Town Of Windermere Homes for Sale

Town Of Windermere Homes for Sale

**Discover the Charm of Windermere: Your Dream Home Awaits**

Nestled in the heart of Orange County, Florida, the Town of Windermere is a picturesque community that perfectly blends natural beauty with modern living. Known for its stunning lakes, lush landscapes, and friendly atmosphere, Windermere is an ideal destination for families, retirees, and anyone seeking a serene yet vibrant lifestyle. With its charming streets lined with oak trees and a welcoming small-town feel, it’s no wonder that many are looking to call this enchanting town home.

Windermere boasts a variety of homes for sale, catering to diverse tastes and preferences. From luxurious waterfront estates with breathtaking lake views to cozy family homes nestled in peaceful neighborhoods, there’s something for everyone. Many properties feature spacious layouts, modern amenities, and beautifully landscaped yards, making them perfect for both relaxation and entertaining.

Residents of Windermere enjoy access to top-rated schools, delightful parks, and a range of recreational activities, including boating, fishing, and hiking. The town’s close-knit community hosts various events throughout the year, fostering connections among neighbors and ensuring a vibrant social scene.

With its combination of natural beauty, exceptional homes, and a warm community spirit, Windermere is more than just a place to live; it’s a place to thrive. If you’re ready to embark on a new chapter in this charming town, explore the homes for sale in Windermere today and find the perfect spot to create lasting memories!

Newest Town Of Windermere Homes for Sale

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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