabinet space, and a convenient layout that opens to the living and dining areas. The thoughtfully designed floor plan provides plenty of space for everyday living, entertaining, and relaxation. Windermere Sound offers a variety of amenities designed for an enjoyable community lifestyle, including a community pool, tennis and basketball courts, playgrounds, and scenic ponds. Lawn care is included, adding to the convenience of living in this well-maintained neighborhood. Ideally located near Disney World, shopping, restaurants, major roadways, and excellent schools, including Windermere High School, this townhome offers the perfect combination of space, convenience, and a desirable Windermere location. A wonderful opportunity to enjoy the comfort and convenience of living in one of the Orlando area’s most sought-after communities.

13048 Garridan Avenue, Windermere

Listing courtesy of SUNNY 365 REALTY GROUP. 407-574-7048

$1,500,000

5 Beds ⋅ 7 Baths ⋅ TB8542427 MLS

5 Bed 6 bath custom built home in gated community, 1.02 acre lot with private well for all water supply, NO water or sewer bill. Private Basketball court, overside Pool and Spa, Outdoor Kitchen hookup, granite Counter tops, built in double stainless-steel Oven, built in range. Master Bedroom 1st floor. This house also contains 2 suites, 1 on 1st Floor and another located at the 2nd floor with large screen enclosed balcony leading to the bonus room above the garage. 2nd floor also contain 2 open view lofts and theatre room. New roof in June 2023. Great location with easy access to Hwy 429, 408 and Florida Turnpike, with Schools, Supermarket, and Shopping Centers nearby. This property is also available for rent. Call today to schedule a viewing.

13503 Lake Cawood Drive, Windermere

Listing courtesy of BANNER INT'L REAL ESTATE. 407-574-5741

$699,990

4 Beds ⋅ 4 Baths ⋅ O6436893 MLS

*This home can be purchased with NO INCOME VERIFICATION.* Welcome to 13239 Jervey Street, an elegant 4-bedroom, 3.5-bath residence offering 2,745 square feet in the highly sought-after Lake Sawyer South community of Windermere. A grand entry with soaring ceilings, crown molding, and refined formal living and dining spaces sets a sophisticated tone from the start. The chef-inspired kitchen showcases granite countertops, 42-inch cabinetry, stainless steel appliances, a breakfast bar, and casual dining nook, seamlessly opening to the expansive family room—an ideal setting for both entertaining and everyday comfort. Abundant natural light extends to the screened lanai and private backyard, enhancing indoor-outdoor living. The main-level owner’s suite is a private retreat featuring generous proportions, a large walk-in closet, and a spa-style bath with dual vanities, soaking tub, and separate glass-enclosed shower. Upstairs, three additional bedrooms and a versatile loft provide flexible space for work, media, or relaxation. Additional highlights include an interior laundry room, three-car garage, extended driveway, and ample storage throughout. Residents of Lake Sawyer South enjoy community amenities including a pool, playground, sidewalks, and beautifully maintained surroundings. Ideally positioned near Horizon West, Winter Garden, premier shopping and dining, major highways, and Central Florida attractions, this home offers both convenience and lifestyle appeal. A refined Windermere address with spacious design, upscale finishes, and exceptional versatility—13239 Jervey Street delivers elevated Florida living at its finest.

13239 Jervey Street, Windermere

Listing courtesy of LPT REALTY, LLC. 877-366-2213

$600,000

4 Beds ⋅ 3 Baths ⋅ O6401590 MLS

Fresh interior/exterior paint and HVAC serviced! Residing in Summerport, this delightful home features a practical design with spacious room sizes and a tranquil pond view, providing the ideal atmosphere for everyday living and entertaining guests. Four comfortable bedrooms in tandem with multiple living areas and two covered patios offer ample space for any occasion, while granite countertops, extensive cabinetry, and custom accents throughout add an elegant touch to the interior. Summerport offers residents a list of amenities, including a clubhouse, community pool, sports courts, and multiple trails, parks, playgrounds, and dog parks for endless fun without leaving the neighborhood. Beyond these exceptional amenities, the location provides easy access to daily necessities, medical services, recreation activities, and major highways. The Summerport Village, Winter Garden Village, Shoppes at Lake Butler, and Shoppes at Windward Cay are moments away, placing numerous dining and retail needs right at your fingertips. Nearby Braddock Park and Tibet-Butler Nature Preserve provide natural beauty and outdoor activities close by, while just moments from Disney and Universal, making it ideal for those seeking both tranquil residential living and entertainment accessibility. This combination of a practical design, peaceful pond view, quality amenities, and strategic positioning creates the ideal living experience. Don't let this exceptional opportunity slip away – schedule your private showing today!

13844 Amelia Pond Drive, Windermere

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY. 407-203-0007

$645,178

3 Beds ⋅ 3 Baths ⋅ TB8544045 MLS ⋅ 2 BLDG.

Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. Interior finishes reflect the AW Collection Artisan with upgrades including 42" kitchen cabinets, quartz countertops, tiled backsplash, stainless steel appliances and luxury vinyl plank flooring throughout the main living areas. Ideally situated, you’re just 30 minutes from Orlando International Airport and 15 minutes from world-famous Disney theme parks. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. Residents will also enjoy a community pool and playground area. With its prime location and elegant design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

13325 Lush Lime Alley, Windermere

Listing courtesy of ASHTON WOODS FLORIDA REALTY LLC. 813-918-4491

$2,500,000

5 Beds ⋅ 5 Baths ⋅ S5156252 MLS

A rare opportunity to own one of just 18 custom estate homes in this exclusive Windermere enclave of Lake Davis Reserve. Set on more than half an acre, this impressive five-bedroom residence spans over 4,600 square feet, offering a remarkable sense of privacy and seclusion while remaining right in the heart of Windermere. From the moment you enter through the custom iron doors, the craftsmanship and attention to detail are unmistakable. Expansive living spaces, beautiful wood-look porcelain flooring, custom millwork and thoughtfully designed lighting create a home that feels luxurious yet exceptionally comfortable. Custom-designed fireplaces throughout the home provide striking focal points and give each living space its own sense of character and warmth. The chef's kitchen features abundant cabinetry, generous counter space, a large prep island, granite countertops, water softener and a vented cooktop, all opening seamlessly to the main living areas. The spacious primary suite is conveniently located on the first floor and offers a true private retreat, complete with its own custom fireplace, oversized walk-in shower and soaking tub. Additional generously sized bedrooms ensure everyone enjoys ample space, while upstairs, a large flex room with custom built-in cabinetry provides an ideal setting for entertaining, relaxing or movie nights. A dedicated gym adds even more versatility to the floor plan. Outside, the home's sense of privacy becomes even more apparent. A covered lanai, with wiring for remote-controlled screens, opens to a secluded backyard retreat framed by mature tropical landscaping. Completed in 2022, the heated saltwater pool features a PebbleTec finish, multicolor LED lighting, dual sun shelves and an illuminated pergola waterfall. An extended pool deck, outdoor audio, summer kitchen with natural gas, exterior bathroom and app-controlled pool and landscape lighting create an exceptional environment for entertaining or simply enjoying the Florida lifestyle in complete comfort. As evening approaches, the west-facing backyard provides beautiful sunset views in front of your patio gas fireplace. That feeling of seclusion is what makes Lake Davis Reserve so special. Despite its peaceful, private setting, the home sits in the heart of Windermere, with Windermere Preparatory School, Windermere High School and zoning for Windermere Elementary all close by. Disney, SR-429 and premier shopping and dining are just minutes away. Opportunities to purchase in Lake Davis Reserve are exceedingly rare, with only 18 custom estate homes behind its gates. Beautiful in photographs and even better in person, this is a home that simply needs to be experienced. The privacy, scale, custom finishes and atmosphere are difficult to fully capture in photographs. If your buyers are looking for luxury, security and seclusion without sacrificing the convenience of Windermere living, 5526 Marleon Drive deserves to be at the top of their viewing list.

5526 Marleon Drive, Windermere

Listing courtesy of SERHANT. helloflorida@serhant.com

$550,000

5 Beds ⋅ 4 Baths ⋅ O6437659 MLS ⋅ 9021 BLDG.

Under contract-accepting backup offers. Welcome to this beautifully appointed corner-unit townhome in the highly sought-after area of Windermere, Florida! Ideally located just 15 minutes from Walt Disney World, Hamlin Town Center, and an incredible selection of shopping, dining, entertainment, and everyday conveniences, this home offers the perfect combination of comfort, location, and lifestyle. As a desirable corner unit, the home provides added privacy and an abundance of natural light throughout. Featuring 5 bedrooms and 3.5 bathrooms, this spacious townhome offers a thoughtfully designed open-concept floor plan perfect for both everyday living and entertaining. The first floor includes a dedicated office, ideal for working from home, along with generous living and dining spaces that flow seamlessly into the kitchen. One of the home's standout features is the beautiful in-law suite, complete with its own private entrance, providing an ideal space for extended family, guests, or additional flexibility. Upstairs, the spacious primary suite offers a peaceful retreat along with a versatile loft area that can be used as a secondary living space, playroom, media area, or home gym. With three additional bedrooms upstairs, there is plenty of room for everyone. A two-car garage provides ample parking and storage, while the home's prime Windermere location puts you close to everything Central Florida has to offer. Whether you're looking for a primary residence, multigenerational living, or a fantastic investment opportunity, this townhome is a must-see!

9021 Via Di Canti, Windermere

Listing courtesy of KELLER WILLIAMS WINTER PARK. 407-545-6430

$1,159,000

4 Beds ⋅ 4 Baths ⋅ O6437718 MLS

Beautifully upgraded 4-bedroom residence featuring a thoughtfully designed floor plan, custom finishes, and exceptional indoor-outdoor living. The main level offers a private en-suite bedroom, ideal for guests or multigenerational living, along with a dedicated home office, spacious living areas, and a beautifully designed custom kitchen featuring tailored cabinetry, a large center island, integrated lighting, and generous storage. A separate TV/media room provides the perfect space for movie nights, entertainment, or relaxing with family. Upstairs, the spacious primary suite offers a private retreat with a truly special feature: Disney fireworks can be enjoyed right from the comfort of your bed. The suite also includes a generous walk-in closet and a spa-inspired primary bathroom featuring a freestanding soaking tub, dual vanities, and an oversized shower with separate his-and-hers shower fixtures. Extensive custom details can be found throughout the home, including Italian wallpaper, custom window treatments, bespoke cabinetry, decorative wall paneling, wood accents, designer lighting, and integrated LED lighting. Every element has been thoughtfully selected to create a comfortable contemporary interior. Designed for the Florida lifestyle, the outdoor living space features a spacious covered lanai with plenty of room for dining and lounging, overlooking the private heated pool and landscaped backyard. The seamless connection between the indoor and outdoor spaces makes this home equally suited for everyday living and entertaining. With a first-floor en-suite bedroom, dedicated office, media room, custom-designed kitchen, extensive interior upgrades, heated pool, and Disney fireworks views from the primary suite, this home offers an exceptional combination of style, comfort, and functionality. Thoughtfully customized and beautifully maintained, this is a home designed to be enjoyed inside and out.

12989 Westside Village Loop, Windermere

Listing courtesy of WEBB FLORIDA REALTY LLC. 407-601-0733

$519,000

3 Beds ⋅ 2 Baths ⋅ O6436938 MLS

Don’t miss the opportunity to make this beautiful home in the highly sought-after Summerport community your own! Known for its A-rated schools, picturesque surroundings, and outstanding amenities. This well-maintained 3-bedroom, 2-bath home features a versatile office/den, offering flexible space to accommodate a home office, or guest room. The home features vinyl flooring throughout with no carpet, providing a clean, stylish, and low-maintenance living environment. The kitchen is equipped with a natural gas stove, perfect for those who enjoy cooking with gas. Recent improvements include a newer roof, newer A/C system, and freshly painted exterior, offering added comfort and peace of mind. From the moment you enter the welcoming foyer, you’ll appreciate the bright and open floor plan. Two secondary bedrooms are conveniently located toward the front of the home, providing separation and privacy from the primary suite. Continue down the hallway to the spacious formal living room and flexible additional living space, perfect for adapting to your family’s needs. The private primary suite offers a relaxing retreat with a walk-in closet, dressing area, and ensuite bathroom featuring dual sinks and a spacious standing glass shower. The kitchen seamlessly connects to the bright family and dining areas, creating an inviting space filled with natural light and perfect for everyday living and entertaining. The natural gas stove adds an extra touch of convenience for the home chef. Sliding glass doors open to the covered porch, extending the living space outdoors and overlooking the spacious backyard—an ideal setting for relaxing, entertaining, or enjoying the Florida lifestyle. Summerport offers an impressive array of resort-style amenities, including a community pool, fitness center, parks, playgrounds, fishing pier, and scenic walking trails. The community’s desirable location provides easy access to Windermere, Winter Garden, and Clermont, with an abundance of shopping, dining, entertainment, recreation, and highly rated schools nearby. Commuters will appreciate the convenient access to major roadways, including Highway 429, the Florida Turnpike, SR 408 (East-West Expressway), and I-4, making it easy to travel throughout Central Florida. Walt Disney World and many of Orlando’s world-renowned attractions are also just a short drive away. For Disney enthusiasts, enjoy the added bonus of being just minutes from Walt Disney World, with the opportunity to catch the nightly fireworks from select areas within the community. With vinyl flooring throughout and no carpet, a natural gas stove, a newer roof, newer A/C, freshly painted exterior, flexible living spaces, spacious backyard, desirable location, and exceptional community amenities, this home offers an outstanding opportunity in Summerport. Schedule your private showing today and come see all this home has to offer!

4844 Flint Road, Windermere

Listing courtesy of CORCORAN PREMIER REALTY. 407-965-1155

$1,895,000

4 Beds ⋅ 5 Baths ⋅ O6437093 MLS

Under contract-accepting backup offers. Set along the shores of Lake Bessie in the heart of Downtown Windermere, this contemporary lakefront residence pairs clean architectural design with effortless single-story living. Completed in 2024, the home offers 2,868 square feet with four bedrooms, each featuring a private en-suite bath, along with a dedicated home office and an open-concept layout designed around the water views. Inside, wide-plank white oak hardwood floors, soaring ceilings and expansive black-framed glass doors create a bright, modern aesthetic while drawing the lake into the main living areas. The European-inspired kitchen anchors the home with an oversized island, quartz countertops, sleek cabinetry and smart appliances, flowing seamlessly into the dining and living spaces for easy everyday living and entertaining. The primary suite continues the home's refined design with a spa-like bath featuring a freestanding soaking tub, floating wood vanity, dual sinks and an oversized walk-in shower. Contemporary finishes and a light, neutral palette carry throughout the residence. Outdoors, a private heated pool and spa create a resort-like retreat, while the lakefront setting offers approximately 100 feet of frontage on Lake Bessie with the option to add a private dock. There is also a two car covered parking area. From morning sunrises and lake breezes to afternoons spent boating or fishing, the setting captures the relaxed lifestyle that makes Windermere so desirable. Just a short walk or golf cart ride from Downtown Windermere, the home places the weekly farmers market, parks, tennis courts, boat ramp to Lake Butler and Bessie, dining, local shops and a brewery within easy reach. Modern architecture, direct lake frontage and an exceptional in-town location come together for a rare opportunity to experience contemporary waterfront living in Windermere

930 East Boulevard, Windermere

Listing courtesy of CORCORAN PREMIER REALTY. 407-965-1155

8168 Boat Hook Loop Unit 303, Windermere

$320,000

3 Beds ⋅ 2 Baths ⋅ O6435857 MLS ⋅ 7 BLDG.

Welcome to 8168 Boat Hook Loop, Unit 303, a beautifully maintained condominium offering comfortable, low-maintenance living in a desirable community. This move-in ready residence features a spacious three-bedroom, two-bathroom floor plan designed for both everyday living and entertaining. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating a bright and inviting atmosphere. The kitchen features 42-inch upper cabinets, stone countertops, and a functional layout with ample storage and preparation space. Updates include a replaced HVAC system and hot water heater, providing added comfort and peace of mind. The spacious primary suite offers a comfortable retreat with a private en-suite bathroom and generous closet space. Two additional bedrooms provide flexibility for guests, a home office, or other lifestyle needs. Enjoy the convenience of condominium living with access to community amenities and a location close to shopping, dining, entertainment, and major roadways.

8168 Boat Hook Loop Unit 303, Windermere

Listing courtesy of SOUTHERN REALTY GROUP LLC. 407-217-6480

$410,000

3 Beds ⋅ 3 Baths ⋅ O6433201 MLS ⋅ 8641 BLDG.

Beautiful end-unit townhome in Windermere featuring the larger floor plan in the Lake Reams Townhomes community. This well-maintained 3-bedroom, 2.5-bath home offers plenty of natural light and a spacious open-concept kitchen, dining, and living area combo. The kitchen features granite countertops, tiled travertine back splash 46" wood cabinetry, and ceramic tile flooring, with kitchen and laundry appliances included. Upstairs, feel the new plush padded carpeting in the bedrooms, hallway and stairs. The spacious primary suite includes dual vanities, quartz counter top, a large walk-in closet, and walk-in shower. The guest bathroom also has a tub and shower, a single sink with a quartz counter top. Outside, enjoy a private Vinyl fenced in courtyard leading to an oversized rear-entry 2-car garage. The HOA provides low-maintenance living and includes exterior and roof maintenance, landscaping, exterior pest control, and access to the community’s Junior Olympic-size pool. Located approximately 5 minutes from Walt Disney World’s Magic Kingdom, with the added fun of being able to hear and see the Magic Kingdom fireworks each evening. Convenient to Lakeside Village, Horizon West, Winter Garden Village, shopping, dining, major roadways, and highly rated local schools. A great opportunity to enjoy a spacious Windermere townhome in an incredibly convenient location.

8641 Brookvale Drive, Windermere

Listing courtesy of LPT REALTY, LLC. 877-366-2213

$3,580,000

5 Beds ⋅ 7 Baths ⋅ O6436735 MLS

Welcome to 4302 Isabella Circle, an exceptional 5-bedroom, 6.5-bath residence offering 5,362 square feet of living space on an expansive 0.88-acre homesite within the gated Casabella community of Windermere. Offered completely furnished, this Spanish-inspired home combines generous interior living spaces with an impressive outdoor setting and water views. Inside, soaring ceilings, hardwood flooring and an expansive living area with a full wet bar create an inviting environment for both everyday living and entertaining. The open-concept gourmet kitchen features granite countertops, KitchenAid stainless-steel appliances and a gas range. The spacious first-floor primary suite offers abundant closet space and a well-appointed en suite bath, while a secondary primary suite is located upstairs along with three additional en-suite bedrooms. The fully fenced backyard is a true extension of the home, featuring an infinity-edge pool, spa, firepit, multiple lounge areas and a glass-enclosed lanai with a full summer kitchen featuring Viking appliances and a dedicated dining area. The oversized homesite provides exceptional outdoor space while maintaining beautiful water views. Additional features include a study/office with built-ins, a converted garage space currently utilized as a media/game room with the ability to be converted back, and a fully paid-off solar panel system with no remaining lease obligation. Conveniently located near shopping, dining, schools and the many amenities of the Windermere area. The combination of nearly an acre of land, extensive outdoor entertaining areas, water views, furnishings and owned solar makes 4302 Isabella Circle a distinctive offering in Casabella.

4302 Isabella Cir, Windermere

Listing courtesy of JC FLORIDA REALTY LLC. 407-257-8265

$556,256

3 Beds ⋅ 3 Baths ⋅ TB8542700 MLS ⋅ 3 BLDG.

Under Construction. This stylish two-story townhome features three spacious suites, including a second-floor primary suite and two additional bedrooms. The open-concept first floor offers a bright living area. Interior finishes feature the AW Collection Sapphire for a bold, modern style. This Cypress floor plan features a gourmet kitchen with 42” cabinets, quartz countertops, tiled backsplash stainless steel appliances, and luxury vinyl plank flooring. Enjoy a private courtyard and detached two-car garage. Located in the heart of Windermere near top-rated schools, Winter Garden Village, and charming downtown, with community amenities including a pool and playground.

13321 Lush Lime Alley, Windermere

Listing courtesy of ASHTON WOODS FLORIDA REALTY LLC. 813-918-4491

$880,000

4 Beds ⋅ 3 Baths ⋅ O6436644 MLS

Welcome to this beautifully maintained and freshly painted 4-bedroom, 2.5-bath pool home with a versatile bonus room, situated on an oversized corner lot in the gated community of Eden Isle. Residents enjoy access to a private boat ramp on Lake Speer. A spacious covered front porch leads into an open living area with views of the pool and a generously sized kitchen. Outside, the covered lanai overlooks the private salt water pool and large, fully fenced backyard. The primary suite features a tray ceiling, walk-in closet, and an updated bathroom with marble-look tile, dual vanities, a soaking tub, and frameless glass shower. Three additional bedrooms and a full bathroom are located on the opposite side of the home. The bonus room is ideal for a home office, media room, or playroom.

6309 Earthgold Drive, Windermere

Listing courtesy of REALTY HUB. 888-900-1801

$870,000

4 Beds ⋅ 3 Baths ⋅ O6436017 MLS

Windermere Custom Interior Pool Home, 4 bedroom, 2 Primary Suites, 3 full Bathrooms New Exterior and Interior paint 2026, New Hardwood Bamboo Floors 2025, Crown Molding, Coffered Ceilings. New Heated Salt Water Pool, New Air Conditioner 2025, New Hot Water Heater 2025, Gourmet Kitchen with Hand Cut European Backsplash, Butler Pantry and Walk In Pantry, New Dishwasher 2024. Remodeled Master Shower 2023. Custom Stair Railing, New Paver Front porch and Driveway. Double Pain Windows and Extra Insulated exterior Walls. Watch Disney Fireworks from your front porch. Community Pool with Cabana, walking trials, tot lot, outdoor physical fitness areas, 3 parks, dog park with washing station. Windermere High School voted top school in USA today. Elementary school in Neighborhood, Windermere Prep 3 miles, Close to Publix, Restaurants, and Theme Parks. Butler Chain Public Boat Ramp at Keene Point Park 5 minutes.

9043 Horizon Pointe Trail, Windermere

Listing courtesy of CENTURY 21 CARIOTI. 407-573-2121

$445,000

3 Beds ⋅ 3 Baths ⋅ S5156211 MLS ⋅ 11734 BLDG.

Get ready to move into one of the best homes and areas right now! Located in the thriving, serene, and highly sought-out Windermere, this dream home is one of a kind! One would never believe it, but this home is an end-unit turnkey luxury town home! Just being able to see the stunning fireworks from Disney from your beautiful home is a dream come true! The schools in Windermere are all outstanding as well, be grateful for the fact that you are living in a tranquil area with some of the best schools in Florida! Filled with several upgrades such as siding all over the garage, a summer kitchen completely fenced with vinyl fence, a filter for the water system throughout the whole house, and this is only for outside the house! This is a dream home through and through! Now entering the newly painted dream home, one will notice the wide-open floor plan with ceramic tile throughout the first floor. The kitchen has granite countertops with splash backs and stainless-steel appliances while being surrounded by several windows, take in the natural light as you cook and enjoy some great meals. Having a separate laundry room as well as a half bathroom on the first floor, enjoy the peacefulness the home brings! Going upstairs to the second floor, see the three bedrooms and two bathrooms! Both bathrooms have granite countertops as well! The master bedroom has a walk-in closet and lots of room! Don’t let this opportunity pass by, a luxurious home located in an excellent area could be yours today!

11734 Water Run Alley, Windermere

Listing courtesy of REMAX PREMIER PROPERTIES. 407-343-4245

$354,900

2 Beds ⋅ 3 Baths ⋅ O6436022 MLS ⋅ 7430 BLDG.

Virtually Staged. SOME PHOTOS HAVE BEEN VIRTUALLY STAGED. MOVE-IN READY and listed below recent appraisal - ideally located in the highly desirable Wickham Park community of Windermere! This desirable END UNIT 2-bedroom, 2.5-bath townhome offers CAREFREE, LOW-MAINTENANCE LIVING with the added benefit of its end-unit location and an outstanding setting directly across the street from expansive OPEN GREEN SPACE and an ORANGE COUNTY COMMUNITY PARK. Designed for easy Florida living, the home features a recently painted interior and a comfortable, functional floor plan with two bedrooms, each offering its own private full bath. Step outside to the PRIVATE COURTYARD connecting the home to a DETACHED TWO-CAR GARAGE—creating an inviting outdoor space with added privacy and versatility. Major improvements have already been completed, making this home truly MOVE-IN READY: HVAC replaced in 2021, NEW ROOF in 2023, exterior painted in 2024, recently painted interior, and all toilets replaced in 2026. Wickham Park residents enjoy desirable COMMUNITY AMENITIES, including a COMMUNITY POOL and CLUBHOUSE, along with a sought-after Windermere location convenient to Walt Disney World, Orlando theme parks and attractions, shopping, dining, entertainment, schools, and major Central Florida roadways. Enjoy the best of the FLORIDA LIFESTYLE with the convenience and ease of low-maintenance townhome living. Whether you're searching for a PRIMARY RESIDENCE, SECOND HOME, or simply a low-maintenance Windermere home close to Disney and Orlando's world-famous attractions, this END-UNIT townhome delivers LOCATION, CONVENIENCE, OUTDOOR SPACE, and CAREFREE LIVING. With the big-ticket updates already completed, all that's left to do is move in and enjoy. Schedule your private showing today!

7430 Bentonshire Avenue, Windermere

Listing courtesy of EXP REALTY LLC. 888-883-8509

$775,000

4 Beds ⋅ 3 Baths ⋅ O6436040 MLS

Welcome to 8291 Procida Isle Lane, a stunning ONE-STORY 4 bedrooms, 3 full bathrooms POOL home with a TILE roof and 2-car garage in the highly sought-after Windermere Isle community. Offering 2,224 square feet of beautifully designed living space, this meticulously maintained home combines modern upgrades, everyday comfort, and an incredible backyard retreat. The heart of the home is the gourmet kitchen featuring a LARGE island with quartz countertops with seating for four, modern pendant lights, gas cooktop, stainless steel Whirlpool appliances with built-in oven, 42-inch cabinets with crown molding, and a large pantry. WOOD LOOK TILE flows throughout the main living areas, while the bedrooms feature luxury vinyl plank flooring. The spacious primary suite features a tray ceiling, walk-in closet, and a beautifully upgraded en-suite bathroom with DUAL vanities and an OVERSIZED walk-in shower. The home has been freshly painted inside and out with Sherwin Williams Emerald, including designer accent walls in the hallway and patio, and the entire exterior and roof have been recently pressure washed. Step outside and discover your own private resort-style oasis! The HEATED SALTWATER POOL, built in 2021, features a tanning shelf with two submerged loungers, bubbler fountains, and a stunning WATERFALL surrounded by a natural stone patio. A wood pergola with café lighting creates the perfect outdoor seating area. As the sun goes down, tiki torch landscape lighting sets the mood for evenings around the fire pit. Also, you can enjoy the DISNEY FIREWORKS from your own backyard! Additional upgrades include solar panels to help reduce electric costs, a whole-house WATER FILTRATION SYSTEM and WATER SOFTENER, TESLA EV charger in the garage, and SMART HOME features including a smart thermostat, doorbell, locks, and garage control. Washer, dryer are included. Located in Windermere Isle with a community pool and low HOA which includes cable TV and Internet, this home is just minutes from Hamlin Town Center, the 429, shopping, dining, and Disney parks. Whether you're looking for a forever home or a Florida retreat, this exceptional property offers the perfect combination of luxury, outdoor living, and location. Schedule your private showing TODAY!

8291 Procida Isle Lane, Windermere

Listing courtesy of KELLER WILLIAMS REALTY AT THE LAKES. 407-566-1800

$1,495,000

5 Beds ⋅ 5 Baths ⋅ O6435610 MLS

Under contract-accepting backup offers. Coming Soon! Located in the exclusive Reserve at Lake Butler Sound — one of Windermere’s premier 24-hour guard-gated communities — this custom 5-bedroom, 4.5-bath pool home offers 4,238 square feet of living space, four bedrooms on the first floor, exceptional indoor-outdoor living, and a prime Windermere location near the renowned Butler Chain of Lakes. Situated on an oversized cul-de-sac homesite and set back from the street, a long private driveway and new water feature create an impressive sense of arrival. Inside, soaring ceilings, architectural columns, graceful archways, crown molding, and abundant natural light create an elegant yet comfortable atmosphere, with views from the main living areas to the pool beyond. Formal living and dining rooms provide plenty of space for entertaining, while the spacious family room features a gas fireplace and built-in entertainment area. The generously sized kitchen offers granite countertops, extensive cabinetry and counter space, a center island, 6-burner gas cooktop, stainless steel appliances, and casual dining overlooking the pool. The flexible first-floor layout includes four bedrooms, including the primary suite. A private office with built-in bookcases overlooks the front of the home, while an additional flex space adjoining the primary suite is ideal for a second office, exercise room, den, or sitting area. All bedrooms are generously sized, and two secondary bedrooms enjoy adjoining bath access. The spacious primary suite overlooks the pool and features a spa-inspired bath with dual vanities, large walk-in shower, jetted soaking tub, and dual closets. Upstairs, the private fifth bedroom/bonus suite is currently used as a theater room and includes its own bathroom and walk-in closet. At approximately 24 feet long, this versatile space could also serve as a game room, guest suite, home gym, or oversized bonus room. Outside, the expansive screened pool and spa area offers multiple spaces for relaxing and entertaining. A covered lanai and outdoor kitchen create the perfect setting for year-round Florida living. Many major components have already been replaced or improved, including a newer roof, new septic drainfield (2021), pool resurfacing (2021), pool heater (2021), AC (2024), hot water heater (2025), and a new security camera system (2025). Reserve at Lake Butler Sound is known for its beautiful streetscapes, estate homes, neighborhood parks, and community fishing pier with access to Lake Butler and the Butler Chain of Lakes. Ideally located near Windermere shopping and dining, Restaurant Row, major roadways, golf, and Central Florida attractions. Zoned for Windermere Elementary, Bridgewater Middle, and Windermere High School and convenient to area private schools. Offering an exceptional combination of space, flexibility, major improvements, and an exclusive guard-gated Windermere setting, this is a home you’ll want to see. Coming soon — more details and professional photography to follow!

6239 Rydal Court, Windermere

Listing courtesy of INFINITY REALTY GROUP LLC. 407-234-2256

$990,000

4 Beds ⋅ 3 Baths ⋅ O6435494 MLS

Completely renovated Gotha/Windermere retreat with NO HOA—bring your boat, RV, or camper! This rare property features a light-filled 3BR/2BA main home with living, dining, and family rooms, PLUS a private detached 1BR/loft in-law suite complete with a kitchenette and living space. Ideal for multi-generational living or private guest quarters! Fully updated from top to bottom: new stucco-finished block construction, spray-foam insulation, new roof with solid wood decking, new siding, soffits, gutters, and a brand-new septic system and drain field. Enjoy the sprawling, fully fenced backyard shaded by towering mature oaks, featuring a custom paver patio and storage shed. Walk to Gotha Park (tennis, playground, pavilion) or stroll with your dog to Yellow Dog Eats. Zoned for top-rated Thornebrooke Elementary, with quick access to Disney, dining, and major highways. Modern peace of mind meets country charm—schedule your tour today!

1243 Dingens Avenue, Windermere

Listing courtesy of REALMULTIPROPERTY LLC. 407-412-8598

$560,000

3 Beds ⋅ 2 Baths ⋅ O6435175 MLS

Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2-bath home situated on an oversized lot in the established Silver Woods community of Windermere. The heart of the home is the spacious kitchen featuring solid wood cabinetry, stainless steel appliances, marble countertops, and an impressive center island offering plenty of workspace and storage. The kitchen opens to the living and dining areas, creating a comfortable and functional layout for everyday living and entertaining. An additional flex space provides the perfect option for a home office, den, playroom, or additional living area. The spacious primary suite features both a walk-in and additional closet, along with an updated en-suite bath with dual vanities, granite countertops, and marble flooring. The split-bedroom floor plan offers two additional bedrooms and an updated guest bath. Outside, enjoy a massive fully fenced backyard with plenty of privacy and room to entertain, play, garden, or create your own outdoor oasis. The oversized lot is a standout feature and offers endless possibilities. Located in the established Silver Woods community in the heart of Windermere, enjoy a peaceful neighborhood setting surrounded by mature landscaping while still being conveniently located near Downtown Windermere, Restaurant Row, Winter Garden Village, Downtown Winter Garden, shopping, dining, schools, major roadways, and Orlando’s world-famous attractions. Silver Woods also offers community amenities including tennis courts. A wonderful opportunity to enjoy the Windermere lifestyle in the highly desirable 34786 area!

5125 Sun Palm Drive, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396

$200,000

S5156135 MLS

Great investment opportunity!

Park Ridge Gotha Road, Windermere

Listing courtesy of OLYMPUS EXECUTIVE REALTY INC. mls@oerfl.com

$964,500

5 Beds ⋅ 3 Baths ⋅ O6435449 MLS

Under contract-accepting backup offers. YOUR SEARCH IS OVER! NOW AVAILABLE! Exceptional custom CAHILL pool home situated on a private sprawling .92 acre oversized lot in the highly desirable Willows at Lake Rhea in the Town Limits of Windermere. Offering 5 bedrooms, 3 bathrooms, the thoughtfully designed split floor plan provides an ideal balance of privacy, comfort and functionality. The home features elegant formal living and dining spaces , perfect for entertaining guests or enjoying special occasions. A warm wood burning fireplace serves as a beautiful focal point, creating a cozy atmosphere for relaxing with family and friends. The spacious 3 car garage provides ample room for vehicles, storage, and recreational equipment. An expansive outdoor space in complemented by a sparkling pool area creating a private retreat ideal for entertaining and enjoying Florida's year round lifestyle. Home is zoned for highly regarded schools including Windermere Elementary (walk, bike, golf cart), Bridgewater Middle School and Windermere High School. Conveniently located near world class attractions, premier shopping, dining and entertainment, this property offers the perfect combination of tranquility and accessibility. New roof in 2018. Don't miss your opportunity own a home for under $1 million dollars in this highly sought after and desirable WIndermemre neighborhood. Professional pics to come!

11348 Willow Gardens Drive, Windermere

Listing courtesy of VINTAGE REALTY GROUP LLC. 407-217-5458

$1,695,000

5 Beds ⋅ 5 Baths ⋅ S5156040 MLS

Welcome to this iconic Arthur Rutenberg custom estate offering 5 bedrooms, 4.5 baths, plus a private executive office with approximately 4,219 sq ft of refined living space on a rare 0.47-acre lot. Crafted with soaring ceilings, elegant tile flooring throughout the public areas, and rich hardwood floors in the bedrooms, custom millwork, plantation shutters, and designer marble and onyx finishes throughout. The gourmet kitchen is built for entertaining with custom cabinetry, large center island, stone countertops, and premium Viking and Miele appliances. The home offers two private primary suites including a spacious primary suite and a separate in-law master suite, each with spa-like en-suite bath, plus two additional bedrooms connected by a Jack-and-Jill bath. Additional highlights include a dedicated private theater room, elegant wet bar with wine cellar, and a executive office. Resort-style outdoor living features a screened saltwater pool and heated spa, outdoor kitchen, fireplace and TV, perfect for year-round Florida entertaining. Recent Capital Improvements include two new Carrier Infinity HVAC systems, new gas tankless water heater, new irrigation system, new pool pump and heater, whole-home advanced security, and integrated Sonos sound system.

1480 Hempel Avenue, Windermere

Listing courtesy of AROD PARTNERS REALTY. 407-627-7621

$575,000

4 Beds ⋅ 3 Baths ⋅ O6435655 MLS

Welcome to this beautifully fully renovated Windermere home, where every room has been thoughtfully updated to create a fresh, modern, move-in-ready living experience. Located in the desirable Preston Square community, this 4-bedroom, 3-bath home offers a convenient location near Sunset Park Elementary, Horizon West Middle and Windermere High, along with easy access to shopping, dining, entertainment and the growing Horizon West area. With stylish updates throughout and an excellent Windermere location, this is a home you won’t want to miss!

6828 Helmsley Circle, Windermere

Listing courtesy of LPT REALTY, LLC. 877-366-2213

$760,000

5 Beds ⋅ 4 Baths ⋅ O6433322 MLS

Under contract-accepting backup offers. Water-view. Welcome to 12832 Westside Village Loop, an exceptional Windermere residence offering an impressive combination of space, location, privacy, views, and highly desirable schools. Built in 2018 and offering approximately 3,705 square feet of living space with 5 bedrooms and 4 full bathrooms, this beautifully designed home provides a spacious and versatile layout ideal for both everyday living and entertaining. What truly sets this property apart is its unique lot positioning and open surroundings. Situated on an approximately 8,975-square-foot lot, the home enjoys a desirable open rear and side setting with peaceful pond views and significantly more visual openness than a typical interior lot, creating an enhanced sense of privacy, space, and tranquility. The irregular lot configuration and expansive green space surrounding the property provide a rare feeling of separation from neighboring homes and make the outdoor setting an exceptional feature of this residence. Beyond the property itself, the location is outstanding—nestled within the sought-after Westside Village community in Windermere, with convenient access to shopping, dining, Disney, major roadways, and the rapidly growing Horizon West area. The home is also currently zoned for the highly desirable Bay Lake Elementary, Horizon West Middle School, and Windermere High School, with Horizon West Middle exceptionally close to the community. Combining a distinctive lot, beautiful pond and open-space views, added privacy, generous living space, excellent schools, and a premier Windermere location, this property delivers a combination that is increasingly difficult to find in Central Florida.

12832 Westside Village Loop, Windermere

Listing courtesy of INTEREALTY SERVICE. 626-328-8535

$3,599,000

5 Beds ⋅ 7 Baths ⋅ O6432946 MLS

EXCEPTIONAL LAKEFRONT LUXURY ESTATE IN CASABELLA AT WINDERMERE Discover an extraordinary luxury residence in the prestigious gated community of Casabella at Windermere, where elegant architecture, exceptional outdoor living, and one of the community’s most desirable lots come together. The true highlight of this property is its exceptional waterfront setting. The lake beautifully surrounds the rear of the home, pool, and outdoor living areas, creating a rare sense of privacy and tranquility. From the expansive covered lanai and upper-level balcony, enjoy breathtaking water views and a peaceful backdrop that makes this property truly special. Featuring two spacious levels and soaring ceilings, this magnificent home offers approximately 5,073 square feet of luxurious living space with 5 bedrooms, all featuring private en-suite bathrooms and walk-in closets. The primary suite is conveniently located on the first floor and offers a spa-inspired bathroom, large windows, and a serene connection to the outdoor surroundings. The gourmet kitchen combines functionality and elegance with modern wood cabinetry, stainless steel appliances, and generous counter space, creating an inviting space for both everyday living and entertaining. The open living areas feature impressive proportions and abundant natural light, perfectly complementing the home's sophisticated Mediterranean-inspired architecture. Step outside to your private resort-style retreat. The expansive outdoor living area features a private pool, heated spa, and spacious gourmet summer kitchen, creating the perfect setting for entertaining guests or enjoying relaxing evenings overlooking the lake. From the elegant façade and impressive two-story design to the spectacular waterfront setting and exceptional outdoor living spaces, this residence offers a rare combination of luxury, privacy, and breathtaking views. Located in Casabella at Windermere, a prestigious gated community known for its spacious homesites and elegant residences, the property is conveniently located near premier shopping, dining, top-rated schools, major roadways, and Orlando’s world-famous attractions. A truly remarkable opportunity to own a one-of-a-kind luxury estate in one of Windermere’s most desirable communities.

3986 Isabella Circle, Windermere

Listing courtesy of WRA BUSINESS & REAL ESTATE. 407-512-1008

$410,000

3 Beds ⋅ 3 Baths ⋅ O6430411 MLS ⋅ 11425 BLDG.

Location, lifestyle, and move-in-ready convenience come together in this beautifully maintained 3-bedroom, 2.5-bath townhome in the highly desirable Windermere/Lake Burden community. Perfectly positioned directly across from the community pool, this home offers the ideal combination of comfort, style, and resort-inspired living. A charming covered front porch welcomes you inside, where you'll find a bright, open floor plan featuring tile flooring throughout the main level and a versatile flex room that makes the perfect home office, study, playroom, or additional living space. The spacious living room is filled with natural light and features elegant French doors that open to your private outdoor retreat. The well-appointed kitchen is designed for both everyday living and entertaining, showcasing solid surface countertops, stainless steel appliances, abundant cabinetry, and a large center island with breakfast bar that overlooks the main living area. Step outside to your own private, fenced brick-paver courtyard, an ideal space for morning coffee, evening gatherings, or relaxing outdoors. The detached two-car garage provides ample parking and additional storage. Living in Lake Burden means enjoying an exceptional lifestyle with amenities just moments from your door, including a resort-style community pool, clubhouse with kitchen and lounge, tennis courts, trails, fishing pier, boardwalk, playground, softball field, picnic areas, and beautiful Lake Burden. Whether you enjoy an active lifestyle or peaceful evenings by the water, this community truly has something for everyone. Conveniently located just minutes from Disney, Winter Garden Village, Downtown Windermere, top-rated schools, shopping, dining, and major highways, this home is ideal as a primary residence, second home, or investment property. Offering prime location, flexible living space, a private courtyard, two-car garage, this is a rare opportunity to own a move-in-ready home in one of Central Florida's most sought-after communities. Mortgage savings may be available for buyers of this listing. Schedule your private showing today!

11425 Brownstone Street, Windermere

Listing courtesy of REDFIN CORPORATION. 407-708-9747

$2,240,000

4 Beds ⋅ 6 Baths ⋅ O6434011 MLS

Welcome to Keene’s Pointe - 24-hour gated/attended golf community situated around The Golden Bear Club, an 18-hole Jack Nicklaus golf course featuring golf, tennis, fitness, dining and swimming. This custom home positioned on a private lot overlooking the sixth hole offers single-story living with a split floor plan. Designed with function in mind, the primary suite and office are situated on one side for added privacy, while three additional bedroom en-suites and the laundry room are located on the opposite side. A double-door invites you into the formal living and dining room with wet bar. Quality finishes throughout, including 8-foot interior doors, custom woodwork and detailed ceiling designs, custom drapes and power blinds, camera system, and much more. The kitchen is equipped with stainless appliances, granite countertops, cooking island, spacious breakfast bar, a hidden walk-in pantry, and a built-in desk area. The family room features a stone gas fireplace with built-in cabinetry and flows naturally into the bonus room with half bath boasting beautiful wood paneled walls, perfect for use as a media room, playroom, or game room. The primary suite includes a sitting area, a 16x13 custom closet, and a well-appointed bathroom with jetted tub, walk-in shower, and dual vanities with makeup area. The office features built-in cabinetry and classic wood detailing. Outdoor living is designed for entertaining and functionality, with heated pool and spa with rock waterfall and fountains and summer kitchen with grill, sink and an area for a beverage refrigerator. The fenced back yard is private with a putting green, mosquito misting system and fire pit. Enjoy nightly Disney fireworks visible from the living room, primary bedroom, kitchen, and outdoor living space. The low-maintenance exterior combines stucco and stone finishes, complemented by a paver driveway and a three-car side-entry garage. Conveniently located to shopping, dining, expressways, tourist attractions and top-rated public and private schools, this highly desired community has it all!

6102 S Hampshire Ct, Windermere

Listing courtesy of SOUTHERN REALTY GROUP LLC. 407-217-6480

$969,000

5 Beds ⋅ 5 Baths ⋅ O6434228 MLS

WELCOME HOME ! WELL MAINTAINED , LARGE, 5 BEDROOM, 4 BATH HOME . ALSO INCLUDES OFFICE, MOVIE ROOM , STORAGE ROOM AND LOFT. OVERSIZE 3 CAR GARAGE,BRICK PAVER DRIVEWAY AND PATIO. FEATURES POOL AND POND WITH WATER FOUNTAIN. CLOSE TO MILLENNIA MALL,DOWNTOWN ORLANDO ,RESTAURANT ROW,DISNEY,UNIVERSAL,PARKS AND RECREATION. NO REAR NEIGHBORS AND QUIET NEIGHBORHOOD. KITCHEN FEAUTERES ISLAND, UPGRADED STAINLESS STEEL APPLIANCES, GRANITE COUNTER TOPS AND LARGE WALK IN PANTRY. DONT MISS OUT !

9609 Westover Club Circle, Windermere

Listing courtesy of ALPHA R.E. OF CENTRAL FL LLC. 407-927-1040

$2,299,000

5 Beds ⋅ 6 Baths ⋅ O6434392 MLS

Welcome to this beautiful, unique, and modern luxury home, built in 2023 and nestled on a generously sized, secluded lot in the highly sought-after and exclusive City of Windermere. Known for its lush natural landscapes, scenic trails, recreation parks, charming local shops, restaurants, beautiful lakes, top-rated schools, and exceptional quality of life, Windermere offers a truly desirable place to call home. This exceptional property also includes a 1/24th ownership interest in private deeded lakefront property, located directly across the street, featuring Lake Butler Chain of Lakes access, a private dock, and boat ramp. Enjoy the peaceful surroundings and beautiful lake views right from your home—and take advantage of this rare opportunity to enjoy lakefront view in Windermere. Step inside and discover an impressive open-concept layout with integrated formal living and dining areas, creating a spacious and inviting atmosphere. The stunning kitchen features upgraded appliances, sleek flush cabinetry, and a spacious walk-in pantry, making it both stylish and highly functional. This one-of-a-kind residence offers 5 bedrooms, including 4 private bedroom suites, each with its own bathroom. There is a main suite on each floor, providing exceptional flexibility and privacy. The upstairs main suite is a true retreat, complete with a large private balcony overlooking a beautiful lake view—perfect for relaxing and enjoying the serene surroundings. Another outstanding feature is the convenience of two laundry areas: a full laundry room on the first floor and a laundry closet upstairs. The home showcases cutting-edge modern design and upgraded finishes throughout, including: • Designer lighting features throughout the home, controlled by smart switches from your phone • Striking floating staircase • Durable TPO roofing • Energy-efficient foam insulation • Oversized premium JELD-WEN windows • High-quality PGT sliding glass doors • Modern finishes and thoughtful upgrades throughout Every detail has been thoughtfully designed to combine luxury, comfort, technology, and functionality. Stop searching—you’ve found your dream home among the lakes!

11113 Lake Butler Boulevard, Windermere

Listing courtesy of QUATTRO R E SOLUTIONS LLC. 407-278-8991

$998,999

6 Beds ⋅ 5 Baths ⋅ O6433721 MLS

Two full owner's suites, one on the main level and one upstairs, set this Windermere Trails residence apart. The main-floor suite offers a private en suite bath with dual sinks, a separate soaking tub and shower, and a skylight, making it a true in-law or multigenerational retreat. Upstairs, a second owner's suite anchors a private wing with its own en suite bath and walk-in closet. At 4,507 square feet, the home offers six bedrooms and four and a half baths across two levels. The kitchen centers the main living space with double wall ovens, stainless appliances and a large island open to the dining and gathering areas. Upstairs, a second living area adds flexible space for work, recreation or a home office, alongside a Jack-and-Jill suite and two additional bedrooms. French doors open to a screened and covered lanai overlooking the fenced backyard, extending the living space outdoors. Set on a 10,395-square-foot corner lot, the home is zoned for Bay Lake Elementary, Horizon West Middle and Windermere High School, with community pool, playground and pavilion access. Built in 2014. Engineered hardwood and tile throughout.

8701 Iron Mountain Trail, Windermere

Listing courtesy of KELLER WILLIAMS CLASSIC. murraycoleman@kw.com

$528,000

3 Beds ⋅ 3 Baths ⋅ C7529514 MLS ⋅ 2014 BLDG.

This beautifully renovated 3-bedroom, 2.5-bath luxury home in a prime Windermere location offers the perfect blend of modern elegance, comfort, and peaceful Florida living. The bright open-concept layout creates a seamless flow between the living, dining, and kitchen areas, ideal for both everyday living and entertaining. Recent renovations include new stairs with sleek glass railings, beautifully updated bathrooms, a smart bidet toilet, and new appliances, giving the home a fresh feel, while the downstairs showcases beautiful high-gloss tile flooring that adds to the bright, upscale atmosphere. Upstairs, an additional flex/living area offers the perfect space for a home office, yoga studio, reading retreat, or lounge. One of the home’s standout features is the expansive upstairs balcony, accessible from two bedrooms and overlooking the lake, where you can enjoy your morning coffee or unwind surrounded by mature trees, birds, and nature in a wonderfully quiet setting. The home also features a two-car garage and is conveniently located near the best schools, shopping, dining, entertainment, major roadways, and everyday amenities. With its lake views, open-concept design, extensive updates, flexible living spaces, peaceful natural surroundings, and sought-after Windermere location, this move-in-ready home offers an exceptional combination of luxury, tranquility, and convenience.

8630 Powder Ridge Trail, Windermere

Listing courtesy of SUNCOAST CHOICE REALTY. 516-476-8730

2031 Willow Lauren Lane Unit L, Windermere

$1,179,000

5 Beds ⋅ 5 Baths ⋅ O6429898 MLS

Stunning William P Campbell custom home on a private, oversized lot of more than half an acre in one of the most desirable communities in the Town of Windermere-Willows at Lake Rhea! From the moment you arrive, the soaring 14-foot ceilings, abundant windows, and elegant glass French doors create a light-filled, inviting atmosphere with beautiful views of the pool and spa from nearly every room. Mature landscaping surrounds the property, creating a peaceful and private setting that is increasingly rare. Designed for both sophisticated entertaining and comfortable everyday living, the open-concept layout seamlessly connects the living room, dining room, gourmet kitchen, and family room, creating an exceptional space for gatherings. The chef’s kitchen is truly the heart of the home, featuring an induction cooktop, Wolf double ovens, Sub-Zero refrigerator, Bosch dishwasher, brand-new disposal, upgraded granite countertops, farmhouse sink, prep sink and an abundance of custom cabinetry for exceptional storage. The expansive private primary suite overlooks the sparkling pool and spa and offers two oversized walk-in closets. The luxurious primary bath features a massive walk-in-shower with dual shower heads, jetted tub, and an impressive dual vanity. Two additional generously sized bedrooms share a Jack-and-Jill bath, while the fourth bedroom offers privacy and direct access to the pool bath-perfect for guests. Upstairs an oversized bonus room/fifth bedroom provides incredible flexibility and includes a full bath and wet bar, making it an ideal guest suite, media room, office, or entertaining space. Step outside to your private pool and spa and enjoy the Florida lifestyle in complete comfort, with a fabulous outdoor kitchen, creating the perfect setting for al fresco dining and entertaining. This exceptional home is truly move-in ready with a new roof in 2016, newer AC systems in 2021 and 2026, and a repipe completed in 2024. A three-car side-entry garage, expansive brick-paver driveway, and circular drive provide impressive curb appeal and abundant parking. Enjoy all the benefits of living in the Town of Windermere, including access to the Butler Chain of Lakes boat ramp, weekly Farmers Market, Public Library, and year-round community events. Willows At Lake Rhea offers an exceptional setting within one of Windermere’s most desirable communities, combining an outstanding custom home, a rare oversized private lot, and the lifestyle, charm and amenities that make Windermere so sought after.

2031 Willow Lauren Lane Unit L, Windermere

Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO. 407-622-2122

$975,000

3 Beds ⋅ 3 Baths ⋅ O6433478 MLS

Welcome to this beautifully updated home situated on a full 1-acre homesite in a highly desirable, established community surrounded by mature trees. Enjoy access to the Butler Chain of Lakes for just $100 annually, offering an incredible opportunity for boating, fishing, and the Florida lake lifestyle. Inside, the home features a spacious open layout with an updated kitchen, white cabinetry, stone countertops, stainless-steel appliances, and a large island overlooking the living area. A rare double primary suite configuration provides exceptional flexibility for guests, multigenerational living, or a private retreat. The home also offers three full bathrooms, including beautifully updated baths with spacious walk-in showers. Two separate A/C systems help keep the home comfortable year-round. Generous living spaces and large bedrooms provide plenty of room to spread out. Outside, the acre-sized property and mature trees offer privacy and space that are increasingly hard to find. Add in an outstanding location with convenient access to shopping, dining, entertainment, and area attractions, and this home truly delivers. One-acre living, Butler Chain access, and a fantastic location—this is Florida living at its best.

9600 Ambleside Drive, Windermere

Listing courtesy of NATIONAL REAL ESTATE. 407-203-6903

$673,000

4 Beds ⋅ 3 Baths ⋅ O6430765 MLS

Beautiful 4 bedrooms, 2.5 bathrooms single-family home in the desirable Windermere area. This spacious home features a thoughtfully designed floor plan with the primary bedroom and en-suite bathroom conveniently located on the first floor, along with a dedicated office and laundry room. The main level also offers a formal dining room, a welcoming family room, and a well-appointed kitchen, creating an ideal space for everyday living and entertaining. Upstairs, you’ll find additional bedrooms offering privacy and flexibility for family or guests. Enjoy a comfortable outdoor space with a conservation area in the backyard and a convenient location close to shopping, dining, major highways, and nearby amenities. This home offers the perfect combination of comfort, functionality, and location. Schedule your showing today!

5421 Gemgold Court, Windermere

Listing courtesy of IRM INVEST., REAL EST.& MGMT.. 407-903-0134

$409,900

3 Beds ⋅ 3 Baths ⋅ O6433569 MLS ⋅ 8860 BLDG.

Priced to sell! Great location and highly desired community! This beautifully maintained two-level townhome in the charming Legado community of Windermere offers 1,578 sq. ft. of modern living space, featuring 3 bedrooms and 2.5 bathrooms. This home combines modern construction, energy efficiency, comfort, and convenience in one of Windermere’s sought-after locations. The kitchen features upgraded granite countertops, backsplash, 42" cabinets, stainless steel appliances, and an oversized island. The open-concept living area is perfect for entertaining and gathering with family and friends. The attached two-car garage provides additional convenience. Upstairs, you’ll find three comfortable bedrooms, including a spacious primary suite with a large private balcony offering beautiful views of the Magic Kingdom fireworks. The primary bedroom also features a spacious walk-in closet and an ensuite bathroom with dual sinks. The washer and dryer are conveniently located on the second floor. Ceiling fans with remote controls are installed in all bedrooms and the main living area. The highly desirable Legado community offers a peaceful setting surrounded by conservation areas and a relaxing pond, while providing excellent amenities including a community pool and playground. The property is currently tenant-occupied, with the lease having started in December 2024. This makes it an excellent opportunity for investors seeking an income-producing property in a highly desirable area. The location is unbeatable in Windermere, close to top-rated schools, shopping, dining, outdoor activities, and the Walt Disney World resorts and theme parks. Convenient access to 535, I-4, the Florida Turnpike, and 429, as well as nearby hospitals and major attractions. School zoning: Windermere High School, Horizon West Middle School, and Castleview Elementary School. Priced to sell! Don’t miss this opportunity to own a beautifully maintained townhome in one of Central Florida’s most desirable communities. Schedule your showing today!

8860 Herencia Alley, Windermere

Listing courtesy of WRA BUSINESS & REAL ESTATE. 407-512-1008

$1,500,000

5 Beds ⋅ 4 Baths ⋅ O6433513 MLS

An exceptional residence where refined design and effortless living converge. Meticulously remodeled throughout, the home welcomes you with bespoke modern woodwork gracing the foyer, living room, bedrooms, and loft — a testament to artisan-level craftsmanship rarely found at any price point. The loft has been reimagined as a private cinema, complete with a high-resolution projector, integrated ceiling speaker system, and commanding 120-inch screen, delivering a true theater experience within the comfort of home. Beyond the interiors, the residence reveals its most captivating feature: an infinity-edge pool that appears to dissolve into the tranquil lake beyond, framed each evening by the Disney Magic Kingdom fireworks illuminating the horizon — a nightly spectacle reserved for a fortunate few. Offered FULLY FURNISHED with curated modern pieces, the home transitions seamlessly to its next owner. A three-car garage, perimeter security camera system, and smart lock entry complete the offering, balancing sophistication with modern convenience. A rare opportunity to acquire a turnkey residence of this caliber — private showings available by appointment.

17526 Black Rail Street, Windermere

Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO. 407-622-2122

$1,870,000

6 Beds ⋅ 7 Baths ⋅ O6432932 MLS

Welcome to lakefront living in Windermere! Set along the shores of Lake Burden, this impressive 6-bedroom, 6.5-bath home offers more than 5,100 square feet of living space, a 3-car garage, and a flexible layout designed for both everyday living and entertaining. Featuring the builder’s major upgrades and owned by just one owner since purchased directly from the builder, this home has been exceptionally well maintained. Inside, soaring ceilings and generous living spaces create an immediate sense of openness, while expansive sliding doors bring the beautiful lake views right into the heart of the home. The spacious kitchen is ready for everything from quiet family dinners to a full house of guests. With two primary suites — one downstairs and one upstairs — plus an additional first-floor bedroom, the floor plan offers great flexibility for guests, multigenerational living, or a home office setup. Upstairs, oversized bedrooms, a large bonus room, and private balconies provide even more room to spread out and enjoy the views. The outdoor space is just as special, featuring an extended covered lanai, outdoor kitchen, mature landscaping, and a peaceful lakefront backdrop. Morning coffee by the water, weekend barbecues, sunset dinners — this home was made for Florida living. Located in Lake Burden South, in the heart of Windermere, this home offers a peaceful residential setting with convenient access to shopping, dining, entertainment, and everything the area has to offer. Big home, beautiful setting, fantastic layout — and a lake view that never gets old. Come see this one in person!

7467 Lake Albert Drive, Windermere

Listing courtesy of NOVA REAL ESTATE SERVICES INC. 407-592-1744

$1,945,000

6 Beds ⋅ 6 Baths ⋅ O6432910 MLS

Welcome to 4282 McKinnon Rd, a beautifully updated Windermere estate offering exceptional space, privacy, and flexibility on approximately 1.15 acres—with NO HOA. Featuring 6 bedrooms, 6 baths, nearly 5,900 square feet of living space, a private pool, and 3-car garage, this custom home combines an impressive floor plan with extensive recent improvements. Move-in ready and refreshed inside and out, the home features new windows and doors, new interior and exterior paint, new flooring, new AC systems, a new water heater, and a beautifully renovated pool. The thoughtfully designed floor plan is a standout, beginning with a spacious first-floor primary suite offering privacy and convenience. Also on the main level is a separate guest suite, ideal for visitors or multigenerational living, along with a private dedicated office for working from home. Generous living and entertaining spaces are filled with natural light, while the spacious kitchen offers abundant cabinetry, a center island, walk-in pantry, breakfast bar, and casual dining area. Upstairs, a junior primary suite with a private balcony creates another inviting retreat. Additional bedrooms provide plenty of room for family and guests, while the large bonus room over the garage offers endless possibilities as a home theater, game room, fitness studio, playroom, or additional living space. Step outside to enjoy the Florida lifestyle from the covered lanai and renovated private pool, surrounded by an expansive homesite and mature landscaping. With over an acre to enjoy and NO HOA, there is a rare sense of freedom, privacy, and breathing room. Offering extensive updates, multiple bedroom suites, a private office, oversized bonus room, pool, 3-car garage, over an acre of land, and NO HOA, 4282 McKinnon Rd delivers an exceptional combination of space and versatility in sought-after Windermere.

4282 Mckinnon Road, Windermere

Listing courtesy of COMPASS FLORIDA LLC. 407-203-9441

$5,500,000

6 Beds ⋅ 8 Baths ⋅ S5155388 MLS

Virtually Staged. Pre-Construction. To be built. This is where high-end living meets possibility. A lakefront estate currently under construction in Windermere, set on the shores of Lake Olivia with wide, unobstructed water views and rare privacy. This future residence will have 6 bedrooms, 6 full baths, and 2 half baths across 6,400+ sq ft, with 12’ ceilings on the main level, 10’ ceilings above, and expansive windows designed to frame the lake. Planned features include a gourmet kitchen with premium cabinetry and quartz surfaces, dual primary suites, private elevator, theater room, wet bar, and 4-car garage. Outdoor living will include a resort-style lanai, summer kitchen, custom pool and spa, and a private dock with direct lake access. Set on approximately 1.6+ acres in one of Windermere’s most desirable locations, this is a rare opportunity to secure a brand-new lakefront residence before completion.

1330 Lake Olivia, Windermere

Listing courtesy of EMPIRE NETWORK REALTY. 407-440-3798

$3,990,000

6 Beds ⋅ 7 Baths ⋅ O6430081 MLS

Welcome to this beautifully furnished luxury residence in the guard-gated community of Casabella in Windermere. Situated on a private half-acre homesite, this impressive Toll Brothers Villa Divina model offers approximately 6,881 square feet of thoughtfully designed living space featuring 6 bedrooms, and 7 full bathrooms. The home showcases elegant architectural details, soaring ceilings, abundant natural light, and expansive living areas designed for both everyday comfort and entertaining. The gourmet kitchen features premium appliances, custom cabinetry, an oversized island, generous workspace, and a seamless connection to the family room and dining areas. The first-floor primary suite provides a private retreat with a spa-inspired bathroom featuring dual vanities, a walk-in shower, and spacious closet areas. Additional bedrooms, a second-floor media room, loft, office, and flexible living spaces provide exceptional versatility. The outdoor living area features a private in-ground pool, covered lanai, and beautifully landscaped surroundings. Additional highlights include a three-car garage, tile roof, refined finishes, abundant storage, and carefully selected furnishings throughout. Offered fully furnished, this residence provides a seamless opportunity to enjoy Windermere living in one of Central Florida’s desirable gated communities. Conveniently located near premier shopping, dining, golf, entertainment, major roadways, and area attractions, this Casabella estate combines elegance, comfort, and convenience.

4201 Isabella Circle, Windermere

Listing courtesy of WRA BUSINESS & REAL ESTATE. 407-512-1008

$1,599,000

4 Beds ⋅ 2 Baths ⋅ S5155372 MLS

Virtually Staged. BOAT INCLUDED IN PURCHASE PRICE: Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity in the Town of Windermere. Boasting approximately 65 feet of private frontage and a dedicated boat dock, the property captures sweeping views across Wauseon Bay. The current home is in good condition and ready to move in. The interior showcases a refined yet comfortable cabin style with some modern flair and a open-concept layout, four bedrooms and thoughtfully updated living spaces. A beautifully appointed kitchen features custom cabinetry, quartz surfaces, and premium appliances, while restored hardwood flooring adds timeless character throughout. The primary suite opens to a private balcony overlooking the water, creating a serene retreat. Outdoors, the property offers a fenced yard and a rare combination of circular driveway and rear-access garage. Just moments from Windermere’s parks, tennis courts, farmers market, and private boat ramp, this home embodies the charm and lifestyle of lakefront living in one of Central Florida’s most desirable communities. There is an option to build a new home and boat dock, Permits have been approved to build a new modern home 3,500sf and 900sf covered boat dock with lift. This option would be $3.9MM

212 W 1st Avenue, Windermere

Listing courtesy of HOME WISE REALTY GROUP, INC.. 407-712-2000

$485,000

4 Beds ⋅ 3 Baths ⋅ O6432258 MLS ⋅ 7668 BLDG.

Welcome to this beautifully maintained 4-bedroom townhouse in the desirable area of Windermere FL. The home is offering the perfect blend of comfort, style, and scenic surroundings. With a spacious four-bedroom layout, this home provides plenty of room for everyday living, entertaining, and creating flexible spaces to suit your needs. Your master bedroom is situated on the first floor and upstarts you'll have an additional loft space. Enjoy the beautiful lake view from your porch that adds a peaceful and inviting entry to the home. Tasteful newer upgrades throughout include newer LVP flooring throughout the first floor and staircase, fresh paint, refinished kitchen cabinets, new toilets, new washer, complemented by upgraded fixtures and finishes that give the property a clean, modern feel. Whether you're looking for a spacious primary residence, a comfortable family vacation home, or an opportunity to enjoy the sought-after Windermere lifestyle, this townhouse is a wonderful opportunity. Don't miss the chance to make this inviting property your new home!

7668 Fairgrove Avenue, Windermere

Listing courtesy of VESTI LLC. 407-749-5489

$1,740,000

4 Beds ⋅ 4 Baths ⋅ O6431500 MLS

Perfectly positioned on the 8th fairway of the renowned Golden Bear Golf Course in Keene's Pointe, this stunning Victorian estate offers timeless elegance, exceptional craftsmanship, and breathtaking golf course views. A grand foyer welcomes you with an impressive circular staircase, setting the stage for the home's sophisticated design and gracious living spaces. The gourmet kitchen is a chef's dream, featuring a large center island, breakfast bar, premium finishes, and seamless flow into the main living areas, where a cozy wood-burning fireplace creates a warm and inviting atmosphere. A wraparound covered front porch adds classic Southern charm and provides the perfect place to relax and unwind. Designed for effortless indoor-outdoor living, the spectacular backyard is an entertainer's paradise. Enjoy a sparkling saltwater pool, gas-heated spa, newly installed outdoor kitchen, and a retractable screened lanai—all overlooking the picturesque fairways of the Golden Bear Golf Course. Located within the highly sought-after gated community of Keene's Pointe, residents enjoy 24-hour guarded security, an award-winning golf course, tennis courts, a resort-style community pool, and an exceptional lifestyle in one of Central Florida's premier neighborhoods. This extraordinary residence offers the perfect blend of luxury, comfort, and breathtaking surroundings.

8241 Tibet Butler Drive, Windermere

Listing courtesy of GOLFPARK PROPERTIES. 407-566-9482

$6,900,000

5 Beds ⋅ 6 Baths ⋅ O6430931 MLS

Stately and elegant lakefront estate showcasing the best of Isleworth West. This grand home spans more than 7,000 square feet with 5 bedrooms- of which, four are on the ground floor – plus office, gym, library, storage room, upstairs media room and downstairs bonus room, perched along Lake Louise, the only lake on the Butler Chain surrounded by Isleworth. Expansive formal and living spaces are highlighted by picturesque lake views. The seamless flow from room to room takes full advantage of a layout built for living. The chef’s kitchen with island, gas cooktop, stainless appliances, hidden walk-in pantry, and built-in hutch offer an abundance of space for entertaining or family gatherings. The primary retreat offers an escape from the ordinary with peaceful lake views, a master bath with jetted tub, garden and water view shower, and a showstopping two-story custom closet that will be the envy of all. The executive office with wood walls and built-in shelving offers a luxurious setting for attending to business from home. Three secondary bedrooms on the main floor are all spacious and feature ensuite bathrooms. Upstairs is a fourth bedroom, gym, library, and open media room with balcony. Outdoor amenities include a screened patio with summer kitchen, oversized resort-style pool with travertine decking, large green space, and private dock with covered boat lift plus dock-mounted jet-ski lifts, and 3-car garage. Home also includes a full-house generator. This coveted location within Isleworth West offers an intimate setting with a limited number of homesites and no pass-through traffic. Community is regarded as Central Florida’s most exclusive address with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional membership opportunities.

6055 Louise Cove Drive, Windermere

Listing courtesy of STOCKWORTH REALTY GROUP. 407-909-5900

$525,000

3 Beds ⋅ 2 Baths ⋅ A4702367 MLS

Welcome to this beautiful maintained traditional-style home in the highly desirable Town of Windermere, Florida, just minutes from the renewed Butler-Chain of Lakes. Nestled in a quiet, peaceful neighborhood, this 3-bedroom, 2-bathroom home offers 1,926 square feet of comfortable living space with thoughtful upgrades throughout. The updated kitchen features renovated cabinetry, while both bathrooms have been tastefully upgraded. The spacious primary suite includes a large walk-in closet, and elegant crown molding adds character to the primary bedroom and dining area. Additional highlights include the roof installed four years ago, beautiful tile flooring throughout the home with carpet in the living room and bedrooms, stylish glass shower doors in the secondary bathroom, and an attached two-car garage. Every detail reflects the pride of ownership and care this home has received over the years. Residents also enjoy access to fantastic community amenities, including a swimming pool, tennis courts, and a basketball court, providing opportunities for recreation just steps from home. This is a peaceful retreat with the opportunity to enjoy the sought-after Windermere style. This home is a beautiful place to call your own.

6679 Duncaster Street, Windermere

Listing courtesy of FLATFEE.COM. 954-965-3990

$675,000

5 Beds ⋅ 5 Baths ⋅ O6429931 MLS

Gorgeous former model home situated on an oversized corner lot with a beautiful private swimming pool! Designed for comfortable living and entertaining, this spacious home offers an exceptional layout and a highly desirable location near Walt Disney World, shopping, dining, and everyday conveniences. Fresh interior and exterior paint gives the home a clean, refreshed feel. The first floor features a generously sized primary bedroom with an en-suite bathroom. The open-concept kitchen overlooks the expansive family room, creating the perfect setting for relaxing afternoons, family gatherings, and entertaining guests. Upstairs, you will find a spacious bonus room with beautiful views, a large full bathroom, two additional bedrooms, and a conveniently located laundry room with the washer and dryer included. Step outside to enjoy the impressive pool and patio area, ideal for entertaining or embracing the Florida lifestyle. The separate detached building offers a garage on the first floor and a private bedroom with a full bathroom above. This versatile space is perfect for a guest suite, home office, studio, or additional living area. A truly special home offering abundant space, flexibility, and an outstanding location with convenient access to Central Florida’s world-famous attractions!

7236 Penkridge Lane, Windermere

Listing courtesy of ATLAS BLUE REALTY INC. 321-948-2242

$3,500,000

4 Beds ⋅ 6 Baths ⋅ O6430755 MLS

Welcome to the exclusive gates of Isleworth, golf front estate offers over 7,600 square feet of refined luxury living overlooking the fairway of the renowned Isleworth Golf & Country Club, one of the worlds most prestigious golf club communities, this championship course was designed by Arnold Palmer and set along the Butler Chain of Lakes. The neighborhood is defined by beautifully landscaped scenery, sweeping water views, and exceptional 24 hour guard gated privacy. This estate offers exceptional potential supporting four beds, six baths, a private office, inside gym, approached by a private driveway with ample guest parking and a 4 car garage. The two story residence opens with a regal marble foyer and fountain feature. Inside, vaulted ceilings, skylights, and wall to wall sliding glass doors fill the main living areas with natural light while framing views of the pool, sauna, golf views and rolling fairways beyond. A grand fireplace and wet bar create an inviting space for entertaining. The chef’s kitchen centers on a dramatic island and is highlighted by a striking copper range hood, warm cabinetry, and an open eat in layout designed for both everyday living and hosting. Above the garage, a private accessory dwelling unit provides flexible secondary living space or maids living. Each of the spacious bedrooms offers its own view and is finished with marble baths. A dedicated home gym adds further convenience. Exceptional amenities and sophisticated living in the world renowned community of Isleworth.

5524 Worsham Court, Windermere

Listing courtesy of ATLIS REALTY GROUP LLC. 863-212-5455

$3,400,000

6 Beds ⋅ 7 Baths ⋅ S5154885 MLS

Spectacular Private Gated Lakefront Estate on Lake Olivia in Windermere, with Multi Generational Living - From the moment you enter through the custom iron gates, you are welcomed into a private lakefront estate unlike any other. Nestled on 1.75 acres along the shores of Lake Olivia, this custom-built Mediterranean residence showcases Tuscan-inspired architecture, mature landscaping, and a winding paver drive creating a true sense of arrival and privacy. Offering six bedrooms, all with ensuite bathrooms, including a private attached one-bed mother-in-law suite with a private side entrance, this estate features an ideal floor plan with nearly all living space conveniently located on the main level, with the sixth bedroom and bonus/media room upstairs. Elegant craftsmanship is showcased throughout with stone accents, travertine and granite finishes, and refined details. The primary retreat features French doors opening to the screened lanai with pool and lake views, dual custom closets, and a luxurious bath complete with stone flooring, tiled shower, jetted tub with fireplace and mounted TV, dual vanities, private water closet with bidet, and illuminated makeup area. The attached one-bed apartment offers a private side entrance, full kitchen, living area and ensuite bedroom, perfect for guests or multigenerational living. The gourmet chef’s dream kitchen features double islands, granite countertops, premium appliances, including a full-size professional Wolf 6-burner and griddle gas range with double ovens, 48” Sub-Zero Pro refrigerator/freezer with lit glass door, food warmer drawer, additional convection oven, wine fridge, and butler’s pantry. Additional highlights include a separate media/games room upstairs, formal living and dining spaces, a spacious laundry room with pantry storage, and an oversized 3-car garage with keypad entry, side entrance, and epoxy flooring. The expansive 1,200+ square-foot screened lanai spans the rear of the home and is fully protected with 8 remote hurricane shutters. Enjoy multiple gathering areas overlooking the pool and lake, a summer kitchen with Viking grill, hood, fridge, and sink, stone fireplace, teak ceilings, and a breathtaking lagoon-style saltwater pool with a heart-shaped spa. Recent enhancements totaling over $200,000 include all-new light fixtures and ceiling fans, a whole-house generator with automatic transfer capability restoring power in under 15 seconds during an outage, Leaf Guard gutter system, new AC system, remote hurricane shutters, roof tile servicing and sealing for pest protection, newly installed side pavers, and fresh interior paint. Take in the stunning lake views from the oversized boathouse and screened dock room, featuring a motorized boat lift with direct access to Lake Olivia — a private spring-fed lake with no public access, sandy bottom, and exceptional opportunities for boating, skiing, and fishing. A rare opportunity to own a private lakefront estate with no HOA, multi-generational attached apartment, modern upgrades, and the tranquility of one of Central Florida’s most desirable private lakes. Conveniently located near world-class shopping, major highways, and area attractions. Move-in ready and available for immediate showings with a 360 Tour and floorplan available.

9679 Westover Roberts Rd, Windermere

Listing courtesy of TONYDAVIDSHOMES.COM, LLC. 321-559-1145

$400,000

3 Beds ⋅ 3 Baths ⋅ O6430630 MLS ⋅ Na BLDG.

Under contract-accepting backup offers. Accepting Back Up Offers!!!!!!! ABSOLUTELY STUNNING WINDERMERE END-UNIT TOWNHOME! Welcome home to this exceptional end-unit townhome, perfectly positioned in one of the most desirable locations within the community. Nestled against tranquil wooded conservation and lush green space, this home offers a rare sense of privacy with no front neighbors and direct access to a scenic community walking path. One of the largest floor plans in the neighborhood, this beautifully maintained 3-bedroom, 2.5-bath residence is filled with natural light, creating a bright, open, and inviting atmosphere throughout. The spacious open-concept kitchen, dining, and living area is ideal for both everyday living and entertaining. The kitchen is tastefully upgraded with granite countertops, a stylish tile backsplash, rich wood cabinetry, and quality flooring. Best of all, there is no carpet anywhere in the home! All kitchen and laundry appliances are included, making this home truly move-in ready. The thoughtfully designed floor plan provides each bedroom with convenient access to a bathroom. The generous primary suite features dual vanities, a large walk-in closet, and a spacious ensuite bath designed for comfort and functionality. Step outside to enjoy the private fenced courtyard leading to the oversized rear-entry two-car garage with a pedestrian door, offering both convenience and privacy. Enjoy low-maintenance living with an HOA that covers exterior maintenance, landscaping, roof maintenance, pest control, and access to the beautiful resort-style community pool and clubhouse. Located in the heart of Windermere, this home offers an unbeatable location with top-rated A schools and easy access to Disney, Lakeside Village, Horizon West, Winter Garden Village, shopping, dining, and major roadways. This is a rare opportunity to own one of the finest townhomes to come on the market in quite some time. Don't miss your chance to make this exceptional home yours!

12303 Langstaff Drive, Windermere

Listing courtesy of REAL BROKER, LLC. 855-450-0442

Windermere Florida Homes for Sale

Windermere Florida Homes for Sale