Town Of Windermere Homes for Sale

Town Of Windermere Homes for Sale

Welcome to the enchanting Town of Windermere, nestled in the heart of Orange County, Florida. Known for its picturesque landscapes and serene lakes, Windermere offers a unique blend of small-town charm and modern amenities. This idyllic community is surrounded by the natural beauty of the Butler Chain of Lakes, providing residents with a tranquil lifestyle and abundant recreational opportunities, from boating to fishing and scenic walks along the waterfront.

Windermere is not just a place to live; it's a vibrant community where neighbors become friends. With its top-rated schools, lush parks, and a variety of local shops and restaurants, Windermere fosters a warm and welcoming atmosphere for families, retirees, and everyone in between. The town's commitment to preserving its natural beauty is evident in its well-maintained parks and green spaces, making it an ideal setting for outdoor enthusiasts.

If you’re considering a move to this charming town, you’ll be delighted to discover a range of homes for sale that cater to diverse tastes and budgets. From luxurious waterfront estates with stunning views to cozy family homes nestled in quiet neighborhoods, Windermere’s real estate market offers something for everyone. Each property reflects the town's unique character, with many featuring spacious yards, modern amenities, and easy access to the area's best attractions.

Explore the homes for sale in Windermere, and let the allure of this beautiful town capture your heart. Whether you’re looking for a peaceful retreat or an active lifestyle, Windermere is the perfect place to call home. Discover your dream home today!

Newest Town Of Windermere Homes for Sale

101 Lee Street, Windermere
$1,395,000
5 Beds ⋅ 4 Baths ⋅ Town Of Windermere SubDv. ⋅ 34786 Zip Code
Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-rich home offers nearly 4,200 square feet of versatile living space just steps from Windermere's charming downtown. Situated on nearly half an acre, this five-bedroom, four-bath residence pairs distinctive architectural character with thoughtful updates, abundant natural light and exceptional flexibility. The main living level brings together the kitchen, dining area and expansive great room, where high ceilings and a striking gas fireplace create a warm and inviting gathering space. Four sets of beautiful, new sliding glass doors open to an expansive balcony overlooking the screened pool, extending the living and entertaining space outdoors. A private-entry in-law suite adds another compelling feature to this unique home, offering exceptional possibilities for multigenerational living, extended-stay guests or a private work-from-home space. This lower level includes two bedrooms, two full baths, spacious living area, and a wet bar with mini-refrigerator. The fifth bedroom, currently enjoyed as a home gym, is also perfect for an office, playroom or hobby room. Privately positioned on its own level, the generous primary suite provides a peaceful retreat with a spacious sitting area and private balcony. Recent, significant investments throughout the property include new windows and doors, three newer HVAC units, new roof September 2026, interior and exterior paint, updated astroturf in the side yard, as well as numerous other improvements, all while preserving the character and scale of this established Windermere home. The pool and patio, featuring a screen enclosure just added in 2020, and newer cabanas, perfect for entertaining, relaxing and enjoying Florida living year-round. The location offers a lifestyle all its own, with downtown Windermere’s weekly farmers market, community events, parks and small-town charm just a short walk or golf cart ride away. Town of Windermere residents also enjoy private access to a boat ramp on the renowned Butler Chain of Lakes, as well as to the town tennis and pickleball courts! Zoned for top rated Windermere Elementary and Olympia High, and situated just minutes from the shopping and dining of The Grove at Isleworth and Restaurant Row, this distinctive home delivers a rare combination of space, flexibility, and character all in a desirable, downtown Windermere location.

101 Lee Street, Windermere

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