Preston Square
Preston Square is a neighborhood in Windermere, FL, with 75 single-family homes and 68 townhomes. The community is built around a central park and features a pool, playground, basketball court, and open green space. It’s a walkable neighborhood where many homes have garages in the back, giving the streets a clean, traditional look. Some homes even back up to a blueberry farm, offering peaceful views.
Community Details
Location: Winter Garden Vineland Road & Overstreet Road
Year Built: 2008 - 2012
Total Homes: 75 single-family homes, 68 townhomes
Builders: Meritage Homes of Florida, Centerline Homes
Home Sizes:
Townhomes: 1,079 - 2,158 sq. ft. | 2 to 4 bedrooms | 2 to 4 bathrooms
Single-Family Homes: 1,593 - 3,446 sq. ft. | 3 to 5 bedrooms | 2 to 4 bathrooms
HOA Fees: Yes
Amenities: Pool, basketball court, playground, and park
Location & Lifestyle
Preston Square is close to shopping, restaurants, and parks. It’s a quiet neighborhood with tree-lined streets but is still a short drive from Orlando’s top attractions.
Nearby Shopping & Dining
Lake Burden Shops & Walgreens – 0.1 miles
Lakeside Village Center (Publix, Restaurants, Shops) – 0.8 miles
Restaurant Row – 4.1 miles
Winter Garden Village (Super Target, Shopping) – 4.2 miles
The Mall at Millenia & BJ’s Wholesale Club – 8 miles
Downtown Orlando – 11.2 miles
Parks & Recreation
R.D. Keene Park (Sports Fields, Boat Ramp) – 1.5 miles
Tibet-Butler Preserve (Hiking Trails, Nature Center) – 1.8 miles
West Beach Park (Playground, Volleyball, Beach Area) – 2.7 miles
Lake Down Public Boat Ramp – 3.5 miles
Dr. P. Phillips YMCA – 4.4 miles
Nearby Hospitals
Florida Hospital Winter Garden – 4.5 miles
Dr. P. Phillips Hospital – 5.6 miles
