Windsor at Westside HOA and CDD fees

Homes in Windsor at Westside (Kissimmee) pay a median $7,044 a year in HOA dues, about $587 a month, based on 101 listings. Half fall between $6,758 and $7,280.

Yes, most homes. 88% of the 98 listings with a known CDD status report one, and 85 gave an amount: a median $1,922 a year (range $1,080 to $3,214). Listings are a sample, not the district's records, so check the tax bill for the exact home. The CDD is billed on the property tax bill, not by the HOA. Part of it usually pays down bonds that end on a set date, while the operations part continues.

HOA, CDD and property tax come to about $1,485 a month at the medians (property tax median $8,850 a year). Insurance and the mortgage come on top. Property tax resets after a sale under Florida's homestead rules, so a buyer's bill can be higher than the seller's.

Stellar MLS via Repliers listings in Windsor at Westside from January 2026 to October 2026: homes for sale now plus closed sales in that period, one data point per address (rentals excluded). Fees are converted to annual figures. Individual homes vary by association and home type, so confirm the exact fee on any home before you make an offer.