Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the charming Town of Windermere, nestled in the heart of Orange County, Florida. This picturesque community is a hidden gem that perfectly blends the tranquility of suburban living with the vibrancy of nearby urban amenities. Known for its stunning lakes, lush landscapes, and a strong sense of community, Windermere offers a unique lifestyle that appeals to families, retirees, and everyone in between.

One of the standout features of Windermere is its breathtaking natural beauty. The town is surrounded by the sparkling waters of the Butler Chain of Lakes, providing residents with ample opportunities for boating, fishing, and enjoying serene sunsets. Nature lovers will appreciate the numerous parks and walking trails that weave through the area, making it easy to stay active while soaking in the stunning surroundings.

Windermere is also renowned for its excellent schools, making it an ideal place for families. The community fosters a friendly atmosphere, with local events and gatherings that encourage neighborly connections. From the charming downtown area filled with boutique shops and delightful eateries to the annual Windermere Farmer's Market, there’s always something happening in this vibrant town.

Additionally, Windermere's prime location offers easy access to the bustling attractions of Orlando, including theme parks, shopping centers, and cultural experiences, all while providing a peaceful retreat at the end of the day.

Discover the allure of Windermere, where a warm community spirit meets the beauty of Florida living. Whether you’re looking to settle down or find your vacation home, the Town of Windermere is ready to welcome you with open arms.

Newest Listings in Town Of 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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