Windsor Hill
Windsor Hill: Local Questions Answered
Where is Windsor Hill in Windermere?
Windsor Hill is on Windsor Hill Drive, Park Royal Drive, Crown Prince Lane and nearby courts, with Windsor Hill Reserve on Castle Way Drive, off Windy Ridge Road. Westover Club borders it to the north. It is in unincorporated Orange County with Windermere, FL 34786 mailing addresses.
What types of homes are in Windsor Hill?
Windsor Hill has 109 single-family homes, including 14 in Windsor Hill Reserve, and no townhomes. Homes were built mostly from 1989 to 2002, with Reserve homes from 2006 to 2015. They range from about 2,380 to 9,680 square feet on lots of about 0.5 to 2.5 acres, according to Orange County Property Appraiser records. MLS listings show 4 to 5 bedrooms.
How much do homes cost in Windsor Hill?
Over the past two years (MLS data, October 2026), homes in Windsor Hill sold six times for a median of about $995,000, ranging from about $900,000 to $1.25 million. For today's listings, see the top of this page.
What are the HOA fees in Windsor Hill?
Recent MLS listings show HOA dues of about $101 to $111 per month 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 Windsor Hill, but check the property tax bill for any special assessments. The association is Windsor Hill Homeowners Association, Inc., which covers Windsor Hill Reserve too.
What schools serve Windsor Hill?
Orange County Public Schools' 2026-27 school zones place Windsor Hill in Thornebrooke Elementary, Gotha Middle and Olympia 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.
Is Windsor Hill in Windermere the same as Windsor Hills?
No. Windsor Hills is a resort community in the Kissimmee and Four Corners area. Windsor Hill is the Windermere community of 109 homes off Windy Ridge Road, including Windsor Hill Reserve, with its own association. The short private streets of nearby Hempel Cove and Porto Lago are not part of Windsor Hill.
Can you rent homes in Windsor Hill short term?
No Windsor Hill-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.
