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 serene lakes, Windermere offers an idyllic setting for those seeking a tranquil yet vibrant community. This charming town is surrounded by shimmering waters, including the stunning Butler Chain of Lakes, making it a paradise for boating, fishing, and enjoying breathtaking sunsets.

Windermere is renowned for its luxurious homes and upscale neighborhoods, each exuding a unique charm that reflects the area’s rich history and natural beauty. The architectural styles range from contemporary estates to classic Florida designs, ensuring there’s something for everyone. Residents often enjoy spacious lots adorned with lush greenery and majestic oak trees, creating an inviting atmosphere that feels like a retreat from the hustle and bustle of city life.

The town is also home to a vibrant community spirit, with local events and activities that bring neighbors together. The Windermere Farmers Market is a favorite among residents, offering fresh produce, artisanal goods, and a chance to connect with fellow community members. Additionally, Windermere's proximity to Orlando ensures that residents have easy access to world-class dining, shopping, and entertainment, including the famous theme parks.

Families are drawn to Windermere for its highly-rated schools and safe neighborhoods, making it an ideal place to raise children. With its captivating scenery, welcoming community, and convenient location, the Town of Windermere truly embodies the best of Florida living. Discover your dream home in this charming town and experience a lifestyle that is both peaceful and vibrant!

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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