Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the Town of Windermere, a picturesque gem nestled in the heart of Orange County, Florida. Known for its enchanting lakes and lush landscapes, Windermere boasts a unique blend of small-town charm and modern amenities, making it one of the most sought-after communities in the Orlando area.

As you explore this delightful subdivision, you’ll discover a vibrant community that takes pride in its rich history and commitment to preserving its natural beauty. The town is surrounded by the sparkling waters of the Butler Chain of Lakes, providing residents with endless opportunities for outdoor activities such as boating, fishing, and kayaking. Stroll through the scenic parks, or enjoy a leisurely bike ride along the scenic trails that wind through the area.

Windermere is not just about stunning scenery; it also offers an array of local shops, fine dining, and cultural attractions. The charming downtown area features quaint boutiques and eateries, where you can savor delectable cuisine and shop for unique treasures. The community hosts various events throughout the year, fostering a strong sense of camaraderie among residents.

Families will appreciate the highly-rated schools and safe neighborhoods that Windermere offers, making it an ideal place to raise children. With its proximity to major highways and attractions like Walt Disney World, residents can enjoy the tranquility of suburban living while still being just a short drive away from the excitement of Orlando.

Discover the allure of Windermere – where community spirit, natural beauty, and a vibrant lifestyle come together to create the perfect place to call home.

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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