Windermere Town Homes with Playground Community Features

Welcome to Windermere Town, a picturesque subdivision nestled in the heart of Windermere, Florida, within the vibrant Orange County. Known for its charming atmosphere and stunning landscapes, Windermere Town offers a serene escape while still being conveniently close to the bustling attractions of Orlando.

This delightful community is perfect for families and individuals alike, boasting a range of beautiful homes that blend modern elegance with classic Southern charm. Each residence is thoughtfully designed to provide comfort and style, ensuring that you feel right at home from the moment you step through the door.

One of the standout features of Windermere Town is its commitment to fostering a strong sense of community. Families will appreciate the well-maintained playgrounds scattered throughout the neighborhood, providing a safe and fun environment for children to play and make lifelong memories. These playgrounds serve as gathering spots for neighbors, encouraging social interactions and a friendly, welcoming atmosphere.

In addition to the playgrounds, residents can enjoy scenic walking trails, lush green spaces, and community events that bring everyone together. Whether it's a weekend picnic or a holiday celebration, Windermere Town thrives on community spirit.

With its prime location, stunning homes, and family-friendly amenities, Windermere Town is not just a place to live; it’s a place to thrive. Discover the charm of Windermere Town and experience the perfect blend of community, comfort, and convenience in one of Florida's most desirable neighborhoods. Your dream home awaits!

Newest Windermere Town Homes with Playground Community Features

$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

$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

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