The newest of the five Windsor resorts — a gated Pulte community in Lake County's Four Corners area, purpose-built for short-term rental, with homes up to 10 bedrooms and a 16,000+ sq ft clubhouse that opened in June 2025. A lot of what's published about this resort is recycled from its sister communities; this page is built from the HOA's and CDD's own documents, with every estimate labeled.
Windsor Cay is the fifth resort in the Windsor family (after Windsor Palms, Windsor Hills, Windsor at Westside, and Windsor Island) and the only one where the builder is still active. Homes started delivering around 2023–24, and the resort's centerpiece — The Reef Club, a 16,000+ sq ft clubhouse with dual water slides, a lazy river, and three food-and-drink outlets — opened in June 2025. Everything below is what that actually means for an owner's wallet.
2023-and-later construction means modern layouts, current building code, and builder-warranty coverage — a real difference from 2005-era Windsor Hills when you're budgeting maintenance and furnishing for rental duty.
Windsor Island and Windsor Hills are resale-only. At Windsor Cay, Pulte was still selling as of August 2026, with quick move-in homes and a 5-bedroom townhome entry point in the low $500Ks — you can buy new here, not just used.
16,000+ sq ft clubhouse, zero-entry pool with dual water slides, lazy river, splash pad, mini golf, arcade, fitness center, and on-site dining — all open and operating since June 2025. No "amenities coming soon" risk left.
Its Windsor siblings sit in Polk and Osceola. Windsor Cay's Lake County address means an 11% combined lodging tax (lowest of the three counties), Airbnb collecting the county tax, and no county business tax at all.
Homes run 5 to 10 bedrooms — the large-group product that dominates this corridor's demand. Dues bundle lawn care, daily valet trash, cable, and internet, and townhome dues even cover repainting and re-roofing.
It's ~9 miles to Disney — farthest of the "close" Windsors (Windsor Hills is ~2.5). The HOA is young with a short operating history, CDD debt runs to roughly 2055, and you'll compete with the builder and a wave of brand-new listings. Details below.
As of August 2026, Windsor Cay HOA dues are quoted at roughly $475–$600 per month depending on floor plan (realtor-published figures — verify with the association, Castle Group), plus an official FY2026 CDD assessment of about $1,275–$2,599 per year on the tax bill and a one-time capital contribution of about $3,000 at closing.
Sources: Windsor Cay CDD adopted FY2026 budget (official) for CDD figures; Castle Group / HOA sites for management and inclusions; realtor-published ranges (2025) for dues, capital contribution, and pricing — dues figures are unverified against an HOA budget, so confirm with the association. A rule of thumb circulating locally puts property taxes + CDD near 1.6% of purchase price per year (estimate only). Compare these costs across all 15 corridor resorts in our Resort Cost Index.
One accuracy note, because plenty of listing sites get it wrong: Windsor Cay's clubhouse is The Reef Club — the "Aloha Clubhouse" you'll see on some pages is recycled Windsor Island copy. Everything below is built and operating per the HOA's own amenities page.
Amenity list from the Windsor Cay Resort HOA's official amenities page (checked Aug 2026). Hours: The Reef Club daily 8 AM–8 PM; pool and water amenities 10 AM–7 PM.
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Two Castaway townhome variants plus seven single-family plans. Base prices below are Pulte's as of August 16, 2026 (via aggregator data — confirm current pricing and availability at pulte.com).
The entry point to the resort — a 5-bedroom, 4.5-bath townhome and the lowest-priced way into new construction at Windsor Cay.
Same 5-bedroom layout with the extra light and privacy of an end position — a modest premium over the interior unit.
The smallest detached plan — a 5-bedroom single-family for buyers who want a private pool home rather than a townhome at the same bedroom count.
A two-story single-family plan between the Winstone and Lakeshore in Pulte's lineup. Its bed/bath count and pricing weren't captured in our verification pass — confirm current specs at pulte.com.
A 5-bedroom with a bath for every bedroom — the ensuite-heavy configuration large-group guests pay up for.
The step into true big-group territory: 7 bedrooms across 3,286 sq ft, targeting the multi-family reunion bookings this corridor runs on.
An 8-bedroom over 4,000 sq ft — estate-class capacity without the flagship price tag.
The 9-bedroom step between Baymont and the flagship. Base pricing wasn't captured at verification — confirm with Pulte.
The flagship: 10 bedrooms and 8 baths, with built-out examples listed to roughly $1.59M. The largest rental product in the Windsor family.
Floor plans courtesy of Pulte Homes; Clearwater, Clearwater Grand & Seashore sheets via WindsorCayFlorida.com. Specs and base prices from Pulte plan data as of Aug 16, 2026 — verify current figures at pulte.com.
Straight talk: no public dataset isolates Windsor Cay itself — the resort is too new. The honest way to underwrite it is the surrounding market data (Clermont and Four Corners, where most listings are already 5+ bedroom homes like these) plus clearly-labeled realtor projections. Here's both, labeled.
Sources: AirROI Clermont and Four Corners market data (TTM Aug 2025–Jul 2026), AirDNA Clermont (through mid-2026), and realtor-published projections (labeled as marketing). Estimates only — results vary by bedroom count, furnishing, pricing, and management. Peak month is March; September is the trough.
Market averages only tell half the story. Our free community guide includes real numbers from self-managing owners and property managers who run units inside Windsor Cay.
Windsor Cay sits in Lake County — a different (and simpler) jurisdiction than its Polk and Osceola siblings. Renting short-term is fully legal; the county has no STR-specific ordinance and no business tax. Our sister company handles all of this for owners.
Every community has trade-offs — and in a resort this new, the record is short. These are the ones buyers should price in, and sellers should be ready to talk about.
Pre-construction-era pages quoted ≈$390–$410/month; 2025 sources cluster at $475–$600. That's a big move from what early buyers were told, and the association has never published an official dues schedule. Get the actual figure for your specific product from Castle Group or the estoppel before you underwrite anything.
The FY2026 assessment is real money — ≈$1,275/yr on a townhome up to ≈$2,599 on a 50-foot lot, on top of HOA dues — and the Series 2024 bonds amortize for about three more decades. Combined property taxes + CDD tend to land near 1.6% of purchase price per year (rule-of-thumb estimate). It's a known, budgetable cost; just make sure it's actually in your budget.
Occupancy is capped at 90 days per calendar year — sources conflict on whether that's per owner or per guest, so verify the recorded CC&Rs. Either way: no living here, no snowbird season beyond 90 days, no pivot to a 6-month tenant if the STR market softens. This is a pure short-term rental asset.
The community only started delivering homes around 2023–24, and early owners ran roughly 1.5–2 years before The Reef Club opened in June 2025 — a real drag on early rental performance that shows up in some resale histories. Budgets, reserves, and amenity operating costs have only a couple of cycles behind them, so review what history exists closely.
Resale 5-bedrooms were asking $620K–$685K in August 2026 while Pulte's comparable new Castaway started at $522,990 — a resale buyer must value the furniture, reviews, and bookings to bridge that gap. On the rental side, Airbnb search shows heavy "brand new" listing density inside the resort, so a generic listing gets buried. Sellers here win on documented revenue.
Realtor projections for Windsor Cay claim 62–67% occupancy. The measured market runs 41–49% (AirROI, Four Corners/Clermont TTM) to 59% on AirDNA's basis. Top-quartile operators do beat the market — but underwrite at market numbers and let outperformance be upside, not the plan.
Compiled from the CDD's adopted budget, HOA publications, realtor and management-company data, and market datasets — Windsor Cay–specific owner discourse is thin because the resort is so new. Always verify current association budgets and disclosures during your inspection period — we can help you request them.
Windsor Cay sits off US-27 just south of the US-192 intersection at 16100 Windsor Cay Blvd. The site plan below shows the lot layout by product — 25-foot townhome rows and 40- and 50-foot single-family lots — with The Reef Club amenity campus near the entrance.
Community map courtesy of Pulte Homes via Jerry Barker Group (lot map dated July 2026 — lot availability changes; confirm with Pulte).
Buying, not selling?
This guide covers what Windsor Cay is — the amenities, the floor plans, what it is like inside the gates. If what you need is whether the purchase works, John keeps a buyer’s breakdown on his agent site: HOA and CDD with their sources, the leasing rule, what to verify before you offer, and the calculator preloaded with this community’s figures.
See the Windsor Cay buyer’s breakdown →johnandrewhomes.com · Johnathon Candelario, Preferred SHORE
Whether you're weighing new construction against a furnished resale or deciding if it's time to sell, talk to a team that works this corridor every week — and reads the actual budgets.
For additional information regarding purchasing a home at Windsor Cay Resort, contact John at 407-750-2434 or contact us here.
If you own a home at Windsor Cay Resort and are considering selling or have questions about the sales process, contact us here to find out how your home would benefit as a featured listing.
Must-have information for owners and prospective owners — HOA details, real rental projections and historicals from owners and managers in the community, and what to check before you buy.
Tell us how to reach you and we'll send the current list of available Windsor Cay homes — new construction and resale — plus honest guidance on which floor plans rent best.
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