Preston Square
Preston Square: Local Questions Answered
Where is Preston Square in Windermere?
Preston Square is on land bordered by Winter Garden Vineland Road and Overstreet Road, on Helmsley Circle, Ventnor Drive and Evesham Drive. It is in Horizon West's Lakeside Village, in unincorporated Orange County, with Windermere mailing addresses.
What types of homes are in Preston Square?
Preston Square has 75 single-family homes built from 2008 to 2012 and 68 townhomes built in 2008 and 2009, according to Orange County Property Appraiser records. Single-family homes range from about 1,590 to 3,440 square feet and townhomes from about 1,080 to 2,160 square feet.
How much do homes cost in Preston Square?
Over the past two years (MLS data, October 2026), single-family homes in Preston Square sold 10 times for a median of about $623,000, ranging from about $470,000 to $705,000. Four townhomes sold, for about $350,000 to $470,000. For today's listings, see the top of this page.
What are the HOA fees in Preston Square?
Recent MLS listings show HOA dues of about $99 to $128 per month for single-family homes and about $287 to $315 per month for townhomes as of October 2026. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Preston Square, but check the property tax bill for any special assessments. The association is Preston Square Homeowners Association, Inc.
What schools serve Preston Square?
Orange County Public Schools' 2026-27 school zones place Preston Square in Sunset Park Elementary, Horizon West Middle and Windermere High School.
Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.
Does Preston Square have a community pool?
Yes. Orange County records show a pool on a homeowners association tract of about 2.5 acres on Evesham Drive. Florida's list of special districts includes a Preston Cove CDD, but it is not related to Preston Square.
Can you rent homes in Preston Square short term?
No Preston Square-specific rental rules turned up in our research. HOA documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.
