| HOA dues | Not published — MLS shows up to ≈$722 / monthUnconfirmed — verify with the associationStale $390–$410 quotes persist all over the internet while MLS entries show up to roughly $722. Do not offer on this community without the current schedule in hand from the association.MLS observation; no primary schedule located, via VHG Resort Cost Index · verified Aug 2026 |
|---|---|
| CDD assessment | $1,922–$2,910 / yearThe operations and maintenance half jumped roughly 65% in FY2025. That portion never ends and is reset annually.FY2027 adopted district budget, via VHG Resort Cost Index · FY2027 budget |
| Minimum lease term | No resort-imposed minimum foundUnconfirmed — verify with the associationManagers typically set their own 2–3 night minimums as business policy rather than by rule.Public sources, via VHG community research · verified Aug 2026 |
| Short-term rental position | Permitted — purpose-built for itOsceola zoning + association documents · verified Aug 2026 |
| Combined lodging tax | 13.5% combinedOsceola County Tax Collector + Florida DOR · verified Aug 2026 |
| Nightly rate (market proxy) | ≈$237–$290 / night (proxy)Unconfirmed — verify with the associationLarger homes run higher. Market-level proxy.ZIP 34747 ≈$237; Kissimmee market $281–$290 · mid-2026 |
| Occupancy (market proxy) | ≈45–56%Unconfirmed — verify with the associationSupply growing fast — one provider shows +53.7% listings year on year, which pressures pricing.ZIP 34747 ≈52%; Kissimmee market 44.8–56% by provider · mid-2026 |
Windsor at Westside is a capable purpose-built resort community with a real problem for buyers: you cannot easily find out what it costs to own. The association’s current dues schedule is not published anywhere reliable, stale figures of $390 to $410 a month persist across listing sites, and MLS entries show amounts up to roughly $722. Those are not small discrepancies.
The district assessment is better documented and less comfortable. The FY2027 adopted budget puts it at $1,922 to $2,910 a year, and the operations and maintenance half rose roughly 65% in FY2025. That is the portion that never ends, and it is reset every year by the district board.
None of this makes it a bad community. It makes it one where the ordinary shortcut — trusting the listing — is more likely to be wrong than anywhere else in this guide. Get the current schedule in writing, and treat any number you find online as a starting question.
The HOA figure here could not be confirmed from any primary source and published figures conflict materially. Do not rely on any number for this community without the association’s current schedule in hand.