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$759,000
4 Beds 4 Baths O6437963 MLS
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, French drains, 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, stainless steel appliances, and a Bosch dishwasher, with 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, and direct access to the pool and patio. 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

$1,399,900
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

$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. 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

$710,999
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

$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

$1,187,000
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

$529,000
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
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 with EV Charger. 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

$3,700,000
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

$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 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

$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
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

$1,755,000
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

$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

$890,000
6 Beds 4 Baths O6435099 MLS
Watch Disney firework everyday from front porch. NO Carpet in the house. Stunning house in Windermere Isle in Gas community, Fully Fenced, Engineer wood floor and porcelain tile in bathrooms. Recent Upgraded kitchen and bathrooms cabinets and countertops and first floor luxury Engineer wood floor. Two downstairs bedrooms are perfect for a guest bedroom and a home office. Tankless gas water heater. Ceiling fan with remote control in all rooms. Crown molding, Chef kitchen, backsplash, stainless steel appliances with gas stove, walk-in pantry and Office Nook area. The huge Loft gives you an extra space for a secondary living area. The MASTER SUITE has a large double walk-in closet. Unwind from the day in your GARDEN BATH with soaking tub and semi-frameless glass shower with double shower head with rain showerhead. Another 2 bedrooms have jack and jill bathroom to share, Second floor laundry room with sink. Screen lanai with ceiling fan for enjoying outdoor living. Epoxy garage floor paint. Windermere Isle offers residents a Community Pool, Cabana and Playground. HOA fee includes full lawn services and 1 GIG Spectrum internet and cable with 4-5 streaming choices. Top rated school, Located close to 429, Disney and Hamlin Shops. Backyard is large enough to build your private dream pool.

8278 Procida Isle Lane, Windermere

Listing courtesy of AGENT GROUP REALTY. 561-565-5215

$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

$2,395,000
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

$999,000
6 Beds 5 Baths O6433721 MLS
Flexible living takes center stage in this 4,563-square-foot Windermere Trails home, where six bedrooms, four-and-a-half baths, multiple gathering spaces, and a substantial screened outdoor area create room for everyday life to unfold comfortably. The kitchen anchors the main living area with white cabinetry, a tiled backsplash, stainless-finish appliances, double wall ovens, and a large island with seating, keeping meal preparation connected to the surrounding living and dining spaces. A separate dining room and additional front room add even more flexibility downstairs, while upstairs, the expansive loft functions as a true second living area with plenty of room for recreation, hobbies, a workspace, or additional lounging space. The primary suite includes an en suite bath with dual sinks, a separate tub, and a glass-enclosed shower, while five additional bedrooms and multiple baths provide a layout with plenty of options throughout the home. One of the property’s most memorable spaces is the large screened and covered lanai stretching across the rear of the home, creating a shaded extension of the interior living areas and opening to the fenced backyard beyond. Set on a 10,400-square-foot lot in Windermere Trails, the home also offers access to visible neighborhood amenities including a community pool, playground, and covered pavilion. With generous interior square footage, adaptable living spaces, and a strong indoor-outdoor connection, this home offers a layout designed to accommodate a wide range of everyday needs.

8701 Iron Mountain Trail, Windermere

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

$559,000
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

$1,249,000
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

$510,000
4 Beds 3 Baths O6429767 MLS
Your dream home in Windermere is waiting for you! This beautiful home features 4 bedrooms, 2.5 bathrooms, and a 2-car garage, offering the perfect combination of comfort and style. The spacious kitchen is equipped with granite countertops, complemented by matching granite in all bathrooms. The first floor features durable tile flooring throughout, creating a bright, open, and easy-to-maintain living space. Located in the desirable Vineyard Square community, residents enjoy fantastic amenities, including a community swimming pool, cabana, tot lot, and passive park. The neighborhood is ideally situated near Central Florida's world-famous attractions, shopping, dining, major highways, and charming Downtown Windermere. Just minutes away, you'll find Winter Garden Village, known for its exceptional shopping, restaurants, outdoor events, and seasonal festivals. Outdoor enthusiasts will also appreciate the nearby Tibet-Butler Preserve, offering scenic walking and biking trails. Don't miss this incredible opportunity to own a home in one of Central Florida's most sought-after locations. Schedule your private showing today!

13831 Farella Alley, Windermere

Listing courtesy of TALENT REALTY SOLUTIONS. 407-910-2020

$682,000
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

$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

$1,995,000
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

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