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 friendly community atmosphere, Windermere offers an idyllic setting for families, retirees, and everyone in between. This charming town, with its rich history and small-town charm, is perfectly positioned just a stone’s throw away from the bustling city of Orlando, making it an ideal retreat for those seeking both tranquility and convenience.

Windermere is renowned for its beautiful waterfront properties, many of which boast breathtaking views of the pristine lakes that dot the area. The town is a haven for outdoor enthusiasts, with ample opportunities for boating, fishing, and hiking, all set against the backdrop of Florida's natural beauty. The scenic Windermere Chain of Lakes provides a serene environment for residents to enjoy leisurely afternoons and engage in various water activities.

Community is at the heart of Windermere, with a variety of local events and festivals that bring residents together throughout the year. From farmers' markets to holiday celebrations, there’s always something happening in this vibrant town. The highly-rated schools, coupled with a close-knit community feel, make Windermere a fantastic place to raise a family.

With its blend of natural beauty, community spirit, and proximity to urban amenities, the Town of Windermere is not just a place to live; it’s a lifestyle waiting to be embraced. Discover your dream home in this enchanting town and experience the magic of Windermere for yourself!

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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