Windermere Town Homes 

Windermere Town in Windermere, FL, is a charming community nestled in the heart of Central Florida, renowned for its picturesque landscapes and thriving real estate market. The town boasts an array of exquisite homes that cater to diverse tastes, ranging from elegant Mediterranean-style estates to modern suburban residences. This real estate haven offers prospective homeowners a unique blend of luxury and tranquility, making it an ideal destination for those seeking an upscale living experience.

Surrounded by an abundance of natural beauty, Windermere Town provides residents with access to numerous nearby attractions. The pristine Butler Chain of Lakes offers recreational opportunities like boating, fishing, and water sports, catering to outdoor enthusiasts. Additionally, the town's proximity to world-famous theme parks, including Walt Disney World and Universal Studios, ensures that entertainment and family-friendly adventures are always within reach.

Residents of Windermere Town enjoy a plethora of nearby amenities that enhance their quality of life. The town is known for its top-notch schools, making it an attractive option for families seeking an excellent education for their children. Upscale shopping destinations and fine dining establishments are easily accessible, allowing residents to indulge in both retail therapy and gourmet experiences. With its blend of real estate opulence, captivating attractions, and convenient amenities, Windermere Town stands as a testament to the appeal of Central Florida's luxurious lifestyle.

Available Windermere Town Homes For Sale

$840,000
5 Beds ⋅ 3 Baths ⋅ O6414200 MLS
Under contract-accepting backup offers. Offered for the first time, this original 1973 ranch is a rare find in the heart of Windermere. Nestled on an oversized .42-acre lot along a picturesque sand street, this 5-bedroom, 2.5-bath home presents an exceptional opportunity to create your dream property in one of the town's most sought-after locations. Designed with Florida living in mind, the spacious floor plan opens to an oversized screened pool and expansive outdoor living area, perfect for entertaining family and friends. A circular driveway and porte cochere provide convenience and timeless curb appeal, while solid block construction and a newer roof create lasting value. Location is everything. Stroll to charming shops, restaurants, the local brewery, farmers markets, and year-round community events. Enjoy the freedom of a golf-cart-friendly neighborhood with no HOA, plus access to the renowned Butler Chain of Lakes. Whether you're looking to renovate, expand, or build new, this exceptional property offers the perfect canvas. Bring your builder, bring your imagination, and seize this rare opportunity to create something truly special in the heart of Windermere.

412 Forest Street, Windermere

Courtesy of UPSIDE REAL ESTATE INC

$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

Courtesy of S2J REALTY, LLC

$649,999
2 Beds ⋅ 2 Baths ⋅ O6409463 MLS
Under contract-accepting backup offers. Exclusive Rare Opportunity to own this expansive 100'x160' double lot in downtown Windermere. Whether you’re looking for a charming home or a prime location to build your dream residence, this property delivers endless potential. The home features arched doorways, luxury vinyl plank (LVP) flooring, and a sunroom filled with natural light. The updated kitchen includes 42” soft-close cabinets, Granite countertops, stainless steel appliances, and a custom island with a breakfast bar. The primary bedroom boasts a spacious walk-in closet with custom built-ins, and the bathroom is finished with marble and subway tile. The nearly half-acre lot offers a fenced backyard, custom pergola, wood deck, fire pit, and a storage shed with electricity, perfect for entertaining or relaxing. Enjoy walking proximity to Windermere’s cafes, parks, and events like the Farmers Market. Deeded access to the Butler Chain of Lakes and Lake Bessie provides excellent opportunities for boating and water sports. With no HOA, A-rated schools, and golf-cart-friendly streets, this property blends convenience and practicality. Schedule your showing today.

811 Main Street, Windermere

Courtesy of CAMERON REALTY GROUP LLC

$3,900,000
5 Beds ⋅ 5 Baths ⋅ S5148430 MLS
Pre-Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Windermere. Boasting approximately 85 feet of private frontage, The property captures sweeping views across Wauseon Bay. Permits have been approved including a 900 sf covered boat dock with lift. There are 2 primary suites, one on the 1st floor and one on the 2nd that open to a private balcony and patio respectively overlooking the water creating a serene retreat. All secondary bedrooms have lake views and balconies. Open floor plan with 2 story great room and massive windows throughout. 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. ** Also listed as vacant land MLS S5147532 for $1,650,000

212 W 1st Avenue, Windermere

Courtesy of HOME WISE REALTY GROUP, INC.

$1,195,000
4 Beds ⋅ 4 Baths ⋅ O6394569 MLS
SELLER WILL CONTRIBUTE $20,000 TOWARD INTEREST RATE BUY DOWN OR DECORATING ALLOWANCE. Modern style blends with Windermere charm. This totally renovated home is located just steps from Lake Bessie in the Town of Windermere. Set on a beautifully landscaped corner lot with NO HOA, this home combines luxury and comfort in one of Central Florida’s most desirable communities. Every detail has been thoughtfully updated to include roof (2022), a/c (2016), plumbing, flooring, drain field and water filtration system. Inside, sun drenched living and dining spaces flow seamlessly, anchored by a warm inviting fireplace setting the tone for relaxed living and effortless entertaining. The kitchen serves as the heart of the home, featuring soft gray shaker cabinetry, quartz countertops, a generous island with induction cooktop, hood, double wall ovens, mosaic glass backsplash and all new stainless appliances. Sliding doors open to a sparkling pool with sun deck and pergola, surrounded by lush landscaping in a private, fenced courtyard. Whether hosting gatherings or enjoying quiet evenings at home, this outdoor space delivers the true Florida lifestyle. Upstairs, the primary suite features a spa inspired bath with a freestanding soaking tub, rainfall shower, dual sinks, and elegant finishes. Additional bedrooms include an oversized fourth bedroom with its own fireplace and built-ins which easily can be used as a media room, office, or home gym. Located just a short walk or golf cart ride to Windermere shops, restaurants, lakefront parks, weekly farmers markets, library and more, this home places you at the center of it all. Surrounded by the Butler Chain of Lakes and close to renowned golf, fine dining and premium shopping. Windermere offers small town charm yet convenient to major roadways, area attractions and the International Airport. The location is as exceptional as the home itself. This is more than a residence; it is a refined Windermere lifestyle defined by comfort connection and enduring style. SELLER WILL CONTRIBUTE $20,000 TOWARD INTEREST RATE BUY DOWN OR DECORATING ALLOWANCE.

109 E 12th Avenue, Windermere

Courtesy of UPSIDE REAL ESTATE INC

$950,000
4 Beds ⋅ 3 Baths ⋅ TB8495717 MLS
Set on a prominent corner lot in one of Windermere’s most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level, massive multiple garages and a lifestyle that is uniquely local to this area. Relax on the expansive front porch and take in the surroundings as neighbors and nature pass by. Recent improvements include a new roof, a fully renovated kitchen, a designer-inspired primary bath, fresh interior and exterior paint, and newer engineered wood flooring, creating a cohesive, move-in ready home with a refined, modern feel. The layout offers expansive living spaces filled with natural light, designed for both everyday comfort and effortless entertaining. The primary suite serves as a true retreat, highlighted by a beautifully reimagined bath featuring a freestanding soaking tub, custom tile work, and a double vanity. Additional living areas and a spacious lower level provide flexibility for a media room, home office, fitness space, or guest accommodations. A rare offering in this location, the property features an impressive 3 bay, 30' long garage on one end and an additional garage bay on the opposite end of the home., ideal for collectors, storage, or workshop needs. Positioned along historic Windermere’s signature tree-lined dirt roads, the setting offers a level of charm and privacy that is increasingly hard to find. Residents enjoy exclusive access to city tennis courts and a private dock with entry to the interconnected lake chain that surrounds this community, delivering a true lake lifestyle just moments from home. Seller is open to negotiating a closing cost credit, providing added flexibility and value for buyers for closing costs or rate buy down. A compelling combination of location, scale, and thoughtful updates—this is Windermere living at its best.

1002 Oakdale Street, Windermere

Courtesy of KELLER WILLIAMS SUBURBAN TAMPA

$1,175,000
4 Beds ⋅ 3 Baths ⋅ S5147648 MLS
A beautiful home in the heart of downtown Windermere, this property offers four bedrooms and three bathrooms with a perfect blend of comfort, style, and convenience. The main residence features hardwood floors throughout, spacious living areas, and large sliding doors that open to a serene, beautiful backyard — ideal for both entertaining and unwinding. An added highlight is the fully equipped separate dwelling on the property offering a private one-bedroom, one-bathroom space perfect for entertaining, or a home office/gym. Situated just minutes from local shops, parks, boat ramps, and the renowned Windermere Chain of Lakes, this home places the best of the area right at your doorstep.

715 Magnolia Street, Windermere

Courtesy of IRIS INTERNATIONAL

$1,650,000
S5147532 MLS
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. There is an option to build a new home and boat dock, Permits have been approved to build a new modern home and 900sf covered boat dock with lift. This option would be $3.9MM See listing S514430 *** Although this listing is being sold for the land value the home is in good condition and ready to move in. The interior showcases a refined yet comfortable design with an 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.

212 W 1st Avenue, Windermere

Courtesy of HOME WISE REALTY GROUP, INC.

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