Windsor Hills Resort
Windsor Hills Resort Living: Local Insights & FAQs
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
Where is Windsor Hills Resort located?
Windsor Hills is at 2600 N Old Lake Wilson Road, just south of US 192 in unincorporated Osceola County, with Kissimmee, FL 34747 mailing addresses.
Can you rent homes in Windsor Hills short term?
Windsor Hills falls inside Osceola County's mapped short-term rental area (the county's Short-Term Rental Boundary). Before buying, confirm the specific property's zoning and the association's rental rules. Owners who rent nightly generally need a Florida vacation rental license and must collect state sales tax and the county tourist development tax. Osceola County's short-term rental subdivision list also names Windsor Hills.
What types of homes are in Windsor Hills?
The resort lists 469 single-family homes, 210 townhomes and 320 condos. Homes have 4 to 6 bedrooms, townhomes 3 bedrooms and condos 2 to 3 bedrooms, based on MLS listings and sales from the past two years.
How much do homes cost in Windsor Hills?
Over the past two years (MLS data, October 2026), single-family homes in Windsor Hills sold for a median of about $625,000, ranging from about $400,000 to $767,000. Townhomes sold for a median of about $395,000 and condos for about $324,000. For today's listings, see the top of this page.
What are the HOA fees in Windsor Hills?
Recent MLS listings show HOA dues of about $505 to $570 per month for single-family homes, about $445 to $575 for townhomes and about $570 to $755 for condos as of October 2026. The master association is Windsor Hills Master Community Association, Inc. No community development district (CDD) turned up in our research; confirm in the resale documents.
What amenities does Windsor Hills have?
The resort lists a clubhouse, pool and water park, movie theater, fitness center, game room, Windsor Marketplace & Grill, a cyber café and a recreation park.
Is Windsor Hills gated?
Yes. The resort describes itself as a 24/7 manned, gated community.
