Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the enchanting Town of Windermere, a picturesque gem nestled in Orange County, Florida. Known for its breathtaking landscapes and serene lakes, Windermere offers a tranquil escape from the hustle and bustle of city life while still providing easy access to urban amenities.

This charming subdivision is characterized by its stunning waterfront properties, lush greenery, and a close-knit community atmosphere. With its scenic views and pristine lakes, including the renowned Lake Butler, residents enjoy a variety of outdoor activities such as boating, fishing, and leisurely strolls along the waterfront. The town's commitment to preserving its natural beauty is evident in its well-maintained parks and walking trails, making it an ideal setting for families and nature enthusiasts alike.

Windermere is not just about beautiful scenery; it boasts a vibrant community spirit. The town hosts various events throughout the year, from farmers' markets to seasonal festivals, fostering connections among residents and creating a welcoming environment for newcomers. The local schools are highly regarded, making it a sought-after location for families looking to provide their children with an excellent education.

With its proximity to Orlando, residents can enjoy the best of both worlds—peaceful suburban living combined with easy access to the excitement of theme parks, shopping, and dining. Whether you're seeking a family home or a serene retreat, the Town of Windermere offers a unique blend of charm, community, and natural beauty that makes it a truly special place to call home. Discover the allure of Windermere, where every day feels like a vacation!

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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