Windermere Homes with Craftsman Architectural style

Welcome to Windermere, Florida—a picturesque gem nestled in Orange County, where serene lakes and lush landscapes create a tranquil backdrop for a vibrant community. Known for its charming small-town atmosphere, Windermere boasts a rich history and a welcoming spirit, making it an ideal place to call home.

One of the standout features of this enchanting subdivision is its collection of homes designed in the Craftsman architectural style. These residences exude a unique blend of warmth and sophistication, characterized by their low-pitched gable roofs, exposed rafters, and wide front porches—perfect for enjoying the Florida sunshine. Inside, you’ll find open floor plans, handcrafted woodwork, and an abundance of natural light that highlights the exquisite details of each home.

Living in Windermere means embracing a lifestyle that balances relaxation with recreation. The area is dotted with beautiful parks, scenic walking trails, and access to pristine lakes, making it a haven for outdoor enthusiasts. Residents can indulge in various activities, from boating and fishing to picnicking in the park. Families will appreciate the top-rated schools and a strong sense of community, with local events and festivals that bring neighbors together.

Whether you're a first-time homebuyer or looking to settle down in a peaceful environment, Windermere offers an array of Craftsman-style homes that perfectly encapsulate the charm of this delightful community. Discover your dream home in Windermere, where timeless design meets modern living amidst Florida's natural beauty.

$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

Windermere Homes with Craftsman Architectural style

Newest Windermere Homes with Craftsman Architectural style