Town Of Windermere Homes with Private Pool type

Town Of Windermere Homes with Private Pool type

Welcome to the enchanting Town of Windermere, nestled in the heart of Orange County, Florida. This picturesque community is renowned for its serene lakes, lush landscapes, and a charming small-town atmosphere, making it an ideal haven for families and individuals seeking a tranquil lifestyle just minutes away from the vibrant city of Orlando.

Windermere boasts an array of stunning homes, many of which feature private pools, offering the perfect oasis for relaxation and entertainment. Imagine stepping out into your backyard to bask in the Florida sunshine or hosting memorable gatherings with friends and family around your own sparkling pool. These residences are designed for comfort and luxury, with spacious layouts and modern amenities that cater to all your needs.

The community is not only about beautiful homes; it also offers a wealth of recreational opportunities. With access to numerous parks, scenic walking trails, and the pristine shores of the Butler Chain of Lakes, residents can enjoy outdoor activities year-round. Windermere’s charming downtown area features delightful shops, cafes, and dining options, making it easy to enjoy a leisurely afternoon or a night out.

Families will appreciate the top-rated schools and a strong sense of community, where neighbors become friends and local events foster connections. Whether you’re looking for a peaceful retreat or an active lifestyle, Windermere, with its captivating homes featuring private pools, is the perfect place to call home. Discover the magic of Windermere and make your dream of living in this idyllic community a reality!

Newest Town Of Windermere Homes with Private Pool type

$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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