| HOA dues | ≈$542–$727 / monthCondo sub-association dues have risen sharply since 2023. Confirm the current schedule for the specific product type.2025 association schedule, all-in by product, via VHG Resort Cost Index · verified Aug 2026 |
|---|---|
| CDD assessment | NoneNo Community Development District assessment on the tax bill here, which is a genuine cost advantage over the newer Polk-side communities.County tax roll, via VHG Resort Cost Index · verified Aug 2026 |
| Minimum lease term | No HOA-imposed minimumNo front-desk or on-site-program requirement either — you can use any manager, or self-manage.Community governing documents, via VHG community research · verified Aug 2026 |
| Short-term rental position | Permitted community-wideThe whole community is short-term-rental zoned; it is what it was built for.County zoning and association documents, via VHG community research · verified Aug 2026 |
| Combined lodging tax | 13.5% combined6% state + 1.5% surtax + 6% tourist development tax. Osceola has no platform agreement for the TDT portion — owners self-remit monthly.Osceola County Tax Collector + Florida DOR · verified Aug 2026 |
| Nightly rate (market proxy) | $110–$400+ / night by sizeUnconfirmed — verify with the association2BR condos $110–$160 · 3BR $130–$200 · 4BR homes $180–$260 · 5–6BR villas $250–$400+.Agent estimates published March 2026 · Mar 2026 |
| Occupancy (market proxy) | 55–70%Unconfirmed — verify with the associationResort-marketing sources claim 65–78%. Treat anything above the mid 50s as optimistic until you have seen owner statements.Conservative underwriting range; Kissimmee market spans 45–69% across vendors · mid-2026 |
Windsor Hills sells on proximity, and the proximity is real — roughly two miles to the Walt Disney World gates, which is closer than most of the corridor and shows up directly in both nightly rate and occupancy. For a guest choosing between a twenty-minute drive and a five-minute one, that is the whole decision.
Financially, the standout feature is what is not on the tax bill. There is no CDD assessment here, which in a corridor where districts routinely add $1,300 to $4,600 a year is a material and permanent cost advantage. It is the single clearest argument for the older Osceola communities over the newer Polk-side developments.
The counterweights are age and dues. The housing stock is older than ChampionsGate or Solara, so roof and AC life belongs in your underwriting rather than in the optimism column. And the condo sub-association dues have moved up sharply since 2023 — the all-in figure by product is the one to ask for, not the headline number in a listing.
Figures are current as of the dates shown and change. Confirm the current dues schedule for the specific product type and the leasing article of the recorded declaration before you rely on them. Rate and occupancy figures are estimates and market proxies, not measured community performance.