Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the Town of Windermere, a picturesque gem nestled in Orange County, Florida. Known for its serene lakes and lush landscapes, Windermere is an idyllic community that captures the essence of Florida living. With its charming small-town atmosphere and stunning waterfront views, this subdivision offers a unique blend of tranquility and sophistication.

Windermere is characterized by its stunning homes, many of which are elegantly designed and situated on spacious lots. The architecture ranges from modern masterpieces to classic Floridian styles, ensuring that there’s something for everyone. Residents enjoy a strong sense of community, with friendly neighbors and a variety of local events that foster connections and camaraderie.

Nature enthusiasts will love Windermere’s abundant outdoor activities. The town is surrounded by beautiful lakes, including the renowned Lake Butler, perfect for boating, fishing, and kayaking. The scenic trails and parks offer ample opportunities for hiking, biking, and enjoying the Florida sunshine. Additionally, the nearby Butler Chain of Lakes provides an impressive backdrop for those who appreciate the great outdoors.

Windermere’s prime location also affords easy access to major highways, making commutes to downtown Orlando and other surrounding areas a breeze. With top-rated schools, upscale shopping, and fine dining options just a stone’s throw away, residents have everything they need right at their fingertips.

Whether you’re looking for a family home, a vacation retreat, or an investment opportunity, the Town of Windermere is a fantastic choice. Experience the charm, beauty, and warmth of this enchanting community and discover why it’s one of Florida’s most sought-after destinations.

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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