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Preston Square Windermere Real Estate

Preston Square is a community of single-family detached homes and townhomes located in Windermere. The townhome buildings and single-family homes of Preston Square are built around the neighborhood square that features amenities such as a community pool, a children’s playground, a large park area and more. This neighborhood is located in the Orlando suburb of Windermere, a community that is well-known for its quaint, small town main street and its numerous lakes. Preston Square is just 11 miles southwest of Downtown Orlando and just north of Walt Disney World Resorts.

Preston Square Homes For Sale

2 Properties Found. Page 1 of 1.
Photo of Listing #O6208309
MLS® # O6208309
4 Beds, 3 Baths, 2,105 Sf
Photo of Listing #O6198160
Reduced 1.4%
MLS® # O6198160
3 Beds, 3 Baths, 1,642 Sf

Preston Square Community Information

Location: Winter Garden Vineland Road and Overstreet Road
Year Built: 2008 - 2012
Total Properties: 68 Townhomes; 75 Single-Family Houses
Builder: Meritage Homes of Florida; Centerline Homes
Square Feet: Townhomes: 1,079 - 2,158; Single-Family Houses: 1,593 - 3,446
HOA: Yes
Community Amenities: Community Pool, Basketball Court, Children’s Playground, Park area

Preston Square, a neighborhood of 75 single-family homes and 68 townhomes, is located just south of Lake Sayer in the community of Windermere. This neighborhood is an ideal choice for homeowners who enjoy a walkable community as even the homesites on the edge of this subdivision are still just a short trek on foot to the neighborhood square. Homeowners in Preston Square enjoy residing in the family-oriented area of Windermere with its quaint, small town main street and numerous options for outdoor recreation, while also being just a short drive to all the top-notch shopping, attractions and eateries Orlando offers.

Townhomes in Preston Square range from two to four bedrooms, while the detached single-family homes range from three to five bedrooms. Both the townhomes and detached single-family homes range from two to four bathrooms.

Preston Square is designed like the historic neighborhoods in Savannah, Georgia, where the neighborhood park is placed in the center of the community, which gives many homeowners in the neighborhood a scenic view of the park from their front porch. And, unlike other planned subdivisions, Preston Square’s amenities center is located in the middle of the neighborhood, so it’s within walkable distance to all residents instead of being located in a corner of the community that makes it close to some residents but far for others. One other uncommon design element for Central Florida subdivisions that is found at Preston Square is the placement of many of the homes driveways and garages at the rear of the home. This allows these houses and townhomes to have smaller front lawns to take care of and gives the facade of a historic neighborhood built pre-automobiles where driveways were not a part of the front yard landscape. Additionally, some homes on the western edge of the community enjoy backyard views of a blueberry farm.

Homeowners at Preston Square have access to a number of neighborhood amenities that are maintained by the homeowners association including a community pool, a children’s playground, a basketball court and a large grassy park area.

Dining and Shopping

  • Lake Burden Shops, Walgreens - Distance: 0.1 Miles
  • Lakeside Village Center, Publix Super Market - Distance: 0.8 miles
  • Restaurant Row - Distance: 4.1 miles
  • Winter Garden Village Retail Shopping Center with Super Target - Distance: 4.2 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 8.0 miles
  • Downtown Orlando - Distance: 11.2 miles

Parks and Recreation

  • R.D. Keene Park, Sporting Fields & Public Boat Ramps - Distance: 1.5 miles
  • Tibet-Butler Preserve, Vera Carter Environmental Center & hiking trails - Distance: 1.8 miles
  • West Beach Park, Playgrounds, Sand Volleyball Court, Beach - Distance: 2.7 miles
  • Lake Down Public Access Boat Ramp - Distance: 3.5 miles
  • Dr. P. Phillips YMCA Family Center - Distance 4.4 miles


  • Florida Hospital Winter Garden - Distance: 4.5 miles
  • Dr. P. Phillips Hospital - Distance: 5.6 miles

*Distances are approximately measured from the Preston Square community entrance.


All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on June 20th, 2024 at 6:49pm EDT.