Town Of Windermere Homes with Private Pool type

Town Of Windermere Homes with Private Pool type

Welcome to the enchanting Town of Windermere, a picturesque gem nestled in Orange County, Florida. Known for its stunning lakes, lush landscapes, and a vibrant community spirit, Windermere offers a serene retreat just a stone’s throw away from the hustle and bustle of Orlando. This charming town is not only known for its scenic beauty but also for its delightful neighborhoods, making it a sought-after destination for homebuyers looking for a tranquil lifestyle.

One of the standout features of Windermere is its array of beautiful homes with private pools. Imagine stepping into your own backyard oasis where you can unwind and soak up the Florida sun. These homes are designed for both relaxation and entertainment, providing the perfect setting for family gatherings, summer barbecues, or simply enjoying a quiet evening under the stars. The private pools are often complemented by lush landscaping, creating a serene atmosphere that enhances the overall charm of your living space.

Windermere boasts a close-knit community with excellent schools, parks, and recreational facilities. Residents enjoy access to a variety of outdoor activities, from boating on the pristine lakes to exploring the scenic trails that wind through the area. With its friendly neighborhoods and a strong sense of community, Windermere is more than just a place to live; it’s a place to thrive.

Whether you’re looking for a family home or a serene retreat, Windermere’s homes with private pools offer the perfect blend of luxury and comfort. Come and discover the beauty of Windermere, where your dream home awaits!

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

Start Your Search

How much is your home worth?

Get instant property value now!