Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the Town of Windermere, a picturesque gem nestled in the heart of Orange County, Florida. Known for its stunning lakes, lush landscapes, and a close-knit community vibe, Windermere offers an idyllic lifestyle for those seeking both tranquility and convenience.

This charming town is surrounded by the serene waters of the Butler Chain of Lakes, making it a paradise for water enthusiasts and nature lovers alike. Whether you enjoy boating, fishing, or simply taking in the breathtaking sunsets, Windermere's lakes provide a stunning backdrop for outdoor adventures. The town's commitment to preserving its natural beauty is evident in its well-maintained parks and scenic walking trails, inviting residents to embrace an active and healthy lifestyle.

Windermere is not just about natural beauty; it also boasts a vibrant community spirit. With a range of local shops, delightful eateries, and annual events that bring neighbors together, the town fosters a warm and welcoming atmosphere. Families will appreciate the highly-rated schools and safe neighborhoods, making it an ideal place to raise children.

Centrally located, Windermere offers easy access to the bustling city of Orlando, with its world-renowned attractions, shopping, and dining options just a short drive away. This perfect blend of suburban charm and urban convenience makes Windermere a sought-after destination for homebuyers.

Whether you’re looking for a luxurious waterfront estate or a cozy family home, the Town of Windermere is ready to welcome you with open arms. Discover the magic of this enchanting community and make it your new home today!

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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