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 perfect blend of tranquility and luxury. With its stunning views and friendly atmosphere, Windermere is an ideal place for families and individuals seeking a peaceful retreat from the hustle and bustle of city life.

One of the standout features of homes in Windermere is the abundance of properties boasting private pools. Imagine stepping out of your beautifully designed home and diving into your own oasis, surrounded by lush landscaping and the gentle sounds of nature. These private pools not only provide a refreshing escape from the Florida heat but also create the perfect setting for entertaining friends and family or simply enjoying a quiet evening under the stars.

The homes in Windermere are a testament to fine living, offering a variety of architectural styles and modern amenities. Spacious layouts, gourmet kitchens, and luxurious master suites are just a few of the features you can expect. Many properties are situated on expansive lots, allowing for ample outdoor space, where you can relax by the pool or host unforgettable gatherings.

Windermere is also conveniently located near top-rated schools, shopping centers, and recreational areas, making it an ideal place to raise a family or retire. With its stunning homes featuring private pools and a vibrant community spirit, Windermere truly embodies the essence of Florida living. Come 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

Start Your Search