Windermere Town Homes with Trail(s) Amenities

Welcome to Windermere Town, a picturesque subdivision nestled in the heart of Orange County, Florida. This charming community is a hidden gem that perfectly blends serene living with modern amenities, making it an ideal choice for families, professionals, and retirees alike.

Windermere Town is renowned for its stunning homes, each designed with elegance and comfort in mind. Many residences feature spacious layouts, contemporary finishes, and lush landscaping, providing a warm and inviting atmosphere. As you stroll through the neighborhood, you'll be captivated by the tree-lined streets and friendly neighbors, creating a sense of community that is both welcoming and inclusive.

One of the standout features of Windermere Town is its access to scenic trails. Residents can enjoy a leisurely walk, jog, or bike ride along beautifully maintained paths that wind through the area, offering the perfect opportunity to connect with nature and stay active. These trails are not only a great way to enjoy the outdoors, but they also foster a vibrant community spirit, as neighbors often come together to explore the local scenery.

In addition to its natural beauty, Windermere Town boasts proximity to top-rated schools, shopping, dining, and recreational facilities. Whether you’re looking for a quiet evening at home or a day filled with adventure, this subdivision caters to all lifestyles.

Experience the charm of Windermere Town, where beautiful homes and inviting trails create the perfect backdrop for your next chapter. Discover your dream home in this idyllic community today!

Newest Windermere Town Homes with Trail(s) Amenities

$850,000

3 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

Welcome to your immaculate and charming home in the heart of Downtown Windermere, where timeless traditional style meets modern convenience. Nestled beneath beautiful mature oak trees, this inviting property offers a spacious yard and a welcoming front porch perfect for relaxing in a pair of rocking chairs and enjoying the peaceful surroundings. Step through the front door into a light-filled interior featuring freshly painted walls and warm wood-look tile throughout the first floor. Your remodeled kitchen is both stylish and functional, featuring stainless steel appliances, a gas range, and granite countertops, perfect for everyday living and entertaining. Upstairs, the home showcases its original hardwood floors throughout, adding warmth and character. The spacious primary suite features a beautifully updated bathroom with custom cabinetry, walk in closets, granite countertops, and quality finishes. Two additional bedrooms and a full bathroom complete the second floor, providing plenty of space for family, guests, or a home office. The expansive, fully fenced backyard offers endless possibilities. There is ample room for a pool, playset, fire pit, outdoor games, and entertaining creating a wonderful private space to enjoy Florida’s beautiful weather. Ideally located within walking distance of the Windermere Farmers Market, local shops, restaurants, and more, with beautiful Lake Butler just blocks away, this home offers the best of the Old Windermere lifestyle. Additional highlights include a new roof installed in 2025, water softener, and newer AC unit. Don’t miss the opportunity to make this special home your own. Schedule your private showing today!

706 Oakdale Street, Windermere

$1,895,000

4 Beds ⋅ 5 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

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. 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

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