Every listing sheet for Windsor Cay quotes the same range: an HOA fee somewhere between $485 and $600 a month, a Community Development District assessment estimated at $1,800 to $2,400 a year, and a one-time $3,000 capital contribution due at closing. Those numbers show up on the builder's page, the property manager's page, and every agent flyer built around them. What none of those sheets say plainly is that the number is a snapshot of a community that isn't finished being built yet, and the fee an owner pays in year four looks different from the fee quoted today.
That gap matters more here than in most Central Florida resort communities, because Windsor Cay is doing two things at once that its sibling properties aren't. It's still mid-construction, with Pulte releasing roughly 800 planned homes in phases and offering a $6,000 HOA credit to phase-one buyers who pay cash or finance through an approved lender. And it sits in Lake County, in the city of Clermont, rather than the Osceola County corridor where most of its Pulte-built peers, Windsor Island, Windsor Hills, and Windsor at Westside, already operate. Both facts change the math an investor should run before signing.
The fee you're quoted is a phase, not a steady state
New-construction HOAs price their dues against total planned overhead, then divide by the number of homes currently paying in. When a builder still owns unsold lots and unbuilt phases, it typically covers or subsidizes the gap so early buyers see an attractive, competitive number. Windsor Cay's HOA has been set, by the builder's own comparison, to land in line with what Windsor Island Resort already charges, a community that finished construction in 2024. That's a reasonable benchmark for what a mature, fully built Windsor-brand resort costs to run. It is not necessarily what Windsor Cay itself will cost once every phase closes and the developer turns association control over to homeowners.
The $6,000 HOA credit offered to phase-one buyers is itself a signal worth reading. Builders don't subsidize dues on properties they expect to hold value on fee structure alone. The credit exists because the fee, at this stage of build-out, needs help looking competitive against finished communities nearby.
Where the numbers sit today
| Cost component | Reported range | Timing |
|---|---|---|
| Monthly HOA | $485–$600 (some listings show $450–$600 for townhomes) | Current, phase-based |
| CDD assessment | $1,800–$2,400 per year | Estimated, varies by home series |
| One-time HOA capital contribution | $3,000 | Due at closing |
| Builder HOA credit | $6,000 | Phase-one buyers, cash or approved lender only |
| Total property tax including CDD | Approximately 1.6% of purchase price | Ongoing |
These figures come from the builder's own materials and the community association's published guidance, and every source that quotes them adds the same caveat: verify the current number before writing an offer, because community fees adjust over time. That caveat is doing more work than it looks like at first read. It's an admission that the number on today's sheet is not a contract term, it's a marketing estimate tied to a specific construction phase.
The CDD line nobody reads twice
A Community Development District assessment has two parts that behave differently, and the difference is the part investors tend to skip past. One portion is the bond assessment, the fixed payment that retires the debt the district issued to build roads, utilities, and shared infrastructure. That number doesn't move once it's set. The other portion is the operations and maintenance assessment, which covers the ongoing cost of running the clubhouse, the pool, the landscaping, and every amenity the resort markets to renters. O&M assessments are reviewed annually and typically climb a few percentage points a year as materials, labor, and insurance costs rise, independent of anything the bond portion does.
For an investor modeling ten years of cash flow on a $700,000 vacation home, the difference between a flat number and a compounding one is not trivial. A CDD line that reads $2,000 a year at closing can be meaningfully higher by year five purely from O&M creep, with no change to the bond obligation at all.
A county that hasn't done this before
Windsor Cay is described in builder materials as the first major resort-style vacation home community in Lake County. That distinction sounds like a marketing footnote until an investor tries to get a short-term rental license.
Most buyers in this category have experience, or have talked to people with experience, in the Kissimmee and Four Corners corridor, where Osceola County's short-term rental licensing process is well established and unincorporated resort communities operate under a county framework that's been tested for years. Windsor Cay doesn't sit there. It sits inside the city limits of Clermont, in Lake County, which means the licensing path runs through Clermont's own municipal process rather than the Osceola County pipeline most STR property managers already know by heart.
The city of Clermont's vacation rental page lays out what that means in practice. An owner needs a Florida DBPR license, a Department of Revenue registration for sales tax reporting even when a booking platform collects and remits, and a separate $375 city vacation rental fee. On top of the paperwork, the application requires a building permit specifically for a life-safety inspection, complete with an interior sketch showing every room, staircase, smoke and carbon monoxide detector, fire extinguisher, and exit sign. That's a materially different intake process than a buyer coming from an established Osceola resort would expect, and it's not the kind of detail that shows up in a builder's amenity brochure.
At the county level, Lake County's own short-term rental ordinance sets an initial license fee of $95, renewed annually at $95, with a $190 fee for anyone found operating without one first. That's a lighter administrative footprint than what's grown up around the mature Kissimmee corridor, but light-touch and untested aren't the same thing. A county building its first significant concentration of resort-style rentals is also a county without years of enforcement precedent behind it, which is a different kind of risk than the one investors are used to pricing in Osceola.
The rules that don't make the brochure
Two operational details worth knowing before closing rarely appear on the glossy pages. Windsor Cay's HOA caps occupancy at 90 days per guest per year, a limit that shapes how a longer-stay or repeat-guest rental strategy can be structured. And the association restricts converting garage space into a game room, a common revenue-adding renovation at older Four Corners resorts, though every home comes with loft space that can serve the same purpose. Neither rule changes the investment case on its own, but both are the kind of fine print that separates a buyer who read the HOA documents from one who read the amenity list.
The amenities themselves are real and well documented. The Reef Club clubhouse anchors the community with a zero-entry pool, a lazy river, a kids' splash zone, a 9-hole mini golf course, and on-site dining at Blue Lagoon Bar & Grille, with a poolside tiki bar called Rumbrellas and a quick-service stop, Breeze Canteen, for ice cream and cold drinks between pool sessions. Those amenities are what drive rental demand and guest reviews. They're also exactly what the HOA fee is paying to maintain, which is why the fee's trajectory matters as much as its current number.
A few questions worth asking before you sign
Is Windsor Cay zoned for short-term rental? Yes. It's marketed and built specifically as a short-term rental community, distinct from a standard residential subdivision, and the HOA structure assumes STR use.
Will the HOA fee stay in the $485 to $600 range after the developer leaves? There's no guarantee it will. The fee is currently benchmarked to a finished sibling community, Windsor Island, and supported by a builder credit available only to phase-one buyers. Ask for the association's current budget and reserve study rather than relying on the range quoted in marketing materials.
Does the Clermont licensing process take longer than Osceola County's? It's a different process, not necessarily a slower one, but it involves a municipal application, a $375 fee, and a life-safety inspection with detailed sketches that an Osceola-based property manager may not already have templates for. Building in extra lead time before a first booking is reasonable.
What's the practical impact of the 90-day occupancy cap? It affects any strategy built around long-stay guests or repeat corporate bookings rather than typical week-long vacation stays. Most short-term rental models built around Disney-area tourism already fall well under that threshold.
The Windsor Cay pitch is a real one. New construction, a builder with a track record at Windsor Island and Windsor at Westside, and an amenity package built for the guest experience that drives strong reviews. The number that gets an investor to the closing table, though, is a number priced for a community that isn't finished yet, sitting in a county that hasn't finished building the regulatory scaffolding around it either. Both of those facts resolve over the next few years. Whether they resolve in the buyer's favor depends on underwriting the fee's trajectory now, not the fee on the sheet.
If you're comparing Windsor Cay against other Central Florida vacation rental communities and want a clearer read on how the fee structure, phase timing, and licensing process actually pencil out for your specific numbers, Andrea Alonso works with investors across this exact corridor and can walk through what the current phase looks like before you commit.
