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 stunning lakes, lush landscapes, and a charming small-town atmosphere that beckons families and individuals alike. With a rich history and a vibrant community spirit, Windermere offers a unique blend of tranquility and convenience, making it one of Florida's most desirable places to call home.

One of the standout features of Windermere is its array of exquisite homes, many of which boast private pools that create an oasis of relaxation right in your backyard. Imagine stepping out into your own personal paradise, where sunny afternoons can be spent lounging by the poolside, hosting barbecues, or enjoying a refreshing swim after a long day. These homes are designed for both comfort and entertainment, featuring spacious layouts, modern amenities, and beautiful outdoor living spaces that enhance the Florida lifestyle.

The Town of Windermere is also conveniently located near a variety of shopping, dining, and recreational options. With top-rated schools and a strong sense of community, it’s no wonder families are drawn to this idyllic locale. Whether you’re looking for a serene retreat or a vibrant community to raise your children, Windermere has it all.

Discover your dream home with a private pool in this charming town, where every day feels like a vacation. Embrace the Windermere lifestyle and make your move to this beautiful community 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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