Town Of Windermere Homes with Private Pool type

Town Of Windermere Homes with Private Pool type

Welcome to the enchanting Town of Windermere, Florida, a hidden gem nestled in the heart of Orange County. Known for its picturesque landscapes and charming small-town feel, Windermere offers a unique blend of luxury and tranquility that appeals to families, retirees, and everyone in between. With its lush greenery, serene lakes, and vibrant community spirit, this town is a perfect escape from the hustle and bustle of city life while still being conveniently located near Orlando's attractions.

One of the most sought-after features in Windermere is the availability of stunning homes with private pools. Imagine stepping into your own backyard oasis, where you can relax and unwind under the Florida sun or host memorable gatherings with friends and family. These homes are designed for both comfort and style, often featuring spacious layouts, modern amenities, and beautifully landscaped yards that enhance the outdoor experience.

Windermere's private pool homes cater to a variety of tastes and preferences, from contemporary designs to classic Mediterranean styles. Many properties are situated near the town’s scenic lakes, offering breathtaking views and easy access to outdoor activities like boating and fishing. The community is also known for its excellent schools, parks, and recreational facilities, making it an ideal place to raise a family.

Whether you’re looking for a serene retreat or an active lifestyle, the Town of Windermere, with its exquisite homes featuring private pools, provides the perfect backdrop for your dream life in Florida. Discover the charm and elegance of Windermere, 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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