Town Of Windermere Homes with Boatable Water Water Frontage

Town Of Windermere Homes with Boatable Water Water Frontage

Welcome to the enchanting Town of Windermere, nestled in the heart of Orange County, Florida. Known for its picturesque landscapes and serene atmosphere, Windermere is a charming community that offers a perfect blend of suburban tranquility and vibrant living. With its stunning lakes, lush greenery, and friendly neighborhoods, this town is truly a hidden gem in Central Florida.

One of the standout features of Windermere is its access to boatable water, making it an ideal destination for water enthusiasts and nature lovers alike. Imagine waking up to the soothing sounds of water lapping against the shore, with the opportunity to hop on your boat for a leisurely cruise or a day of fishing. Many homes in Windermere boast direct waterfront access, allowing residents to enjoy a lifestyle that embraces the beauty of Florida’s lakes.

The real estate options in Windermere are as diverse as its residents. From luxurious waterfront estates to charming family homes, each property reflects the town's unique character and charm. With spacious layouts, modern amenities, and breathtaking views, these homes are designed for comfort and elegance. The community also prides itself on its top-rated schools, parks, and recreational facilities, ensuring that families have everything they need to thrive.

Whether you’re looking to settle down in a peaceful lakeside retreat or seeking an active lifestyle filled with outdoor adventures, Windermere offers the perfect backdrop for your dream home. Come explore this captivating town and discover the endless possibilities that await you on the water!

Newest Town Of Windermere Homes with Boatable Water Water Frontage

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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