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 stunning lakes, lush landscapes, and charming small-town atmosphere, Windermere offers a unique blend of tranquility and modern living. This idyllic community is situated just a stone's throw away from the bustling city of Orlando, making it an ideal location for those seeking a serene retreat without sacrificing convenience.

Windermere is renowned for its beautiful waterfront properties, many of which boast breathtaking views of the pristine Butler Chain of Lakes. The town's commitment to preserving its natural beauty is evident in its well-maintained parks and scenic walking trails, perfect for outdoor enthusiasts and families alike. Enjoy leisurely strolls along the lakefront or partake in various water activities, including fishing, kayaking, and paddleboarding.

The community is also home to a vibrant downtown area, featuring charming boutiques, delightful cafes, and local eateries that reflect the town's warm and welcoming spirit. With a strong emphasis on community events and gatherings, residents often come together to celebrate seasonal festivities, farmers' markets, and outdoor concerts, fostering a tight-knit atmosphere.

Families will appreciate the highly-rated schools in the area, along with the abundance of recreational options, including golf courses, sports complexes, and nature reserves. Whether you're looking to buy your first home, relocate, or invest in a vacation property, the Town of Windermere offers a perfect blend of luxury, leisure, and community spirit. Come experience the charm of Windermere, where every day feels like a vacation!

Newest Listings in Town Of Windermere

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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