Windsor at Westside
Windsor at Westside 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 at Westside located?
Windsor at Westside is on the Westside Boulevard corridor in unincorporated Osceola County, with Kissimmee, FL 34747 mailing addresses.
Can you rent homes in Windsor at Westside short term?
Windsor at Westside 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.
What types of homes are in Windsor at Westside?
Windsor at Westside has Pulte vacation homes with 5 to 9 bedrooms and townhomes with 4 to 5 bedrooms, built from 2015 to about 2020, based on MLS listings and sales from the past two years.
How much do homes cost in Windsor at Westside?
Over the past two years (MLS data, October 2026), single-family homes in Windsor at Westside sold for a median of about $585,000, ranging from about $450,000 to $799,000. Townhomes sold for a median of about $405,000. For today's listings, see the top of this page.
What are the HOA fees in Windsor at Westside?
Recent MLS listings show HOA dues of about $550 to $700 per month for single-family homes and about $515 to $665 for townhomes as of October 2026. The resort is in the Windsor at Westside Community Development District, so tax bills include CDD assessments.
What amenities does Windsor at Westside have?
The resort lists a 10,000-square-foot clubhouse with a kids' activity center, Tu Casa Bar & Lounge, game room and gym, plus a resort pool with waterslide, lazy river, hot tub, water playground and basketball.
Who built Windsor at Westside?
Pulte opened Windsor at Westside in 2015. It's one of Pulte's Windsor resorts, along with Windsor Hills, Windsor Island and Windsor Cay.
