Windermere Homes for Sale

Windermere Homes for Sale

Welcome to Windermere, a charming city located in Orange County, Florida. Known for its picturesque landscapes and luxurious homes, Windermere offers a truly exceptional living experience.

Nestled in the heart of the Sunshine State, Windermere boasts a prime location with easy access to major cities and attractions. Residents enjoy a peaceful and serene environment, surrounded by pristine lakes and lush greenery. With its small-town charm and close-knit community, Windermere is the perfect place to call home.

If you're in the market for a new home, Windermere has a wide range of options to suit every lifestyle and budget. From stunning waterfront properties to spacious family homes, there is something for everyone in this thriving real estate market. Whether you're looking for a modern contemporary design or a classic Mediterranean-style villa, Windermere has it all.

In addition to its beautiful homes, Windermere offers a host of amenities and attractions. The city is home to top-rated schools, making it an ideal choice for families. Outdoor enthusiasts will appreciate the abundance of parks, golf courses, and recreational activities available. And with its close proximity to Orlando, residents can easily access world-class entertainment, shopping, and dining options.

Don't miss out on the opportunity to experience the best of Windermere's real estate market. Explore the homes for sale in this vibrant city and find your dream home today.

Newest Windermere Homes for Sale

$1,650,000
4 Beds ⋅ 2 Baths ⋅ S5155372 MLS
Virtually Staged. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity in the Town of Windermere. Boasting approximately 65 feet of private frontage and a dedicated boat dock, the property captures sweeping views across Wauseon Bay. The current home is in good condition and ready to move in. The interior showcases a refined yet comfortable cabin style with some modern flair and a open-concept layout, four bedrooms and thoughtfully updated living spaces. A beautifully appointed kitchen features custom cabinetry, quartz surfaces, and premium appliances, while restored hardwood flooring adds timeless character throughout. The primary suite opens to a private balcony overlooking the water, creating a serene retreat. Outdoors, the property offers a fenced yard and a rare combination of circular driveway and rear-access garage. Just moments from Windermere’s parks, tennis courts, farmers market, and private boat ramp, this home embodies the charm and lifestyle of lakefront living in one of Central Florida’s most desirable communities. There is an option to build a new home and boat dock, Permits have been approved to build a new modern home 3,500sf and 900sf covered boat dock with lift. This option would be $3.9MM

212 W 1st Avenue, Windermere
$1,499,000
7 Beds ⋅ 5 Baths ⋅ TB8537368 MLS
Introducing a remarkable 2025 two-story luxury residence in the highly sought-after Palms of Windermere, one of Orange County’s premier new-construction communities near Walt Disney World property and neighboring Horizon West. This exceptional home combines expansive living spaces, elevated finishes, and thoughtful design to create a residence that feels both polished and effortlessly comfortable in size. Offering 7 bedrooms and 4.5 bathrooms, this home delivers an abundance of space for family living, guests, entertaining, and flexible yet upscale lifestyle needs. From the moment you enter, the home makes an impression with its oversized rooms, soaring sense of space, luxury light fixtures, stone choices, upgraded flooring, and expansive living areas throughout. The heart of the home holds a beautifully crafted open-concept kitchen, dining room, family room, and living seamlessly flowing living areas—perfectly suited for everyday functionality and memorable gatherings. The gourmet gas-lined kitchen features 42-inch wrap-around cabinetry and countertops, a substantial oversized island, and premium finishes, complemented by upgraded appliances that bring both style and performance to the space. The spacious owner’s suite is a private retreat, featuring a spa-inspired bathroom with an upgraded package, including a glass-enclosed shower, stylish wall niche, and two generous walk-in closets. Throughout the residence, 7 oversized bedrooms and thoughtfully designed spaces provide exceptional comfort and flexibility. The main living area extends seamlessly through 9-foot hidden sliding glass doors to the expansive outdoor living space, creating an effortless connection between the interior and exterior. Step outside to enjoy the 2026 private pool by Dreamscape Pools, surrounded by a 2026 privacy fence, creating a beautifully appointed backyard retreat. With a west-facing orientation, the outdoor space is perfectly positioned to take in gorgeous evening sunsets & Disney Fireworks while entertaining, relaxing, or enjoying time with family. The first floor also offers a versatile flex room ideal for a home office, study, playroom, or additional guest space. Upstairs, the generously sized bedrooms—many featuring walk-in closets— allow privacy and comfort, while three full bathrooms and a convenient second laundry room, in addition to the downstairs laundry, make daily living remarkably functional. The upper level continues to impress with expansive common areas, including a large bonus room and additional flex space that can easily be transformed into a private theater, game room, lounge, gym, or customized entertainment area. An additional standout feature is the oversized garage, providing exceptional room for vehicles, storage, recreational equipment, and everyday household needs. Every detail of this residence is designed around elevated living—from the luxury lighting and upgraded appliances to the oversized rooms, generous storage, expansive garage, and resort-style outdoor living space. The result is a home that offers the scale and comfort of a private estate with the convenience of a premier Horizon West location. Located on the intersection of Reams Road and Ficquette Road, Palms of Windermere places you just minutes from Walt Disney World, Hamlin Town Center, Horizon West’s dining and shopping, and the area’s many neighborhood conveniences. Welcome to a home where luxury, space, and Florida resort-style living come together.

14274 Crest Palm Avenue, Windermere
$1,785,000
4 Beds ⋅ 4 Baths ⋅ O6431500 MLS
Perfectly positioned on the 8th fairway of the renowned Golden Bear Golf Course in Keene's Pointe, this stunning Victorian estate offers timeless elegance, exceptional craftsmanship, and breathtaking golf course views. A grand foyer welcomes you with an impressive circular staircase, setting the stage for the home's sophisticated design and gracious living spaces. The gourmet kitchen is a chef's dream, featuring a large center island, breakfast bar, premium finishes, and seamless flow into the main living areas, where a cozy wood-burning fireplace creates a warm and inviting atmosphere. A wraparound covered front porch adds classic Southern charm and provides the perfect place to relax and unwind. Designed for effortless indoor-outdoor living, the spectacular backyard is an entertainer's paradise. Enjoy a sparkling saltwater pool, gas-heated spa, newly installed outdoor kitchen, and a retractable screened lanai—all overlooking the picturesque fairways of the Golden Bear Golf Course. Located within the highly sought-after gated community of Keene's Pointe, residents enjoy 24-hour guarded security, an award-winning golf course, tennis courts, a resort-style community pool, and an exceptional lifestyle in one of Central Florida's premier neighborhoods. This extraordinary residence offers the perfect blend of luxury, comfort, and breathtaking surroundings.

8241 Tibet Butler Drive, Windermere
$7,000,000
5 Beds ⋅ 6 Baths ⋅ O6430931 MLS
Stately and elegant lakefront estate showcasing the best of Isleworth West. This grand home spans more than 7,000 square feet with 5 bedrooms- of which, four are on the ground floor – plus office, gym, library, storage room, upstairs media room and downstairs bonus room, perched along Lake Louise, the only lake on the Butler Chain surrounded by Isleworth. Expansive formal and living spaces are highlighted by picturesque lake views. The seamless flow from room to room takes full advantage of a layout built for living. The chef’s kitchen with island, gas cooktop, stainless appliances, hidden walk-in pantry, and built-in hutch offer an abundance of space for entertaining or family gatherings. The primary retreat offers an escape from the ordinary with peaceful lake views, a master bath with jetted tub, garden and water view shower, and a showstopping two-story custom closet that will be the envy of all. The executive office with wood walls and built-in shelving offers a luxurious setting for attending to business from home. Three secondary bedrooms on the main floor are all spacious and feature ensuite bathrooms. Upstairs is a fourth bedroom, gym, library, and open media room with balcony. Outdoor amenities include a screened patio with summer kitchen, oversized resort-style pool with travertine decking, large green space, and private dock with covered boat lift plus dock-mounted jet-ski lifts, and 3-car garage. Home also includes a full-house generator. This coveted location within Isleworth West offers an intimate setting with a limited number of homesites and no pass-through traffic. Community is regarded as Central Florida’s most exclusive address with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional membership opportunities.

6055 Louise Cove Drive, Windermere
$550,000
3 Beds ⋅ 2 Baths ⋅ A4702367 MLS
Welcome to this beautiful maintained traditional-style home in the highly desirable Town of Windermere, Florida, just minutes from the renewed Butler-Chain of Lakes. Nestled in a quiet, peaceful neighborhood, this 3-bedroom, 2-bathroom home offers 1,926 square feet of comfortable living space with thoughtful upgrades throughout. The updated kitchen features renovated cabinetry, while both bathrooms have been tastefully upgraded. The spacious primary suite includes a large walk-in closet, and elegant crown molding adds character to the primary bedroom and dining area. Additional highlights include the roof installed four years ago, beautiful tile flooring throughout the home with carpet in the living room and bedrooms, stylish glass shower doors in the secondary bathroom, and an attached two-car garage. Every detail reflects the pride of ownership and care this home has received over the years. Residents also enjoy access to fantastic community amenities, including a swimming pool, tennis courts, and a basketball court, providing opportunities for recreation just steps from home. This is a peaceful retreat with the opportunity to enjoy the sought-after Windermere style. This home is a beautiful place to call your own.

6679 Duncaster Street, Windermere
$1,230,000
5 Beds ⋅ 4 Baths ⋅ O6431068 MLS
From the moment you step inside, this beautiful Mediterranean-style pool home in Enclave at Windermere Landing makes a lasting impression. Offering 5 bedrooms, 4 full bathrooms, nearly 4,000 square feet of living space, and the thoughtfully designed Camellia floor plan, this home blends elegant design, everyday comfort, and inviting spaces for entertaining. The interior features porcelain tile throughout the first floor, a bright open layout, and generous living spaces that flow naturally from the formal dining room to the family room and kitchen. The gourmet kitchen is enhanced with quartz countertops, a large center island, a walk-in pantry, a butler’s pantry, and plenty of space for cooking, hosting, and gathering. The first floor also includes a guest bedroom, ideal for comfortably accommodating visitors. The study is perfect for a private home office. A large game room adds flexible space for movie nights, play, work, or relaxation. Upstairs, the spacious primary suite offers a true retreat with an oversized walk-in closet and a spa-like bathroom with dual vanities, a soaking tub, and a separate shower. The second floor also offers generously sized bedrooms. The upper-level laundry room adds effortless convenience to your daily routine. The backyard is designed for the Florida lifestyle, featuring a private in-ground pool, covered patio, deck space, and a newly added summer kitchen, creating the perfect setting for entertaining or enjoying quiet evenings at home. Both A/C units were replaced in 2024. Located in Windermere, near Keene’s Pointe, Golden Bear Golf and Country Club, Butler Chain of Lakes, shopping, dining, Disney parks, major roadways, and highly rated schools, this home offers the space, features, and location designed for the way you want to live. Don’t miss this rare opportunity to own a beautifully maintained pool home in one of Windermere’s desirable communities. Schedule your showing today!

6443 Swanson Street, Windermere
$695,000
5 Beds ⋅ 5 Baths ⋅ O6429931 MLS
Gorgeous former model home situated on an oversized corner lot with a beautiful private swimming pool! Designed for comfortable living and entertaining, this spacious home offers an exceptional layout and a highly desirable location near Walt Disney World, shopping, dining, and everyday conveniences. Fresh interior and exterior paint gives the home a clean, refreshed feel. The first floor features a generously sized primary bedroom with an en-suite bathroom. The open-concept kitchen overlooks the expansive family room, creating the perfect setting for relaxing afternoons, family gatherings, and entertaining guests. Upstairs, you will find a spacious bonus room with beautiful views, a large full bathroom, two additional bedrooms, and a conveniently located laundry room with the washer and dryer included. Step outside to enjoy the impressive pool and patio area, ideal for entertaining or embracing the Florida lifestyle. The separate detached building offers a garage on the first floor and a private bedroom with a full bathroom above. This versatile space is perfect for a guest suite, home office, studio, or additional living area. A truly special home offering abundant space, flexibility, and an outstanding location with convenient access to Central Florida’s world-famous attractions!

7236 Penkridge Lane, Windermere
$625,000
4 Beds ⋅ 4 Baths ⋅ O6431329 MLS
Welcome to this 4-bedroom, 3.5-bath plus loft residence in the gated community of Belmere Village. Offering 2,837 square feet of thoughtfully designed living space, this home features soaring ceilings, abundant natural light, and a functional floor plan ideal for both everyday living and entertaining. The spacious kitchen is equipped with granite countertops, stainless steel appliances, and a center island. The private primary suite offers a bathtub and a separate walk-in shower. A secondary bedroom includes its own en-suite bath, creating the perfect setup for guests or multigenerational living. Step outside to a covered patio, providing the perfect space to enjoy your morning coffee, dine outdoors, or entertain year-round. Belmere Village residents enjoy resort-style amenities including a community pool, clubhouse, fitness center, and tennis courts. Ideally located near top-rated schools, shopping, dining, and major roadways, with Disney just 34 minutes away and Universal Epic Universe approximately 26 minutes away. This move-in-ready home offers the perfect combination of comfort, convenience, and location.

11854 Via Lucerna Circle, Windermere
$3,500,000
4 Beds ⋅ 6 Baths ⋅ O6430755 MLS
Welcome to the exclusive gates of Isleworth, golf front estate offers over 7,600 square feet of refined luxury living overlooking the fairway of the renowned Isleworth Golf & Country Club, one of the worlds most prestigious golf club communities, this championship course was designed by Arnold Palmer and set along the Butler Chain of Lakes. The neighborhood is defined by beautifully landscaped scenery, sweeping water views, and exceptional 24 hour guard gated privacy. This estate offers exceptional potential supporting four beds, six baths, a private office, inside gym, approached by a private driveway with ample guest parking and a 4 car garage. The two story residence opens with a regal marble foyer and fountain feature. Inside, vaulted ceilings, skylights, and wall to wall sliding glass doors fill the main living areas with natural light while framing views of the pool, sauna, golf views and rolling fairways beyond. A grand fireplace and wet bar create an inviting space for entertaining. The chef’s kitchen centers on a dramatic island and is highlighted by a striking copper range hood, warm cabinetry, and an open eat in layout designed for both everyday living and hosting. Above the garage, a private accessory dwelling unit provides flexible secondary living space or maids living. Each of the spacious bedrooms offers its own view and is finished with marble baths. A dedicated home gym adds further convenience. Exceptional amenities and sophisticated living in the world renowned community of Isleworth.

5524 Worsham Court, Windermere
$3,400,000
6 Beds ⋅ 7 Baths ⋅ S5154885 MLS
Spectacular Private Gated Lakefront Estate on Lake Olivia in Windermere - From the moment you enter through the custom iron gates, you are welcomed into a private lakefront estate unlike any other. Nestled on 1.75 acres along the shores of Lake Olivia, this custom-built Mediterranean residence showcases Tuscan-inspired architecture, mature landscaping, and a winding paver drive creating a true sense of arrival and privacy. Offering six bedrooms, all with ensuite bathrooms, including a private attached mother-in-law suite, this estate features an ideal floor plan with nearly all living spaces and five bedrooms conveniently located on the main level, with the sixth bedroom and bonus/media space upstairs. Elegant craftsmanship is showcased throughout with stone accents, travertine and granite finishes, and refined details. The primary retreat features French doors opening to the screened lanai with pool and lake views, dual custom closets, and a luxurious bath complete with stone flooring, tiled shower, jetted tub with fireplace and mounted TV, dual vanities, private water closet with bidet, and illuminated makeup area. The attached sixth bedroom suite offers a private side entrance, separate kitchen, sitting area, and serene lake views, perfect for guests or multigenerational living. The gourmet chef’s dream kitchen features double islands, granite countertops, premium appliances including a full-size professional Wolf 6-burner and griddle gas range with double ovens, 48” Sub-Zero Pro refrigerator/freezer with lit glass door, food warmer drawer, additional convection oven, wine fridge, and butler’s pantry. Additional highlights include a separate media/games room upstairs, formal living and dining spaces, spacious laundry room with pantry storage, and an oversized 3-car garage with keypad entry, side entrance, and epoxy flooring. The expansive 1,200+ square-foot screened lanai spans the rear of the home and is fully protected with 8 remote hurricane shutters. Enjoy multiple gathering areas overlooking the pool and lake, a summer kitchen with Viking grill, hood, fridge and sink, stone fireplace, teak ceilings, and a breathtaking lagoon-style saltwater pool with heart-shaped spa. Recent enhancements totaling over $200,000 include all-new light fixtures and ceiling fans, whole-house generator with automatic transfer capability restoring power in under 15 seconds during an outage, Leaf Guard gutter system, new AC system, remote hurricane shutters, roof tile servicing and sealing for pest protection, newly installed side pavers, and fresh interior paint. Take in the stunning lake views from the oversized boathouse and screened dock room, featuring a motorized boat lift with direct access to Lake Olivia — a private spring-fed lake with no public access, sandy bottom, and exceptional opportunities for boating, skiing, and fishing. A rare opportunity to own a private lakefront estate with no HOA offering architectural elegance, exceptional entertaining spaces, modern upgrades, and the tranquility of one of Central Florida’s most desirable private lakes. Conveniently located near world-class shopping, major highways, and area attractions. Move-in ready and available for immediate showings with 360 Tour and floorplan available.

9679 Westover Roberts Rd, Windermere
$610,000
4 Beds ⋅ 5 Baths ⋅ O6430484 MLS
Welcome to this beautifully maintained 4-bedroom, 4.5-bath residence situated on a premium 9,055-square-foot corner lot in the highly desirable Wickham Park community of Windermere. Offering 2,192 square feet of thoughtfully designed living space, this two-story home features an open floor plan filled with natural light, spacious living and dining areas, and a private primary suite with a walk-in closet. One of the home's standout features is its expansive backyard, providing exceptional outdoor space rarely found in similar properties. The backyard already includes an above-ground pool, offering the perfect place to relax and enjoy Florida's outdoor lifestyle. There is still plenty of room to create your dream outdoor retreat, whether you envision a summer kitchen, an entertainment area, lush landscaping, or future enhancements tailored to your lifestyle. Perfectly positioned directly across from Horizon West Middle School, this home offers outstanding convenience for families with school-age. The desirable corner-lot location also provides additional street parking along the side of the property, making it easy to accommodate family and guests during gatherings and special occasions. Residents enjoy outstanding community amenities, including a clubhouse, resort-style community pool, and playground, while being just minutes from shopping, dining, major highways, Walt Disney World, and everything that makes Windermere and Horizon West among Central Florida's most sought-after communities. Don't miss this exceptional opportunity to own a beautiful home that combines comfort, functionality, outdoor living, and an unbeatable location in one of Windermere's premier neighborhoods.

12749 Garridan Avenue, Windermere
$539,900
4 Beds ⋅ 3 Baths ⋅ O6430196 MLS
Move-In Ready! Beautifully Updated Home in the Highly Desirable Windermere Area! Welcome to this beautifully refreshed 4-bedroom, 2.5-bath home located in the sought-after Windermere Trails community. Built in 2014, this two-story residence includes approximately 2,074 square feet of living space with an open-concept layout, abundant natural light, and tasteful updates throughout. The kitchen features granite countertops, stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas. The spacious primary suite includes a walk-in closet and an ensuite bath with dual vanities, a soaking tub, and a separate shower. Additional highlights include updated flooring, fresh interior finishes, a covered lanai, and a fenced backyard. Conveniently located near shopping, dining, major highways, Disney, and top-rated schools.

11938 Silverlake Park Drive, Windermere
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