The Isle Of Windsor is a neighborhood in Longwood, Florida. The community of Isle of Windsor features unique, custom homes that range in size from 3,000 sq. ft. to 5,000 sq. ft. The community of Isle of Windsor was established and developed in the 1980s. This is an established community that continues to attract interest from buyers looking in the Longwood area. Located a quarter of a mile South of Lake Mary Blvd. off Markham Wood Road, Isle of Windsor has a charming feeling. Residents of the Isle of Windsor enjoy exemplary schools, including The Woodlands Elementary, Markham Woods Middle, and Lake Mary High School. Ideally located, The Isle of Windsor is near the Seminole Wekiva Bike Trail, the Sun Rail, State of the Art Golf Courses, and major roadways.