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, a picturesque gem nestled in Orange County, Florida. Known for its serene atmosphere and stunning natural beauty, Windermere is a sought-after destination for those looking to embrace a luxurious yet relaxed lifestyle. This charming town is surrounded by pristine lakes, lush landscapes, and vibrant wildlife, making it a haven for outdoor enthusiasts and nature lovers alike.

One of the most captivating features of Windermere is its waterfront properties that boast boatable water frontage. Imagine waking up to breathtaking views of shimmering lakes, where you can step outside your door and hop onto your boat for a day of exploration or fishing. These homes offer not just a residence but a lifestyle filled with adventure and tranquility. Whether you’re cruising along the scenic waters or enjoying a sunset from your private dock, life here is nothing short of magical.

Windermere is also home to a close-knit community, where neighbors become friends and local events foster connections. The town's quaint charm is complemented by its proximity to world-class amenities, including shopping, dining, and top-rated schools. With easy access to major highways, residents can enjoy the best of both worlds—serenity at home and the vibrant energy of nearby Orlando.

If you're seeking a dream home that combines luxury, nature, and community, Windermere's waterfront properties with boatable access are waiting for you. Come discover the beauty and lifestyle that this extraordinary town has to offer!

Newest Town Of Windermere Homes with Boatable Water Water Frontage

$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

Start Your Search