Windermere Real Estate

Welcome to Windermere, Florida – a picturesque subdivision that epitomizes the charm and elegance of suburban living. Nestled in the heart of Orange County, this delightful community is renowned for its stunning landscapes, tranquil lakes, and a strong sense of camaraderie among its residents. With its idyllic setting just a stone’s throw from the vibrant city of Orlando, Windermere offers the perfect blend of serene living and easy access to urban conveniences.

Windermere is characterized by its beautiful tree-lined streets, meticulously maintained homes, and a variety of architectural styles that cater to diverse tastes. From charming single-family homes to luxurious estates, there’s something here for everyone. The community is designed with families in mind, featuring top-rated schools, parks, and recreational facilities that encourage an active lifestyle.

Nature enthusiasts will find solace in Windermere’s abundant outdoor spaces. The area boasts numerous parks, walking trails, and access to the stunning Butler Chain of Lakes, providing ample opportunities for fishing, boating, and enjoying the great Florida outdoors. The community also hosts various events throughout the year, fostering a strong sense of belonging among residents.

Windermere’s prime location means you’re never far from the excitement of Orlando, with its world-famous attractions, shopping, and dining options. Yet, when you return home, you’ll appreciate the peaceful ambiance that Windermere offers.

Discover the charm of Windermere, where community spirit meets serene living, and make this enchanting subdivision your next home sweet home!

Newest Listings in Windermere

$7,500,000

6 Beds ⋅ 8 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code

Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional craftsmanship, and resort-style amenities come together in one of Windermere's most coveted locations. Built in 2024 and spanning approximately 6,900 square feet under air (10,400 total square feet), this custom residence sits on a rare one-acre homesite along the iconic, paved Second Avenue, renowned for its festive holiday displays, spectacular sunsets, and unmatched charm. Designed for both everyday luxury and grand scale entertaining, this 6 bedroom, 7.5 bathroom home offers en-suite bedrooms with walk-in closets, including a private first floor guest suite. The stunning primary retreat features a spa inspired bathroom and a private balcony overlooking the lake, creating the perfect setting to enjoy breathtaking sunsets and nightly Disney fireworks. The heart of the home is a designer chef's kitchen featuring exquisite Cristallo countertops, premium Miele appliances, and seamless flow into the expansive living and entertaining spaces. A dramatic floating wood staircase with a striking stone accent wall serves as an architectural centerpiece, while an elevator provides effortless access to every level. Additional highlights include a custom onyx sink in the powder bath, elegant 8-foot solid wood core doors throughout, motorized blinds, and laundry rooms on both the first and second floors. Step outside to experience a true private resort. The heated infinity edge saltwater pool features a unique acrylic glass viewing wall, allowing swimmers to enjoy underwater lake views unlike anything else. The expansive summer kitchen is equipped with two oversized Big Green Egg grills, a hibachi grill, and generous entertaining areas perfect for hosting unforgettable gatherings. A spacious game room with a full bar, dedicated fitness room, and professionally designed dog run complete the home's exceptional lifestyle offerings. Boating enthusiasts will appreciate the impressive two story private dock with multiple lifts, providing direct access to the famed Butler Chain of Lakes. Car collectors will love the oversized four car garage with an automotive lift, an additional golf cart garage, and an exceptionally long driveway offering abundant guest parking, a rare luxury on Second Avenue. Constructed with impact-rated windows and doors, spray foam insulation, and energy-efficient systems, this home was thoughtfully built to provide superior comfort, security, and efficiency. Combining impeccable design, world-class amenities, spectacular waterfront views, and one of the finest addresses in Central Florida, this remarkable Lake Butler estate represents a rare opportunity to own a nearly new custom home in one of Windermere's most sought after neighborhoods. Be sure to click on the virtual tour links.

724 W 2nd Avenue, Windermere

$2,175,000

6 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code

Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere with excellent walkability. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a stone-framed cooking alcove, premium JennAir® appliances, custom ceiling-height cabinetry, and a walk-in pantry designed for serious cooks and entertainers. The home offers six bedrooms and six bathrooms, with two main-level owner’s suites providing exceptional functionality and privacy. Multiple living spaces are anchored by a striking floor-to-ceiling stone fireplace and beautiful library with rolling ladder, while upstairs bedrooms and bonus room are thoughtfully designed for comfort and quiet, complemented by quality finishes throughout. Recent updates include a newly installed roof (2024) and windows (2025), enhancing both peace of mind and long-term value. A spacious three-car garage adds both convenience and functionality. Outdoors, the home transitions easily to an entertainer’s retreat with covered porches, fireplace, outdoor kitchen, circular firepit, cabana bath, Tiki hut and lush landscaping. The property also offers the opportunity to add a FRONT GATE for enhanced privacy and security, and allows for a FUTURE POOL ADDITION, giving buyers flexibility to further customize the outdoor living experience. Deeded town resident access to the Butler Chain of Lakes and a prime location within Windermere’s vibrant town center with its new redevelopment complete this rare offering where architectural integrity meets a fun and functional Florida lifestyle.

713 Main Street, Windermere

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