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! Renowned for its picturesque landscapes and serene atmosphere, Windermere is a hidden gem that offers a perfect blend of luxury and tranquility. This charming city is surrounded by pristine lakes and lush greenery, making it an ideal retreat for families and nature lovers alike.

One of the standout features of homes in Windermere is the abundance of properties boasting private pools. Imagine stepping out into your own backyard oasis, where you can bask in the Florida sunshine or host delightful poolside gatherings with friends and family. These homes are designed to provide both comfort and luxury, allowing you to create lasting memories while enjoying the warm, inviting climate that Florida is famous for.

The Town of Windermere is not only about stunning homes; it also offers a vibrant community atmosphere. With top-rated schools, a variety of parks, and recreational activities, residents enjoy a lifestyle that emphasizes both relaxation and engagement. The local shops and dining options reflect the charming character of the town, providing a delightful experience for all who visit.

Whether you're looking for a peaceful retreat or an active lifestyle, Windermere has something for everyone. The allure of homes with private pools adds an extra touch of luxury, making this town an ideal place to call home. Explore the possibilities and discover your dream home in Windermere today!

Newest Town Of Windermere Homes with Private Pool type

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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