Town Of Windermere Homes for Sale

Town Of Windermere Homes for Sale

Welcome to the enchanting Town of Windermere, a picturesque gem nestled in the heart of Orange County, Florida. Known for its serene lakes and lush landscapes, Windermere offers a tranquil escape while being conveniently close to the vibrant pulse of Orlando. This charming town is celebrated for its small-town atmosphere, where friendly neighbors and community spirit thrive.

Windermere is not just a place to live; it’s a lifestyle. With its stunning waterfront properties and beautifully designed homes, the subdivision boasts a diverse range of real estate options, catering to various tastes and preferences. Whether you’re looking for a luxurious estate with panoramic lake views, a cozy family home in a friendly neighborhood, or a modern townhouse with contemporary finishes, Windermere has something for everyone.

The homes for sale in Windermere reflect the area’s commitment to quality living. Many properties feature spacious layouts, gourmet kitchens, and expansive outdoor areas perfect for entertaining or enjoying the beautiful Florida sunshine. Residents also have access to top-rated schools, upscale shopping, and a plethora of recreational activities, including boating, fishing, and hiking along scenic trails.

Windermere’s charm is enhanced by its rich history and vibrant community events, making it an ideal place for families, retirees, and anyone seeking a serene yet engaging environment. Explore the available homes for sale in Windermere today and discover the perfect setting for your next chapter in this idyllic Florida town. Your dream home awaits!

Newest Town Of Windermere Homes for Sale

$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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