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$475,000
3 Beds ⋅ 3 Baths ⋅ S5154426 MLS ⋅ Na BLDG.
Welcome to this charming two-story townhome in the highly desirable Windermere Trails community! Featuring 3 bedrooms, 2.5 bathrooms, and 1,631 sq. ft. of comfortable living space, this home offers an open-concept main floor seamless for daily living and entertaining. The kitchen is appointed with granite countertops, stainless steel appliances, a breakfast bar, and a spacious pantry. Upstairs, you will find all bedrooms, including a private owner's suite complete with an an-suite bathroom and generous closet space. Enjoy outdoor living with your private enclosed courtyard connecting the home to the detached 2-car garage. Community amenities include a resort-style pool, splash pad, dog park, playground, and scenic walking trails. Superb location with top-rated Orange County schools nearby and easy access to Disney, Horizon West dining, and major expressways. Schedule your private showing today!

8386 Iron Mountain Trail, Windermere

Listing courtesy of MY REALTY GROUP, LLC.. 786-847-7421
$579,000
3 Beds ⋅ 2 Baths ⋅ O6427997 MLS
Virtually Staged. Discover this beautifully maintained 3-bedroom, 2-bath corner-lot home in Windermere. Surrounded by tree-lined streets and a welcoming neighborhood atmosphere, this home combines timeless charm with everyday convenience. Enjoy relaxing on the covered front porch, perfect for morning coffee, visiting with the neighbors or unwinding after a long day. Inside, the thoughtfully designed floor plan offers comfortable living spaces that are ideal for both everyday life and entertaining. The home features a galley style kitchen positioned between a cozy breakfast nook and the dining room, allowing for both casual and traditional dining options. The split-bedrooms provide added privacy. The on-suite primary bathroom features a soaking tub, dual vanities and a separate stand alone shower. The shower glass and tile were replaced in the fall of 2025. The home features real bamboo hardwood flooring in all interior areas except the kitchen, nook, bathrooms and laundry room. From the living room, open the sliders and step into your oversized patio. This patio has a generous covered area and a screened portion, allowing you to comfortably enjoy outdoor living while being protected from the Florida sun, weather and insects. The fully vinyl fenced backyard has two access gates and is ideal for pets, play or outdoor gatherings. New gutters and water heater were added in 2026, offering added peace of mind. Residents of this community enjoy access to a resort-style pool, basketball court, tennis/pickleball courts and a walking path, offering endless opportunities for recreation, relaxation and an active lifestyle. Whether you are searching for your first home, looking to downsize, or simply wanting to enjoy the charm and lifestyle that Windermere is known for, this property offers an exceptional opportunity in a highly sought-after location. Conveniently located near excellent schools, shopping, dining, theme parks and major roadways, this home offers easy access to everything Central Florida has to share. Don’t miss this opportunity - schedule your showing today.

13231 Roxboro Road, Windermere

Listing courtesy of LA ROSA REALTY KISSIMMEE. 407-930-3530
$7,500,000
6 Beds ⋅ 8 Baths ⋅ O6426995 MLS
Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional craftsmanship, and resort-style amenities come together in one of Windermere's most coveted locations. Built in 2024 and spanning approximately 6,900 square feet under air (10,400 total square feet), this custom residence sits on a rare one-acre homesite along the iconic, paved Second Avenue, renowned for its festive holiday displays, spectacular sunsets, and unmatched charm. Designed for both everyday luxury and grand scale entertaining, this 6 bedroom, 7.5 bathroom home offers en-suite bedrooms with walk-in closets, including a private first floor guest suite. The stunning primary retreat features a spa inspired bathroom and a private balcony overlooking the lake, creating the perfect setting to enjoy breathtaking sunsets and nightly Disney fireworks. The heart of the home is a designer chef's kitchen featuring exquisite Cristallo countertops, premium Miele appliances, and seamless flow into the expansive living and entertaining spaces. A dramatic floating wood staircase with a striking stone accent wall serves as an architectural centerpiece, while an elevator provides effortless access to every level. Additional highlights include a custom onyx sink in the powder bath, elegant 8-foot solid wood core doors throughout, motorized blinds, and laundry rooms on both the first and second floors. Step outside to experience a true private resort. The heated infinity edge saltwater pool features a unique acrylic glass viewing wall, allowing swimmers to enjoy underwater lake views unlike anything else. The expansive summer kitchen is equipped with two oversized Big Green Egg grills, a hibachi grill, and generous entertaining areas perfect for hosting unforgettable gatherings. A spacious game room with a full bar, dedicated fitness room, and professionally designed dog run complete the home's exceptional lifestyle offerings. Boating enthusiasts will appreciate the impressive two story private dock with multiple lifts, providing direct access to the famed Butler Chain of Lakes. Car collectors will love the oversized four car garage with an automotive lift, an additional golf cart garage, and an exceptionally long driveway offering abundant guest parking, a rare luxury on Second Avenue. Constructed with impact-rated windows and doors, spray foam insulation, and energy-efficient systems, this home was thoughtfully built to provide superior comfort, security, and efficiency. Combining impeccable design, world-class amenities, spectacular waterfront views, and one of the finest addresses in Central Florida, this remarkable Lake Butler estate represents a rare opportunity to own a nearly new custom home in one of Windermere's most sought after neighborhoods. Be sure to click on the virtual tour links.

724 W 2nd Avenue, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396
$2,800,000
6 Beds ⋅ 8 Baths ⋅ W7887812 MLS
Exceptional custom estate in the exclusive guard-gated community of Bellaria featuring 6 bedrooms, 7 full bathrooms, 1 half bath, and a floor plan designed for both everyday living and entertaining. Positioned with pond views and no front neighbors, this residence has been recently painted inside and out and offers quality craftsmanship throughout. The main living areas showcase travertine flooring, while the gourmet kitchen is appointed with custom Bosby cabinetry, stone countertops, a paneled built-in refrigerator that blends seamlessly with the cabinetry and an oversized walk-in pantry with direct access to the interior laundry room. The custom Bosby cabinetry continues into the family room, creating a cohesive, high-end design. The thoughtfully designed layout provides exceptional privacy, with no bedrooms sharing a common wall. The spacious primary suite is located on the first floor fqacing the pool/backyard with a spaccious walk-in closet, upstairs you'll find 2 bedrooms and a dedicated movie theater, with the theater seating conveying with the sale. The outdoor living space is designed for year-round enjoyment, featuring a resort-style pool, covered lanai, summer kitchen, and a bedroom overlooking the pool, ideal for guests or multigenerational living. Mature privacy hedges surround the backyard, creating a secluded outdoor setting. Located just minutes from Winter Garden Village, major highways, top-rated schools, restaurants, shopping, and Orlando's world-class attractions, this exceptional home offers luxury, privacy, and convenience in one of Windermere's most desirable communities.

13250 Bellaria Circle, Windermere

Listing courtesy of CHARLES RUTENBERG REALTY INC. 866-580-6402
$629,900
5 Beds ⋅ 4 Baths ⋅ O6426386 MLS ⋅ Milano BLDG.
Virtually Staged. Welcome home to 11773 Bella Milano Ct — a 5-bedroom, 3.5-bath residence on a quiet cul-de-sac in the sought-after gated community of Belmere Village. Enjoy rare privacy with a wooded conservation view at the rear, bordering a park with no through-access, and a lot size just under a quarter acre. Inside, engineered hardwood and tile flooring flow through the main living areas (one living room is carpeted), beneath vaulted and 9'4"+ ceilings on the first floor. The spacious primary suite is a true retreat, featuring a garden tub, separate shower, dual vanities, private toilet closet, walk-in closet, and an adjoining sitting room with its own exterior entrance to the backyard. Four additional bedrooms deliver flexible space for family, guests, or a home office. The kitchen features stainless steel appliances. Major systems are well maintained: both HVAC units have been replaced (2023 and 2026), and the tile roof was resurfaced in 2023 with no major repairs since. A 2-car garage completes the home. Belmere's $130/month HOA includes a gated entrance, community pool, clubhouse, tennis courts, basketball court, sand volleyball court, playground, and fitness center — all within Windermere's top-rated school zone and minutes from the Butler Chain of Lakes and Winter Garden's Plant Street district.

11773 Bella Milano Court, Windermere

Listing courtesy of KELLER WILLIAMS ADVANTAGE 2 REALTY. murraycoleman@kw.com
$1,090,000
4 Beds ⋅ 4 Baths ⋅ O6425171 MLS
Virtually Staged. One or more photo(s) was virtually staged. *** BRAND NEW ROOF AUG 2026 *** This is your opportunity to own a home in Keene's Pointe, a 24-hour guard-gated golf community on the Butler Chain of Lakes and home to the Golden Bear Club. Built by David Weekley and proudly offered by its original owner, this 4-bedroom, 4-bathroom home offers 3,646 square feet of flexible living space, including a dedicated home office, a flex room, and a spacious upstairs bonus room that could serve as a potential fifth bedroom, media room, or game room. Upstairs is also equipped with a full bathroom. A tandem three-car garage provides room for multiple vehicles, a golf cart, additional storage, or a workshop area. Inside, the thoughtfully designed floor plan begins with a formal dining room and dedicated home office just off the foyer. A secondary bedroom and full bathroom are conveniently located near the front of the home, while the open-concept family room and kitchen create the heart of the home. The kitchen features a center island, cabinetry, and countertop space. There is an existing electric range, but the community is connected to natural gas, offering the option to convert the existing electric range. Sliding glass doors open to the covered lanai and private backyard, extending the living space outdoors. The spacious first-floor primary suite offers plenty of room for a sitting area or reading nook. The primary bathroom features dual vanities, a walk-in shower, garden tub, and a spacious closet. Two additional bedrooms are privately situated on the opposite side of the home and are separated by a flex room, making it ideal as a study area, hobby space, or additional sitting room. A full bathroom with direct access to the covered lanai completes this wing of the home. Residents of Keene's Pointe enjoy private boardwalks to Lake Tibet of the Butler Chain of Lakes, community boat ramp to Lake Burden, four playgrounds, scenic green spaces, and neighborhood events. Optional membership to the Golden Bear Club offers championship golf course, tennis, a swimming pool, fitness center, dining, and an active social calendar. In order to utilize these amenities, a Golden Bear Club membership is needed. Conveniently located near Walt Disney World, shopping, dining, everyday conveniences and services, this home offers an opportunity to enjoy the lifestyle and amenities of Keene's Pointe. Disclosure: Artificial Intelligence has been utilized in public remarks and removal of some personal property.

8344 Bowden Way, Windermere

Listing courtesy of ALIGN REAL ESTATE LLC. 305-389-2922
$448,000
4 Beds ⋅ 3 Baths ⋅ O6421245 MLS ⋅ N/A BLDG.
Virtually Staged. Seller may consider buyer concessions if made in an offer ~ Enjoy the best of Windermere living in this beautifully maintained 4-bedroom, 2.5-bath townhome with a rear facing 2-car garage in the sought-after Lake Burden South community! Offering a spacious, LOW MAINTENANCE LIFESTYLE, this home combines an ideal SPLIT BEDROOM floor plan with timeless finishes and an unbeatable location just steps from shopping, dining, and everyday conveniences. A charming covered front entry, attractive landscaping, and durable concrete TILE ROOF create welcoming CURB APPEAL. Inside, TILE & WOOD LAMINATE FLOORING flow throughout the home, while the light-filled OPEN CONCEPT design makes everyday living and entertaining effortless. FRENCH DOORS extend the living space to a private COURTYARD PAVER PATIO, creating the perfect spot to unwind, grill, or gather with friends. The kitchen is designed to be both functional and inviting, featuring rich cabinetry, granite countertops, a tiled backsplash, STAINLESS STEEL APPLIANCES, pantry storage, and a breakfast bar that overlooks the living and dining areas. The highly desirable MAIN FLOOR PRIMARY SUITE offers privacy and convenience with a generous WALK-IN CLOSET and a well-appointed en-suite bath. Upstairs, a versatile LOFT provides the perfect flex space for a home office, media room, or play area, while three additional bedrooms, a full bath, and upstairs laundry offer plenty of room for family, guests, or hobbies. Residents of Lake Burden South enjoy a COMMUNITY POOL and one of Windermere's most convenient locations, with easy access to Winter Garden Vineland Road, the area's beautiful lakes, Downtown Windermere, Disney, Winter Garden, Restaurant Row, shopping, dining, and major roadways. Whether you are looking for a full-time residence, a seasonal getaway, or a smart investment in one of Central Florida's most desirable communities, this exceptional townhome is ready to impress. Call today to schedule your tour and fall in love with Brownstone Street!

11429 Brownstone Street, Windermere

Listing courtesy of WEMERT GROUP REALTY LLC. 407-214-3967
$330,000
2 Beds ⋅ 3 Baths ⋅ O6424774 MLS ⋅ 10430 BLDG.
Welcome to this beautifully maintained 2-bedroom, 2.5-bath townhome-style condominium nestled in the gated community of Oasis Cove at Lakeside Village in the heart of Windermere. Offering the perfect blend of comfort, style, and convenience, this move-in ready home features an open-concept floor plan with abundant natural light, creating an inviting space for both everyday living and entertaining. Residents of Oasis Cove enjoy resort-style amenities, including a community pool, fitness center, playground, clubhouse, and beautifully maintained grounds, all within a secure gated entrance. In addition to the resort-style amenities the association fees also include water, internet, cable, ground maintenance and exterior maintenance for all homes. Ideally located just minutes from Disney, Horizon West, Winter Garden Village, major highways, shopping, dining, and top-rated schools, this home offers easy access to everything Central Florida has to offer. Whether you're looking for your primary residence, a second home, or an investment opportunity, this exceptional property checks all the boxes. Don't miss your chance to own a beautiful home in one of Windermere's most desirable communities—schedule your private showing today! *New Roof + New HVAC!!*

14030 Sparkling Cove Lane Unit 603, Windermere

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
$2,500,000
6 Beds ⋅ 4 Baths ⋅ O6418226 MLS
MULTI-GENERATIONAL LUXURY LAKEFRONT LIVING. Welcome to 1629 Hempel Avenue, a private lakefront retreat set on more than one gated acre along Lake Olivia, an approximately 88-acre, spring-fed lake with private access. Located in the desirable Gotha/Windermere area, this exceptional property offers rare peace and privacy while remaining convenient to Southwest Orlando’s renowned theme parks, premier shopping, Downtown Orlando, Orlando International Airport, highly regarded schools, and the Florida Turnpike. Mature trees, lush gardens, and thoughtfully designed outdoor spaces create a setting that feels secluded, established, and distinctly Florida. An antique church door provides a memorable entrance, setting the tone for a residence that blends refined finishes, distinctive character, and comfortable everyday living. The main residence features four bedrooms, two full bathrooms, and an expansive open-concept living area designed for entertaining while showcasing beautiful lake views. The oversized great room offers multiple gathering spaces, including a billiards area, a large television and game-day space, a generous dining area, and an impressive chef-inspired kitchen. At the center of the kitchen is an abundant quartz-topped island offering extensive workspace, seating, and a natural gathering place where guests can connect while meals are prepared. High-end flooring throughout the main home includes polished ceramic tile, travertine, and solid wood, while newer energy-efficient windows and doors enhance comfort and efficiency. The primary suite is a magazine-worthy addition created as a private lakeside sanctuary. Cathedral ceilings, polished ceramic tile flooring, expansive lake views, and a flexible sitting or exercise area create an open and relaxing environment. Two oversized custom closets provide exceptional storage. The luxurious bathroom features floor-to-ceiling ceramic tile, quartz countertops, an oversized porcelain soaking tub, and a spacious walk-in shower room. Four distinctive outdoor living areas invite you to enjoy the property throughout the year. Gather around the fire in the stone-paver garden area, relax within the private walled courtyard surrounded by potted plants and the soothing sound of a water fountain, or spend the day along the expansive backyard and private boat dock. The recently updated infinity-edge pool and heated spa overlook the lake, creating a resort-style setting for relaxing, entertaining, and enjoying unforgettable sunsets. A separate guest residence adds tremendous flexibility and privacy. Complete with two bedrooms, two bathrooms, a kitchen, and a living area, it is ideal for multigenerational living, extended guests, or an on-site caretaker. A private gated driveway and abundant parking accommodate multiple vehicles with ease. Combining two complete residences, more than an acre of lakefront land, exceptional outdoor living, mature landscaping, and private access to Lake Olivia, this one-of-a-kind estate offers a lifestyle rarely available in Central Florida.

1629 Hempel Avenue, Windermere

Listing courtesy of COLDWELL BANKER REALTY. 407-352-1040
$629,900
4 Beds ⋅ 3 Baths ⋅ O6423949 MLS
Situated on a distinguished homesite in one of Windermere's most sought after locations, 13328 Overstreet Road impresses right when you pull into the oversized 6+ CAR PAVER DRIVWAY with parking for up to six vehicles. If any of those vehicles are electric, you can charge them using the installed TESLA CAR CHARGER and save $$ on the electric bill with the PAID-OFF SOLAR PANELS. This home defines exceptional value and modern efficiency. At the heart of the home, the GOURMET KITCHEN is an entertainer's dream, with not one, but two center islands, ample solid WOOD CABINETS with crown molding, granite counters, and a tile backsplash. A stainless steel appliance package complements these features. A spacious dining area, family room, a mini mudroom off the garage, and a multipurpose space with additional cabinetry perfect for a small office, coffee bar, or wine bar. If you are looking for some multigenerational space, take advantage of the downstairs ensuite, which includes built-in closet organizers, a new vanity and toilet and a walk in shower. There is no carpet; the entire first floor has ceramic tile and the stairs and upstairs feature newly installed hardwood flooring. Luxurious master suite provides ELECTRIC BLINDS to let the light in and out at your fingertips, a perfectly organized walk in closet with custom built ins plus a double sink vanity with vessel sinks, modern light framed mirrors and a remodeled huge walk in shower complete with a shower wand, RAINHEAD SHOWER  and pebble stone floor. The second floor also offers a tremendous bonus/game room, media lounge, office or fitness studio along with 2 additional bedrooms, a full bath, and a laundry room with its own built-in sink and cabinet. Additional interior upgrades include plantation shutters on the first floor, an electric blind to the exterior and a digital thermostat. Exterior features include a SCREEN ENCLOSED LANAI  overlooking the fully fenced backyard for quiet comfort, privacy and shade from the yard's mature landscaping. Pavers line the back patio, making it possible to step right outside to both grill and dine al fresco during the temperate fall, winter, and spring months here in Central Florida. Additional features include YEAR ROUND HOLIDAY LIGHTING installed on the home making you ready for every season with the flip of a switch. Neighborhood features include a community pool complete with lounge chairs and a covered pavilion, a basketball court, a tennis court, a putting green, playgrounds covered from the sun or rain, and plenty of green space. LOCATION BENEFITS include easy access to DISNEY, SR 429, SR 408 to Downtown Orlando, Florida Turnpike, I4, shopping, restaurants and much more! Combining sophisticated finishes, versatile living spaces, and cutting-edge energy-conscious upgrades, this exceptional Windermere residence offers a lifestyle as impressive as the home itself.

13328 Overstreet Road, Windermere

Listing courtesy of RE/MAX PRIME PROPERTIES. 407-347-4512
$798,000
5 Beds ⋅ 5 Baths ⋅ O6422241 MLS
Discover refined living in one of Windermere's most sought-after communities. This exceptional 5-bedroom, 5-bath residence in Summerport perfectly blends timeless elegance, everyday comfort, and an unmatched location. Offering an ideal floor plan for both everyday living and entertaining, this beautifully maintained home features a dedicated office, formal dining room, spacious living room, family room, and thoughtfully designed living spaces throughout. The entire first floor showcases upgraded luxury vinyl flooring, while the gourmet kitchen is appointed with beautiful granite countertops, stainless steel appliances, abundant cabinetry, and a breakfast bar with seating, perfect for casual dining and gathering with family and friends. Situated on an oversized homesite, the backyard has been thoughtfully upgraded to create the perfect outdoor retreat. Enjoy a spacious covered lanai, an extended paver patio, and a fire pit, offering the ideal setting for entertaining or relaxing under the shade of the mature Trees. Upstairs, you'll find all 5 generously sized bedrooms, each complemented by access to a full bathroom, providing exceptional comfort and privacy for family members and guests alike. The first floor features a spacious private office that can easily be converted into a media room or 6th bedroom, complemented by a full bathroom for added flexibility. A spacious 3-car garage offers abundant room for vehicles, storage, and recreational equipment. Designed with efficiency in mind, the home is equipped with solar panels producing approximately 22–23 MWh annually, delivering substantial energy savings while reducing utility costs. Summerport is one of Windermere's most desirable communities, offering residents an exceptional lifestyle with resort-style amenities, including a community pool, fitness center, tennis courts, sand volleyball courts, playgrounds, scenic walking trails, and beautiful lakes. Families will appreciate being zoned for highly rated schools, including the sought-after Windermere High School. Ideally located just minutes from Walt Disney World, Winter Garden Village, Publix, premier shopping, dining, and major highways, this home presents a rare opportunity to enjoy luxury living in one of Central Florida's most prestigious communities.

4642 River Gem Avenue, Windermere

Listing courtesy of JOHN SILVA REALTY & ASSOCIATES. 407-420-7908
$6,700,000
8 Beds ⋅ 10 Baths ⋅ O6422852 MLS
Virtually Staged. Welcome to an extraordinary new construction waterfront estate built by Element Home Builders, located in the prestigious 24-hour guard gated community of Keene’s Pointe. Situated on a private cul-de-sac, this one of a kind residence rests on a spectacular 0.78 acre homesite with 518 feet of combined waterfront overlooking a serene pond and the beautiful waters of Lake Burden. Offering 8,133 square feet under air and 10,971 total square feet, this exceptional home features 8 bedrooms, 7 full bathrooms, and 3 half bathrooms with unparalleled craftsmanship and luxury finishes throughout. A grand marble foyer welcomes you with soaring ceilings, designer lighting, wood beams, and rich solid oak flooring. The stunning chef’s kitchen features custom solid wood cabinetry, stunning countertops, Thermador paneled refrigerator and freezer with white wine refrigeration, Wolf range, built-in convection oven, microwave, and a custom exhaust hood. The expansive great room showcases a natural stone fireplace and wall to wall sliders that open to breathtaking views of the infinity edge saltwater pool, spa, backyard oasis, and Lake Burden. The luxurious primary suite offers panoramic water views, custom illuminated walk-in closets, a spa inspired bathroom with a massive shower, designer fixtures, and a freestanding soaking tub. Additional highlights include a temperature controlled wine cellar, hidden elevator, executive study with custom built-ins, five spacious main level bedrooms, and a spectacular second floor featuring a private gym with reinforced insulation, custom theater, loft with kitchenette, balcony overlooking the water, and three ensuite bedrooms. Outdoor living is designed for entertaining with your summer kitchen including a heavy duty grill and hood, motorized screens for the entire lanai, multiple gathering areas, fire pit, private putting green, and a nature path leading to your covered boat dock with boat lift for endless Lake Burden adventures on a 125 acre skiable lake. A four-car garage with built in ceiling lighting tracks and electric vehicle charging completes this exceptional residence. Keene’s Pointe offers an unmatched lifestyle with the Golden Bear Club, featuring a championship golf course, clubhouse, fitness center, tennis courts, resort-style pool, and numerous parks and recreation areas. Ideally located just minutes from Walt Disney World, world class dining, shopping, and top rated schools, with close proximity to Windermere Preparatory School. This rare never been lived in lakefront estate is being offered for the first time and represents a unique opportunity to own one of Central Florida’s finest custom homes. Be sure to click on the virtual tour links.

8342 Boyla Court, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396
$330,000
3 Beds ⋅ 2 Baths ⋅ O6420653 MLS ⋅ 11446 BLDG.
Welcome to 11446 Jasper Kay Terrace, Unit 103, a beautifully updated first-floor condominium offering comfortable, low-maintenance living in a gated Windermere community. This move-in ready residence features a desirable split-bedroom floor plan with three bedrooms and two bathrooms, providing both privacy and functionality.The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating an inviting space for everyday living and entertaining. Recent updates include new kitchen countertops, newer kitchen appliances, updated bathrooms, recently replaced flooring throughout the main living areas, and a new HVAC system installed in 2025, providing added comfort and peace of mind. Abundant natural light creates a bright and welcoming atmosphere.The spacious primary suite features a walk-in closet and an updated en-suite bathroom. Two additional bedrooms provide flexibility for guests, a home office, or other lifestyle needs. Step outside to the private screened and covered patio, the perfect place to enjoy your morning coffee or relax at the end of the day.Residents enjoy access to a variety of community amenities, including a resort-style swimming pool, clubhouse, fitness center, playground, volleyball court, BBQ and picnic areas, scenic walking trails, water service, and valet trash. One reserved parking space is included.The community has recently completed extensive exterior improvements, including new roofs, freshly resurfaced and striped parking areas, and exterior building repainting, enhancing both curb appeal and long-term value. Fiber optic internet service is also available for high-speed connectivity.Conveniently located just minutes from Walt Disney World, Winter Garden Village, major highways, and directly across from Lakeside Village Center, this home offers easy access to shopping, dining, entertainment, and top-rated schools. Whether you’re looking for a primary residence, seasonal retreat, or investment opportunity, this updated condo offers the perfect combination of modern improvements, community amenities, and an exceptional location.

11446 Jasper Kay Terrace Unit 103, Windermere

Listing courtesy of SOUTHERN REALTY GROUP LLC. 407-217-6480
$560,000
3 Beds ⋅ 2 Baths ⋅ O6420991 MLS
Welcome to this charming and inviting home nestled in the highly desirable Lake Sawyer South community in Windermere. As you drive through the neighborhood, you'll immediately appreciate the mature landscaping, beautiful tree-lined streets, and peaceful atmosphere that make this communityso special. Upon arrival, you're greeted by a spacious covered front porch — the perfect place to relax and enjoy the Florida lifestyle. Step inside to a welcoming, wide foyer that opens to a bright and airy living room featuring soaring ceilings and an abundance of natural light. Two secondary bedrooms are thoughtfully positioned at the front of the home, offering privacy and flexibility for family members, guests, or a home office. The formal dining room is enhanced by a large window that fills the space with beautiful natural light, creating an inviting setting for entertaining. The open-concept kitchen overlooks the living room, making it ideal for gathering with family and friends. It also includes a cozy breakfast nook, perfect for casual everyday meals. Privately located at the rear of the home, the spacious primary suite is filled with natural light from three large windows. The en-suite bathroom features dual vanities, a soaking tub, a separate walk-in shower, a walk-in closet, and an additional linen closet for extra storage. Sliding glass doors from the living room lead to a covered and screened lanai and a fenced backyard with a paved patio, providing the perfect space for outdoor dining, entertaining, or simply unwinding. Offering 1,706 square feet of living space, this well-maintained home features 3 bedrooms, 2 bathrooms, a formal dining room, an open living room, a functional kitchen, a dedicated laundry room, and a two-car garage. Conveniently located just minutes from Publix, coffee shops, dinners, restaurants, shopping, personal storage facilities, and schools. This home combines comfort, convenience, and an exceptional Windermere location. Don't miss the opportunity to make this beautiful and welcoming home your own—schedule your private showing today! The existing solar panel financing is transferable to qualified buyers, offering the opportunity to enjoy energy savings without the upfront installation cost.

13219 Charfield Street, Windermere

Listing courtesy of DENIZ REALTY PARTNERS LLC. 407-704-0780
$6,500,000
5 Beds ⋅ 7 Baths ⋅ O6420326 MLS
Virtually Staged. An exceptional new construction offering within The Gardens of Isleworth, this newly completed residence by premier custom homebuilder Goehring & Morgan presents a rare opportunity to enjoy the ease of modern luxury within one of the world's most distinguished golf club communities. Thoughtfully designed and never lived in, the home combines timeless architecture with professionally curated interiors by Design Specifications, creating a refined retreat where every detail has been carefully considered. Spanning more than 5,400 square feet, the five-bedroom residence unfolds through a series of light-filled living spaces distinguished by bespoke millwork, tailored cabinetry, and a sophisticated palette of designer-selected finishes. Clean architectural lines and expansive gathering areas create an atmosphere that feels both grand and inviting, while thoughtfully integrated design elements elevate everyday living. Throughout the home, custom cabinetry conceals a fully integrated Sub-Zero, Wolf, and Cove appliance suite, allowing the chef's kitchen to maintain its beautiful aesthetic while delivering professional-grade performance. Well-appointed entertaining spaces nearby transition effortlessly from intimate family gatherings to larger celebrations.Private bedroom retreats offer comfort and tranquility, while spa-inspired baths showcase carefully selected finishes, fixtures and materials that evoke exceptional craftsmanship. The primary suite serves as a sanctuary unto itself, complete with a private beverage bar and thoughtfully designed spaces that encourage both relaxation and retreat.Beyond the interiors, walls of glass open to an inviting outdoor environment designed for year-round enjoyment. A fully equipped summer kitchen anchors the outdoor living experience, creating a natural extension of the home's entertaining spaces and providing the perfect backdrop for gatherings beneath Florida's sunshine and tropical climate.Surrounded by lush landscaping, sparkling water features, and the natural beauty that defines The Gardens of Isleworth, the residence enjoys a setting that feels both private and refined. Residents of Isleworth enjoy access to a lifestyle renowned for championship golf, world-class amenities, exceptional service, and a level of privacy rarely found. Combining the freshness of brand-new construction with the prestige of an established luxury community, this is more than a home, it is an opportunity to experience Isleworth at its finest.

9316 Gladys Garden Ct, Windermere

Listing courtesy of ISLEWORTH REALTY LLC. 407-909-9000
$745,990
5 Beds ⋅ 3 Baths ⋅ O6420597 MLS
Welcome to one of the most desirable communities in Windermere! This beautifully designed home offers 5 spacious bedrooms, 3 full bathrooms, and an exceptional floor plan featuring a large family room on the main level and an additional loft upstairs, providing the perfect balance of comfort, functionality, and flexible living space. Boasting approximately 3,285 square feet of living area, this is one of the builder’s most popular and highly sought-after floor plans. Every room has been thoughtfully designed to maximize space, natural light, and everyday convenience, making it ideal for growing families, entertaining guests, or working from home. The community offers outstanding amenities and a welcoming neighborhood atmosphere. Residents enjoy convenient access to major highways, shopping centers, supermarkets, restaurants, and everyday essentials. Located in the heart of Central Florida, this home is just a short drive from Disney World, Universal Orlando Resort, SeaWorld Orlando, and many of the area’s world-famous attractions, while also providing easy access to Orlando International Airport and Downtown Orlando. If you’re looking for a spacious, move-in-ready home in one of Windermere’s most sought-after communities, this is an exceptional opportunity you won’t want to miss.

7409 Fairgrove Avenue, Windermere

Listing courtesy of SUNSTAR REALTY FL INC. 407-750-6100
$295,000
2 Beds ⋅ 2 Baths ⋅ O6420460 MLS ⋅ 3 BLDG.
Step inside this home from anywhere! To experience a fully immersive walk-through of this home click on the Video or Virtual Tour button on this page. Welcome to effortless Florida living in this move-in ready, light-filled first-floor condo located in the heart of Windermere. Perfectly positioned, this beautifully maintained residence offers the ideal combination of comfort, convenience, and resort-style amenities just minutes from Disney, Winter Garden Village, & directly across from Lakeside Village Center with shopping, dining, and everyday conveniences. Designed with a desirable split-bedroom floor plan, this spacious home features an inviting open-concept layout that seamlessly connects the kitchen, dining, and living areas, creating the perfect space for both entertaining and everyday living. Crown molding adds an elegant touch throughout, while abundant natural light enhances the warm, welcoming atmosphere. The spacious primary suite provides a peaceful retreat with a large walk-in closet and private en-suite bath. Two additional bedrooms offer flexibility for family, guests, or the perfect home office. Step outside to your private screened and covered patio, an ideal place to enjoy morning coffee or relax after a long day. Located within a beautifully maintained gated community, residents enjoy an exceptional collection of resort-style amenities, including a sparkling swimming pool, clubhouse, fitness center, playground, volleyball court, BBQ and picnic areas, scenic walking trails, plus water and valet trash service for added convenience. One reserved parking space is included. Adding even more value, the community has recently completed significant exterior improvements, including new roofs, freshly resurfaced and striped parking areas, and exterior building repainting, enhancing both curb appeal and long-term investment potential. Fiber optic internet is also available, providing high-speed connectivity for remote work, gaming, and streaming. Whether you’re searching for a primary residence, vacation home, or investment opportunity, this exceptional Windermere condo offers low-maintenance living, outstanding amenities, and an unbeatable location close to top-rated schools, major highways, world-class attractions, shopping, dining, and everything Central Florida has to offer.

8180 Boat Hook Loop Unit 102, Windermere

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
$2,450,000
4 Beds ⋅ 5 Baths ⋅ O6419164 MLS
Completely renovated in 2025. State-of-the-art showpiece located in the beautiful Estates at Lake Clarice. This updated residence offers an effortless blend of generous living spaces and serene surroundings with re-designed landscaping and updated landscape lighting on a 1-Acre Private Lot! From the moment you enter through the dramatic double 12' iron and glass doors the home makes a bold statement with clean architectural lines. Large format Taj Mahal tile, soaring ceilings and OPEN concept design that feels both impressive and inviting. Formal living and dining, kitchen with eat in breakfast nook and bar, office, four en-suite bedrooms, five full bathrooms and a media room-ALL ON ONE FLOOR! Stunning chef's kitchen appointed with new custom modern premium cabinetry, newly installed high end appliances, new monolithic quartz island featuring a waterfall edge cascading to the floor all seamlessly flows into the main living and dining area-ideal for both intimate gatherings and large scale entertaining. The family room offers a glass wall of expansive sliders which fully retract blurring the line between indoors and out, enhancing the homes bright airy ambiance. The oversized screened in lanai is a, fully enclosed outdoor living space designed for year round enjoyment. This impressive retreat features a spectacular pool, generous lounge and dining areas, an outdoor kitchen and a pool bath! The Primary Suite is a private sanctuary leading out to the pool deck, along with the Spa-like bath, complete with dual vanities, separate Zen inspired soaking tub, inviting shower with multiple shower heads and bench seating. Huge walk-in closet with built-ins, a bespoke 3 way panoramic dressing alcove featuring three full-length 8' mirrors. Thoughtfully designed throughout with substantial updates including newer roof, oversized gutters and three newer air conditioners (one newly installed in the single portico/breezeway garage. Perfect for gym, hobby room or music studio). Newer water heater, two high end smart fireplaces with remotes, custom drapes, plantation shutters, shiplap ceilings and walls, newer high end ceiling fans inside and out, new custom 7 1/2 inch base molding. Just too many upgrades to mention. A must see in Windermere. Ideally located just minutes to Windermere High School, Windermere Prep, downtown Windermere, downtown Winter Garden, Walt Disney World, Universal and the Mall of Millenia.

4205 Clarice Estates Drive, Windermere

Listing courtesy of DALTON WADE INC. 888-668-8283
$1,549,000
5 Beds ⋅ 4 Baths ⋅ O6417606 MLS
Back on market due to buyer non-performance. Exceptional value in Lake Butler Sound! Welcome to 11027 Hawkshead Court, a beautifully updated luxury home in Windermere, FL offering 4 bedrooms, a dedicated office, 4 bathrooms, approximately 3,500 square feet, and a private 0.4-acre corner lot within one of Central Florida's premier guard-gated communities with 24-hour roving security. Extensively renovated between 2022 and 2026, this move-in-ready pool home blends timeless design, quality craftsmanship, and high-end finishes throughout. The open-concept floor plan is anchored by a chef's kitchen featuring upgraded countertops, a 7-foot built-in Dacor refrigerator with dual ice makers, 5-burner Dacor gas cooktop, double wall ovens with steam cooking, and abundant prep and storage space. New flooring throughout creates a seamless flow, while 12-foot ceilings in the main living areas and primary suite enhance the home's spacious feel. Designed for both everyday living and entertaining, the home showcases custom built-ins with a rolling library ladder, a striking entertainment wall with fireplace and built-in lighting, and a thoughtfully designed split floor plan. A private office with custom built-in shelving offers the perfect work-from-home space. The spacious primary suite is privately positioned away from the secondary bedrooms and features dual California Closets and a spa-inspired bath with marble tile, a custom vanity, and a freestanding soaking tub. Two secondary bedrooms share a Jack-and-Jill bathroom, while the fourth bedroom has its own full bath, making it ideal for guests, teens, or multigenerational living. Step outside to your own private backyard retreat featuring a gas-heated pool and raised spa, multiple covered and open-air entertaining areas, a turfed putting green, and an additional fenced grassy side yard. Situated on a premium corner lot bordered by two quiet cul-de-sacs, the outdoor living spaces provide exceptional privacy and tranquility. Additional upgrades include premium Pella doors, interior and exterior paint, a whole-home owned water softener system, new flooring throughout, a new septic drain field, custom California Closet systems, and numerous additional improvements that make this home truly move-in ready. Located in the Reserve at Lake Butler Sound, this exceptional property offers luxury, privacy, and convenience just minutes from downtown Windermere, top-rated schools, world-class golf, fine dining, shopping, and Orlando's premier attractions. A rare opportunity to own a meticulously updated luxury home in one of Windermere's most sought-after communities.

11027 Hawkshead Court, Windermere

Listing courtesy of KENNEDY REALTY GROUP LLC. 407-590-6192
$435,000
3 Beds ⋅ 3 Baths ⋅ O6418023 MLS ⋅ 12988 BLDG.
Welcome to 12988 Borland Street in sought-after Wickham Park, where comfort, convenience, and low-maintenance living come together in the heart of Windermere. This beautifully maintained 3-bedroom, 2.5-bath townhome offers a bright, open floor plan designed for modern living. Natural light fills the spacious living and dining areas, highlighting the ceramic tile flooring throughout the main level. The well-appointed kitchen features stainless steel appliances, a center island, abundant counter space, a large pantry, and a casual dining area perfect for everyday meals and entertaining. A versatile flex space tucked behind privacy doors on the first floor provides endless possibilities as a home office, playroom, guest retreat, or hobby room. Upstairs, the spacious primary suite offers a peaceful retreat with a walk-in closet, double vanity, and private ensuite bath. Two additional generously sized bedrooms, an additional upstairs full bathroom, and ceiling fans throughout, provide comfort and flexibility for family and guests. New waterfall faucets have been installed in all bathrooms for a modern touch. Significant recent updates include a new roof (2024) and impact-resistant windows installed in April 2026, complete with a transferable lifetime warranty. Step outside to your private, low-maintenance backyard oasis featuring lush artificial turf, decorative stone accents, and vinyl privacy fencing—perfect for relaxing, entertaining, or letting pets play without the hassle of yard work. The HOA takes care of exterior maintenance, allowing you to enjoy a truly lock-and-leave lifestyle. Residents of Wickham Park enjoy exceptional community amenities including walking trails, ponds, parks, playgrounds, green spaces, a dog park, and a resort-style community pool. Located within a highly rated school district and just minutes from Publix, restaurants, fitness centers, world-class golf courses, Tibet-Butler Preserve, the Butler Chain of Lakes, Walt Disney World, and major highways including SR 429, SR 408, I-4, and the Florida Turnpike, this home offers unmatched access to everything Central Florida. Move-in ready and ideally located, this is Windermere living at its finest. Schedule your private showing today.

12988 Borland Street, Windermere

Listing courtesy of LOKATION. 954-545-5583
$1,550,000
6 Beds ⋅ 5 Baths ⋅ O6416690 MLS
BACK ON THE MARKET!! Previous buyer was unable to complete the purchase. Welcome to an exceptional residence in the prestlgious gated community of Oxford Moor, Windermere, where timeless elegance meets modern comfort. This impressive 6-bedroom, 4.5-bathroom estate offers over-the-top space for both refined living and effortless entertaining, complete with a spacious 3-car garage and an expansive, thoughtfully designed floor plan. From the moment you enter, you’ll appreciate the home’s grand scale, abundant natural light, and inviting living spaces designed to accommodate both intimate gatherings and large celebrations. The luxurious primary suite and generously sized secondary bedrooms provide comfort and privacy for family and guests alike. Step outside to your private resort-style oasis, featuring a beautifully redesigned pool and spa completely renovated in 2025, creating the perfect backdrop for relaxation and outdoor entertaining. Meticulously maintained and extensively updated, this home offers exceptional peace of mind with both HVAC systems replaced in 2020, fresh interior and exterior paint completed in 2022, a new water heater installed in 2023, and both the well pump and pool pump replaced in 2026. Perfectly positioned in one of Windermere’s most coveted communities, Oxford Moor offers a serene setting while remaining just minutes from top-rated schools, upscale shopping, fine dining, championship golf, major roadways, and Central Florida’s renowned attractions. A rare opportunity to own a beautifully updated luxury residence that seamlessly combines sophistication, comfort, and enduring value. Experience the lifestyle you deserve—schedule your private tour today.

5741 Oxford Moor Boulevard, Windermere

Listing courtesy of FLORIDA CONNEXION PROPERTIES. 407-574-2636
$11,750,000
6 Beds ⋅ 10 Baths ⋅ O6416194 MLS
Virtually Staged. A true Lake Butler trophy estate. Set within the world-famous gates of Isleworth and commanding panoramic western sunset water views of Lake Butler from virtually every room, 9832 Laurel Valley Drive offers over 11,000 square feet of luxury lakefront living, situated upon 150 feet of expanded sandy beachfront, thoughtfully enlarged by the current owners, in one of Florida’s most well known communities. This statement home features six bedrooms, seven full bathrooms, and three half bathrooms, a newly installed bespoke theater room with custom seating, an infrared sauna and dedicated wellness and fitness area, two full bars, a private pub and game room, an elegant pool and spa, a fully equipped summer kitchen, and multiple levels of outdoor living and lounge space overlooking the lake. Complemented by countless additional spaces designed for both grand-scale entertaining and everyday enjoyment, every room exudes elegance and has been meticulously designed and expertly executed down to the finest detail. Beyond its unmatched location and architecture, the home has benefited from several million dollars’ worth of enhancements and upgrades, further elevating an already impressive estate into something truly magnificent. The result is a residence that blends timeless luxury with modern comfort while offering one of the most desirable waterfront settings in Central Florida. Not all lakefront homes are created equal, and Laurel Valley is a shining example of that. More than a home, 9832 Laurel Valley Drive is a statement. A trophy estate befitting a legacy. A rare opportunity to own one of Florida’s most compelling waterfront properties ever. The home may be negotiated to include select furniture, a brand-new pontoon boat, two new Sea-Doo jet skis, and a golf cart.

9832 Laurel Valley Drive, Windermere

Listing courtesy of REAL BROKER, LLC. 407-922-8986
$2,800,000
4 Beds ⋅ 6 Baths ⋅ O6414325 MLS
Set on an elevated corner homesite within Isleworth, this four-bedroom residence presents a unique opportunity to secure a coveted address in one of Central Florida's most distinguished private golf communities. Encompassing more than 4,700 square feet, the property offers exceptional potential for renovation, customization, or the creation of a new vision tailored to today's luxury lifestyle.Positioned overlooking the 6th tee of Isleworth's renowned championship golf course and across from a scenic pond with water features, the homesite enjoys a picturesque setting with golf and water views and mature landscaping. Existing amenities include a pool, summer kitchen, circular driveway, and a three-car garage.For buyers seeking an opportunity to personalize a home within Isleworth or establish a long-term presence in this exceptional community, few properties offer such a compelling combination of location, scale, and potential. Surrounded by the Butler Chain of Lakes and secured by four staffed guard gates, Isleworth is renowned for its championship golf, exceptional amenities, and unparalleled lifestyle, with club membership available separately.

5073 Latrobe Dr, Windermere

Listing courtesy of ISLEWORTH REALTY LLC. 407-909-9000
$10,200,000
6 Beds ⋅ 9 Baths ⋅ O6411906 MLS
An extraordinary brand-new contemporary lakefront estate on prestigious LAKE BUTLER, part of the renowned Butler Chain of Lakes, offering an exceptional blend of architectural sophistication, modern luxury, and unparalleled waterfront living. Situated on approximately 0.83 acres with 114 feet of pristine lake frontage, this remarkable residence was designed to capture breathtaking panoramic water views, spectacular sunrises, and unforgettable sunsets from nearly every major living space. Encompassing 6,457 square feet of heated living area, the home seamlessly integrates architecture and landscape through expansive walls of glass, soaring ceilings, refined finishes, and an abundance of natural light. Every space was carefully oriented to maximize the connection between the interior and the surrounding waterfront setting. The designer chef’s kitchen showcases premium Sub-Zero and Wolf appliances, custom European cabinetry, an oversized waterfall island, Italian marble accents, and contemporary finishes, making it both a stunning focal point and an ideal space for entertaining. Designed for flexibility and comfort, the residence features six private bedroom suites, including two luxurious primary suites—one conveniently located on the main level and another on the second floor. Both primary retreats offer spa-inspired bathrooms with elevated finishes, expansive custom closets, premium TOTO fixtures, and living spaces that blend comfort and sophistication. The home also includes eight full bathrooms, one half bath, a dedicated wine room with elegant Italian marble detailing, wide-plank engineered hardwood flooring throughout, designer lighting, dual laundry rooms, a natural gas fireplace, and fully integrated Control4 smart home automation. Control4 home automation allows seamless control of lighting, audio, security cameras, pool equipment, and HVAC systems, creating a connected living experience. Outdoor living is equally impressive, featuring expansive covered lanais, a summer kitchen, saltwater pool and spa, and a private two-level covered dock equipped with water, electricity, and a boat lift. Designed for the ultimate waterfront lifestyle, the dock accommodates a 25-foot boat and two jet skis while providing direct access to the Butler Chain of Lakes, one of Central Florida’s most sought-after boating destinations. Constructed with exceptional attention to detail, the residence features concrete block construction on the main level, metal-frame construction on the second floor, DensGlass exterior sheathing for enhanced durability and weather resistance, energy-efficient TPO roofing, advanced spray foam insulation, four Daikin variable-speed HVAC systems with a combined 20-ton capacity, and natural gas tankless water heaters with recirculation technology. The garage is also equipped with dual 220V outlets for future EV charging capability. Located within the historic Town of Windermere, residents enjoy a unique golf-cart-friendly lifestyle with access to community parks, tennis courts, playgrounds, private lake amenities, and charming tree-lined streets, and the added benefit of no HOA, all while being just minutes from Orlando’s finest dining, shopping, world-class golf, and top-rated private schools. A rare offering on Lake Butler, where architectural excellence, luxury finishes, advanced technology, and one of Central Florida’s most coveted waterfront settings come together to create an exceptional living experience.

728 Forest Street, Windermere

Listing courtesy of S2J REALTY, LLC. 407-745-6023
$1,750,000
4 Beds ⋅ 3 Baths ⋅ O6413242 MLS
Set behind the gates of Windermere Club, this lakefront residence delivers everyday comfort with a resort-style backdrop on beautiful Lake Crescent. Offering 4 bedrooms and 3 baths, the home is designed for easy living and effortless entertaining, with bright, open gathering spaces that keep the water views front and center. At the heart of the home, the kitchen pairs generous prep space with a welcoming bar and an adjacent dining area that comfortably seats six, while a separate formal dining room adds flexibility for holidays and special occasions. The main living area is wrapped in expansive windows, filling the home with natural light and framing tranquil lake scenery throughout the day. Step outside to a covered lanai and screened pool area ideal for quiet mornings, sunset dinners, and everything in between. Take a dip in the saltwater pool, now enhanced with a new pool heater and an Aqua Link pool & spa control system for simple, modern management. The primary suite is a private retreat with captivating lake views and a spa-like bath featuring large windows overlooking a secluded courtyard. Three additional bedrooms provide plenty of space for family, guests, or a home office setup. For true lakefront living, enjoy the newer dock with a covered boat lift, perfect for skiing, cruising, kayaking, or paddle boarding whenever the mood strikes. Upgrades and highlights include double pane windows and sliding glass doors, Shark Coating garage floors, a water purifier, Paradise Grill outdoor kitchen with cover and TV, new pool heater, two brand new AC units, a new water heater, plus additional notable improvements throughout. This is the Windermere waterfront lifestyle, refined, relaxed, and ready to enjoy. Be sure to click on the virtual tour links.

2503 Butler Bay Drive N, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396
$520,000
3 Beds ⋅ 3 Baths ⋅ O6412095 MLS
RARE OPPORTUNITY IN WINDERMERE LANDINGS! Beautifully upgraded 4-bedroom home in one of Windermere's most desirable communities, just steps from Windermere Preparatory School. Originally designed with an expansive downstairs living and family room layout, the spacious loft was thoughtfully converted into a versatile fourth bedroom, creating exceptional value rarely found at this price point. The result is a flexible floor plan ideal for families, remote work, guests, or a growing household. Pride of ownership shines throughout this one-owner home. Elegant porcelain tile flooring, custom wood accent walls, designer finishes, and abundant natural light create a sophisticated yet welcoming atmosphere. Every detail has been carefully maintained and thoughtfully enhanced. The location is simply unmatched. Enjoy a short walk to the community pool and playground, while being just minutes from top-rated schools, shopping, dining, and everyday conveniences. Disney, major attractions, and Orlando's world-class entertainment are only a short drive away. Whether you're searching for a primary residence, a relocation home, or an investment in one of Central Florida's most sought-after areas, this property delivers the perfect combination of location, upgrades, functionality, and value. Homes offering this level of quality, flexibility, and proximity to Windermere Prep rarely become available. Schedule your private showing today.

6412 Golden Dewdrop Trail, Windermere

Listing courtesy of URBAN-O REAL ESTATE SOLUTIONS. 407-822-1063
$3,750,000
5 Beds ⋅ 6 Baths ⋅ O6412077 MLS
Under Construction. Experience unparalleled luxury in this custom-built Davila Homes estate, ideally located in the heart of Windermere. Showcasing the highly sought-after Stanford floor plan, this magnificent residence offers approximately 6,182 square feet of living space with 5 bedrooms, 5 full baths, 1 half bath, and a spacious 3-car garage. Designed for both elegant entertaining and comfortable everyday living, the home features a grand foyer with soaring ceilings, expansive living and family rooms, a private study, and a spectacular gourmet kitchen with an oversized island, walk-in pantry, and premium finishes throughout. The luxurious first-floor owner's retreat serves as a private sanctuary with a spa-inspired bath, oversized walk-in closets, and direct access to the outdoor living areas. Upstairs, you'll find additional en-suite bedrooms surrounding a spacious loft and bonus room, providing the perfect space for family gatherings, a media room, or guest accommodations. Large covered lanais seamlessly blend indoor and outdoor living, creating an ideal setting for entertaining while enjoying Florida's year-round lifestyle. Situated in prestigious Windermere, this exceptional estate combines timeless architecture, thoughtful design, and superior craftsmanship, all within close proximity to top-rated schools, world-class golf, fine dining, shopping, and the Butler Chain of Lakes.

9960 6th Street, Windermere

Listing courtesy of NOVA REAL ESTATE SERVICES INC. 407-592-1744
$449,000
3 Beds ⋅ 3 Baths ⋅ O6397124 MLS ⋅ N/A BLDG.
Virtually Staged. Seller may consider buyer concessions if made in an offer ~ Welcome to Lake Burden South, where this immaculately maintained 3-bedroom, 2.5-bath END UNIT townhome delivers the space, style and location you have been searching for in the perfect Windermere location! Brand new A/C unit installed 8/18/26! Formerly the MODEL HOME for the community, this residence showcases UPGRADED FINISHES, TIMELESS DESIGN elements and a thoughtful layout that feels both functional and elevated from the moment you step inside. Crown molding, abundant natural light and move-in ready condition create a polished feel throughout, while the walkable community setting puts shopping, dining and everyday conveniences just moments away. The main floor offers defined yet connected living and dining spaces, creating a natural flow for both entertaining and daily living. The UPGRADED KITCHEN feels classic and refined with sleek granite countertops, 42” cabinetry topped with crown molding, STAINLESS STEEL APPLIANCES, pantry storage and a large ISLAND with bar seating. A wall of windows keeps the entire space light and bright, while the adjacent breakfast nook and direct access to the PRIVACY FENCED PAVER PATIO make indoor/outdoor living effortless. A convenient half bath for guests, plus a rear-facing 2-car garage, add even more functionality. Upstairs, the spacious PRIMARY SUITE is privately positioned on one side of the home and features a WALK-IN CLOSET along with a beautifully upgraded en-suite bath complete with dual sinks, a SOAKING TUB and a WALK-IN SHOWER with CUSTOM TILE SURROUND. Two additional bedrooms are situated on the opposite side of the second floor and share a full bath, while the LOFT area includes a built-in desk for added flexibility and storage. Residents of Lake Burden South enjoy access to a COMMUNITY POOL and an unbeatable Windermere location with easy access to Winter Garden Vineland Road, nearby lakes, shopping, dining, entertainment and area attractions including Disney parks. Whether you are searching for a beautiful primary residence, a vacation home near Central Florida’s top destinations or a strong investment opportunity, this townhome checks every box. Call today to schedule a tour!

7330 Brightland Street, Windermere

Listing courtesy of WEMERT GROUP REALTY LLC. 407-214-3967
$2,899,000
7 Beds ⋅ 6 Baths ⋅ O6409406 MLS
Located in one of Windermere’s most sought-after luxury GATED communities with 24-HOUR SECURITY-SCREENED ENTRY, Casabella, this exceptional custom-enhanced ESTATE showcases ultra-modern design, refined craftsmanship, and elevated INDOOR-OUTDOOR LIVING, offering impressive scale, custom design, and an exceptional lifestyle experience. Designed with both scale and functionality in mind, the home features an OPEN-CONCEPT floor plan with 7 BEDROOMS, including a beautifully appointed MAIN-LEVEL Primary Suite with a spa-inspired bath, freestanding soaking tub, expansive dual custom-designed walk-in closets, oversized glass-enclosed shower, and integrated STEAM SAUNA. The main floor also includes an additional GUEST SUITE and 2 HALF BATHS. Upstairs, 5 additional BEDROOMS, 2 FULL BATHROOMS, and a spacious LOFT create a well-designed secondary living retreat, offering flexibility for gathering, relaxation, and elevated everyday living. The expansive DESIGNER-ENHANCED GOURMET KITCHEN serves as a striking centerpiece of the home, showcasing imported custom cabinetry, architect-inspired detailing, premium JennAir APPLIANCES, and seamless flow into the GREAT ROOM, multiple dining areas, and surrounding living spaces. Additional interior highlights include a custom-designed EXECUTIVE OFFICE, luxury flooring throughout, ELECTRIC blackout shades, DIGITAL CODE LOCK entry systems on all bedroom doors for added privacy and convenience. Across all 4 FULL BATHROOMS and 2 HALF BATHS, the home showcases floor-to-ceiling tilework, integrated bidet systems, and refined finishes throughout, while 1 HALF BATH offers direct OUTDOOR ACCESS, adding convenience for the POOL and surrounding outdoor living spaces. Designed for both relaxation and everyday enjoyment, the outdoor living experience features a HEATED SALTWATER POOL, SPA, SUMMER KITCHEN, FENCED BACKYARD, and mature PRIVACY LANDSCAPING. Set on approximately 0.63 ACRES, the property also includes a 5-CAR GARAGE with EPOXY FLOORING and AIR-CONDITIONED garage space, an estate-style driveway with exceptional space for car enthusiasts and guests, TESLA CHARGER, FULLY PAID SOLAR PANELS, WATER SOFTENER SYSTEM, and a WHOLE-HOUSE GENERATOR. With proximity to premier GOLF COURSES, scenic LAKES including the Butler Chain of Lakes, top-rated public and private schools, shopping, hospitals, and major roadways, plus convenient access to Disney and Orlando’s premier attractions, Casabella offers privacy, security, and elevated luxury living in one of Windermere’s most desirable communities.

4303 Isabella Circle, Windermere

Listing courtesy of SERHANT. helloflorida@serhant.com
$1,288,999
5 Beds ⋅ 4 Baths ⋅ O6410754 MLS
*** One of the lowest $/SF in Keene's Pointe *** Welcome to this updated, move-in ready luxury home in Keene’s Pointe, one of Windermere’s premier 24-hour guard-gated golf communities and home to the Golden Bear Club. Offering 5 bedrooms, 4 bathrooms, and 3,358 square feet of living space, this beautifully upgraded residence combines luxury finishes, functional design, and an exceptional Central Florida lifestyle just minutes from Disney, top-rated Windermere schools, shopping, dining, and major highways. Situated on an oversized homesite with a large driveway accommodating up to nine vehicles and a three-car garage, this home makes an immediate impression. Inside, the open-concept floor plan features commercial-grade porcelain tile flooring, crown molding, updated lighting, designer finishes, and spacious living areas designed for both everyday living and entertaining. Just off the entry, a custom wet bar with wine refrigerator and beverage fridge flows seamlessly into the dining area and main living space. The updated chef’s kitchen overlooks the family room and showcases quartz countertops, a large center island with additional 36-inch cabinetry storage, a farmhouse sink, soft-close dovetail cabinetry, stainless steel appliances, a natural gas range with vent hood, and an ideal layout for entertaining guests or hosting family gatherings. The spacious first-floor primary suite serves as a private retreat and features a large custom walk-in closet along with a beautifully updated spa-style bathroom complete with dual vanities, soaking tub, oversized walk-in shower with multiple spray features, and custom tile details. Three additional bedrooms and two updated bathrooms are located on the main level, while all bedrooms include custom closet systems and updated ceiling fans. Upstairs, newly finished stairs lead to a versatile loft with luxury vinyl plank flooring, an additional bedroom, and a full bathroom, creating flexible space ideal for a media room, home office, guest suite, or multigenerational living setup. The outdoor living space is designed for Florida entertaining with an approximately 900-square-foot paver patio, natural gas firepit, spacious backyard, and nightly Disney fireworks views. The rear yard is also prewired with 50-amp power for a future pool installation if desired by the next owner. Additional improvements include a 2021 roof replacement, extensive updates throughout the home, a new natural gas meter installed in 2025, and a meticulously maintained septic system with annual servicing over the past 10 years, a new septic alarm box and meter installed in 2021, and a new septic float installed in early 2025. The property also offers exceptional storage with three overhead garage storage racks rated for 600 pounds each, along with a fully planked, lighted, and walkable attic space above the entire three-car garage. Residents of Keene’s Pointe enjoy access to private boardwalks to Lake Tibet and the Butler Chain of Lakes, two community boat ramps, four playgrounds, and year-round neighborhood events. Optional Golden Bear Club membership offers access to championship Jack Nicklaus-designed golf, tennis courts, resort-style pool, fitness center, dining, and social activities. This updated Windermere luxury home offers a rare opportunity to own in one of Central Florida’s most desirable gated golf communities. Schedule your private showing today.

11524 Claymont Circle, Windermere

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

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