Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the enchanting Town of Windermere, a hidden gem nestled in the heart of Orange County, Florida. Known for its picturesque landscapes and charming small-town atmosphere, Windermere offers a unique blend of tranquility and luxury, making it one of the most sought-after communities in the Orlando metropolitan area.

As you explore this idyllic subdivision, you'll be captivated by its serene lakes, lush greenery, and beautifully manicured parks. Windermere is bordered by the stunning Butler Chain of Lakes, providing residents with ample opportunities for boating, fishing, and enjoying breathtaking sunsets. The town's commitment to preserving its natural beauty is evident in its numerous walking trails and outdoor recreational spaces, perfect for families and nature lovers alike.

Windermere boasts a vibrant community spirit, with a variety of local events and activities that foster connections among residents. From farmers' markets to seasonal festivals, there’s always something happening in this close-knit town. The highly-rated schools and family-friendly environment make it an ideal place for raising children, while the proximity to Orlando's world-class attractions adds an extra layer of appeal.

With a diverse selection of stunning homes, from luxurious waterfront estates to charming single-family residences, Windermere caters to a range of lifestyles and preferences. Whether you're seeking a peaceful retreat or an active community, this town has it all.

Discover the magic of Windermere, where every day feels like a vacation and life is truly extraordinary. Come and experience the charm of this remarkable subdivision, and make it your forever home!

Newest Listings in Town Of Windermere

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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