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

$3,300,000
4 Beds ⋅ 6 Baths ⋅ O6439554 MLS
Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations. This beautifully appointed custom residence offers nearly 4,000 square feet of living space with four bedrooms, soaring ceilings, elegant formal living and dining areas, a spacious kitchen and family room, game room, wet bar, and a thoughtfully designed split-bedroom floor plan. Rich wood and travertine marble flooring, refined architectural details, generous windows bath the main living areas with natural light, and multiple gathering spaces create an atmosphere that is both sophisticated and inviting. A whole house natural gas generator and city water provide peace of mind knowing your family is porotected during the worst Florida storms The primary suite is a private retreat, featuring a luxurious bath with spa-style amenities, a generous walk-in closet, and a serene connection to the surrounding grounds. The home's open living spaces are designed for effortless entertaining, while the separate formal areas provide an elegant setting for more intimate occasions. Outside, the property becomes a private resort. Enjoy the pool and spa surrounded by mature landscaping and expansive outdoor living areas. The private boathouse has a covered boat lift with a "Touchless" Canvas Boat cover that protects your boat from animals and the elements , 2 Jet Ski lifts, Sitting area with fan and mood lighting, Garden hose with city water for cleaning, seawall that has a small beach carved in to allow for playing in the sand of the crystal clear lake, and direct lake access make this an exceptional opportunity for boating, water sports, fishing, and sunset cruises throughout the Butler Chain. Life here extends beyond the property itself. Located on one of Windermere's most desirable paved streets, the home is just moments from the charm of historic downtown Windermere, with its tree-lined streets, local shops, restaurants, parks, community amenities, and small-town atmosphere. Residents enjoy the unique privilege of living among the lakes while remaining conveniently connected to Central Florida's premier dining, shopping, entertainment, and attractions. The Town of Windermere describes its lakes as a beloved community privilege, with the Butler Chain comprising a remarkable network of interconnected waterways. Whether you're enjoying coffee overlooking the water, entertaining beside the pool, stepping aboard your boat for an afternoon on the chain, or returning home to the peaceful canopy of mature trees, this home embodies the very best of Windermere lakefront living.

515 W 2nd Avenue, Windermere

Courtesy of VINTAGE REALTY GROUP LLC

$1,895,000
4 Beds ⋅ 5 Baths ⋅ O6437093 MLS
Set along the shores of Lake Bessie in the heart of Downtown Windermere, this contemporary lakefront residence pairs clean architectural design with effortless single-story living. Completed in 2024, the home offers 2,868 square feet with four bedrooms, each featuring a private en-suite bath, along with a dedicated home office and an open-concept layout designed around the water views. Inside, wide-plank white oak hardwood floors, soaring ceilings and expansive black-framed glass doors create a bright, modern aesthetic while drawing the lake into the main living areas. The European-inspired kitchen anchors the home with an oversized island, quartz countertops, sleek cabinetry and smart appliances, flowing seamlessly into the dining and living spaces for easy everyday living and entertaining. The primary suite continues the home's refined design with a spa-like bath featuring a freestanding soaking tub, floating wood vanity, dual sinks and an oversized walk-in shower. Contemporary finishes and a light, neutral palette carry throughout the residence. Outdoors, a private heated pool and spa create a resort-like retreat, while the lakefront setting offers approximately 100 feet of frontage on Lake Bessie with the option to add a private dock. There is also a two car covered parking area with EV Charger. From morning sunrises and lake breezes to afternoons spent boating or fishing, the setting captures the relaxed lifestyle that makes Windermere so desirable. Just a short walk or golf cart ride from Downtown Windermere, the home places the weekly farmers market, parks, tennis courts, boat ramp to Lake Butler and Bessie, dining, local shops and a brewery within easy reach. Modern architecture, direct lake frontage and an exceptional in-town location come together for a rare opportunity to experience contemporary waterfront living in Windermere

930 East Boulevard, Windermere

Courtesy of CORCORAN PREMIER REALTY

$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

Courtesy of HOME WISE REALTY GROUP, 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

$1,099,000
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

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