Windermere Town Real Estate

Windermere Town Real Estate

Welcome to Windermere Town, a picturesque subdivision nestled in the heart of Windermere, Florida, within the vibrant Orange County. Known for its charming small-town atmosphere and stunning natural beauty, Windermere Town offers a unique blend of luxurious living and a close-knit community feel.

As you stroll through the tree-lined streets of this enchanting neighborhood, you’ll be captivated by the elegant homes that showcase a variety of architectural styles, from Mediterranean-inspired designs to contemporary masterpieces. Each residence is thoughtfully designed, offering spacious layouts, modern amenities, and beautiful landscaping that complements the serene surroundings.

Windermere Town is not just about beautiful homes; it’s a lifestyle. Residents enjoy access to top-rated schools, making it an ideal choice for families. The community is also in close proximity to a plethora of recreational activities, including pristine lakes, parks, and walking trails. The nearby Butler Chain of Lakes offers opportunities for boating, fishing, and enjoying the great outdoors, while the charming downtown area features boutique shops, delightful cafes, and fine dining options.

For those who appreciate the arts, Windermere Town hosts various community events throughout the year, fostering a strong sense of belonging among neighbors. With its convenient location just a short drive from Orlando, residents can easily access world-class entertainment, shopping, and cultural experiences.

Discover the enchanting lifestyle of Windermere Town, where every day feels like a vacation in paradise. Come explore this hidden gem and see why it’s the perfect place to call home!

Newest Listings in Windermere Town

1221 Oakdale Street, Windermere
$1,250,000
Windermere Town SubDv. ⋅ 34786 Zip Code
Build Your Dream Lakefront Home in the Town of Windermere! Opportunity is knocking in one of Central Florida’s most desirable areas! This exceptional one-acre lakefront homesite on Oakdale Street in the town offers a rare opportunity to bring your vision to life and build the custom home you have always dreamed of. With an impressive 105 feet of direct frontage on beautiful Lake Bessie, this property provides the space, privacy, and waterfront setting to create something truly special. One of the biggest advantages of this property is NO HOA. Enjoy the freedom and flexibility that comes with owning your own piece of land without the restrictions and monthly fees often associated with planned communities. Whether you envision a stunning custom estate, a spacious family home, or a private lakeside retreat, this property gives you the opportunity to create a home that is uniquely yours. The expansive one-acre lot provides plenty of room to design the lifestyle you want. Imagine a beautiful custom residence with expansive living spaces, a resort-style pool, outdoor entertaining areas, lush landscaping, a private garden, oversized garage, and breathtaking views of Lake Bessie. With 105 feet of lake frontage, you can take full advantage of the waterfront setting and enjoy the beauty and tranquility of lakefront living right in the heart of Windermere. Instead of settling for someone else’s floor plan, start with a blank canvas and create a home designed around the way you live. Bring your architect, builder, and ideas and transform this exceptional homesite into your own private sanctuary. Location is everything, and this property offers the best of the Old Windermere lifestyle. Ideally located within a short distance of the Windermere Farmers Market, local shops, restaurants, and more, while beautiful Lake Butler is just blocks away. Town residents also have access to a boat ramp on Lake Butler and Lake Bessie, along with tennis courts, providing even more opportunities to enjoy the outdoors and the unique lifestyle that makes Windermere so desirable. Windermere is known for its beautiful lakes, charming community atmosphere, desirable residential neighborhoods, and convenient proximity to everything that makes Central Florida such a sought-after place to live. Opportunities to own a large lakefront homesite with no HOA and 105 feet of Lake Bessie frontage are truly special. This is your opportunity to stop dreaming about the perfect home and start building it. Make your vision come to life. Make this exceptional Windermere lakefront property the place you call home. Don't miss this rare opportunity!

1221 Oakdale Street, Windermere
104 E 1st Avenue, Windermere
$1,280,000
4 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Experience the charm of Old Windermere at 104 E 1st Ave, ideally situated in the heart of one of Central Florida’s most sought-after communities. Set on an oversized 0.45-acre corner lot surrounded by mature landscaping, this beautifully reimagined single-story home offers 4 bedrooms, 2.5 bathrooms, 2,441 square feet of living space, and a 2-car garage. Transformed through an extensive renovation by Davila Homes, the residence was thoughtfully redesigned and expanded, creating the feel of a brand-new home while preserving the charm of its Old Windermere setting. The interiors showcase elevated finishes throughout, including a beautifully designed gourmet kitchen with top-of-the-line appliances, sophisticated living spaces, and carefully selected details throughout. Outside, the home embraces the Florida lifestyle with a private pool and outdoor kitchen, creating an ideal setting for entertaining, weekend gatherings, or simply enjoying the privacy and space of nearly half an acre. What truly sets this property apart is its Old Windermere location. Enjoy the character and lifestyle of living within the Town of Windermere, surrounded by tree-lined streets and just moments from local parks, dining, shopping, community events, and everything that makes this area so special—all with no HOA. Combining the character of Old Windermere with the quality, design, and finishes of a beautifully renovated home, 104 E 1st Ave offers a rare opportunity to enjoy nearly half an acre, exceptional indoor-outdoor living, and a truly turnkey residence in the heart of Windermere.

104 E 1st Avenue, Windermere
515 W 2nd Avenue, Windermere
$3,300,000
4 Beds ⋅ 6 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
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. Original house was built in 1961 but completely expanded and remodeled in 2000 - present owner made upgrades in 2023 - call for details

515 W 2nd Avenue, Windermere
212 W 1st Avenue, Windermere
$1,498,000
4 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Virtually Staged. BOAT INCLUDED IN PURCHASE PRICE: 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
715 Magnolia Street, Windermere
$1,089,000
4 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
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
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