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. Known for its picturesque landscapes and serene lakes, this charming community offers a unique blend of suburban tranquility and vibrant living. Windermere is not just a place to call home; it’s a lifestyle filled with outdoor adventures, top-notch schools, and a welcoming atmosphere that fosters a strong sense of community.

One of the most alluring features of homes in Windermere is the abundance of properties with private pools. Imagine stepping out into your backyard oasis on a warm Florida day, where you can unwind in your own sparkling pool, perfect for entertaining guests or enjoying a quiet evening under the stars. Many of these homes boast stunning architectural designs and spacious layouts, providing ample room for families and guests alike.

Living in Windermere means you have access to some of the best recreational activities Florida has to offer. With nearby lakes for boating and fishing, as well as numerous parks and trails for hiking and biking, outdoor enthusiasts will find plenty to explore. The community is also conveniently located near shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away.

Whether you’re looking for a family-friendly neighborhood or a peaceful retreat, Windermere’s homes with private pools provide the perfect haven to relax and enjoy the beautiful Florida weather. Discover your dream home in this idyllic town, where every day feels like a vacation!

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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