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 charming small-town atmosphere, making it a perfect retreat for families and individuals alike. With its proximity to the vibrant city of Orlando, Windermere offers a unique blend of tranquility and convenience, allowing residents to enjoy both the peacefulness of suburban life and the excitement of urban amenities.

One of the standout features of homes in Windermere is the abundance of properties with private pools. Imagine basking in the warm Florida sun, sipping your favorite drink, and taking a refreshing dip in the comfort of your own backyard. These homes provide an oasis of relaxation and entertainment, perfect for hosting summer barbecues or enjoying quiet evenings under the stars. With a variety of architectural styles and sizes, you’re sure to find a home that perfectly fits your lifestyle and aesthetic preferences.

Windermere is also known for its exceptional schools, vibrant community events, and outdoor recreational opportunities, including scenic parks and walking trails. Whether you're exploring the local farmers' market or enjoying a leisurely day on the water, Windermere offers a lifestyle that is both enriching and relaxing.

If you are seeking a serene community with stunning homes featuring private pools, look no further than the Town of Windermere. Here, you can create lasting memories in a place that feels like home. Come discover the charm and beauty that await you in this idyllic Florida town!

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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