The closest guard-gated short-term rental resort to Walt Disney World — 999 condos, townhomes, and pool homes built out between 2004 and 2010, with a water park, no CDD, and dues that cover more than most. It's a mature community with a real track record, which also means real numbers to scrutinize: here are the costs, rules, and rental performance as we actually found them.
Windsor Hills' pitch fits in one sentence: no other guard-gated short-term rental resort sits this close to Disney. Everything else about the community — the 999-unit scale, the mature comp set, the amenity package, the absence of a CDD — supports that headline rather than replacing it.
Less than 2 miles from Walt Disney World — roughly 5–10 minutes by car to the gates. For guests picking on a map, that proximity wins bookings before your photos even load.
Unlike ChampionsGate, Reunion, Windsor at Westside, or Windsor Island, there's no CDD bond on the tax bill here — a saving one local source pegs at "thousands less per year" versus newer master plans. Verify on any specific property's tax bill.
All 999 units — 320 condos, 210 townhomes, 469 single-family homes — were delivered in the 2004–2010 buildout. No construction noise, an established comp set, and years of rental history to underwrite against. The flip side: 2000s-era homes need renovation budgets, and buyers will compare yours to freshly themed newer resorts.
Master dues include basic cable/internet, 24-hour guard-gated security, and all amenities. Single-family dues add lawn care and daily doorstep trash; townhome dues add roof replacement and exterior paint; condo dues add water and building insurance. That simplifies remote ownership — but it isn't cheap, as the costs section shows.
Amenities — pool, water park, theater, courts — are free to registered guests with a wristband. No daily amenity fee, no parking fee. That's a genuine listing-page edge against resorts that tack fees onto every stay.
The AquaVenture water park was added in 2018, and its slides were fully replaced in a January–February 2026 capital project. Reinvestment is a good sign for a 20-year-old community — though it also means occasional amenity downtime, and the project's funding source wasn't disclosed.
As of August 2026, Windsor Hills' most recent published dues schedule (2025) puts the master association at $1,117.97 per quarter for every owner, plus a sub-association add-on by product type — roughly $543/month all-in for a single-family home, $542 for a townhome, and $619–$727 for a condo — with no CDD on top. No 2026 schedule has been published; verify current amounts with the association before you write an offer.
Sources: 2025 dues schedule as published on a Windsor Hills buyer's guide (verified 8/16/26; the condo sub-association figure conflicts between $737.90 and $1,061.84 — verify with the association at 407-787-4255 before relying on it); live IDX listing data and a 2026 agent market guide for prices. Beware stale figures still circulating online ($898/qtr all-in is years out of date). Compare these costs across all 15 corridor resorts in our Resort Cost Index.
Amenity list compiled from the community's own site and current resort information pages (2026). Pool 8am–10pm; water park 10am–8pm; fitness center 6:30am–10pm; grill 10am–8pm — hours subject to change, see FAQ below.
Subscribe for your free community guide that has must-have information for owners and prospective owners — including real projections and historicals from self-managing owners and property managers who run units in Windsor Hills.
Windsor Hills was delivered by its original developer in three products: Ventura-building condos, Vistas townhomes, and Enclave single-family pool villas. Community-wide, properties run from about 1,081 sq ft (2BR condos) up to roughly 2,832–3,232 sq ft, with 2 to 7 bedrooms. Here are nine of the original plans:
The big-group plan — six bedrooms put it in the resort's top rental tier, where the largest gross revenues (and the largest operating budgets) live.
Five ensuite-heavy bedrooms — a bathroom count that photographs well on listing sites and suits multi-family groups.
The alternate five-bedroom layout — same headline count as the Seville with a different room arrangement.
One of the original single-family villa plans — confirm bedroom count and square footage against the specific listing you're evaluating.
One of the Ventura-building condo layouts. Condos at Windsor Hills run 2BR/2BA (from ≈ 1,081 sq ft) to 3BR/2BA (≈ 1,410 sq ft).
Ventura-building condo layout — verify the bedroom count and square footage on the individual listing.
Ventura-building condo layout — verify the bedroom count and square footage on the individual listing.
Ventura-building condo layout — verify the bedroom count and square footage on the individual listing.
Ventura-building condo layout — verify the bedroom count and square footage on the individual listing.
Floor plans courtesy of the community's Pulte-era developer via Jerry Barker, Realtor. A Saddlebrook 3BR/3BA townhome plan also exists but isn't shown here. Plans are historical developer drawings — confirm dimensions against the specific property.
Straight talk: there is no audited, resort-specific dataset for Windsor Hills. The figures below are agent-published estimates and market proxies — and the vendors disagree with each other on occupancy by more than 20 points. Treat these as underwriting ranges, not promises, and remember the “Kissimmee average” blends $28K condos with $90K six-bedroom villas.
Sources: 2026 agent market guides (methodology undisclosed), an AirDNA-derived third-party citation, and Kissimmee-market reports (AirROI, trailing twelve months to Jul 2026). Estimates only — results vary by size, condition, pricing, and management.
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 Hills.
Windsor Hills sits in Osceola County's short-term rental corridor with a Kissimmee mailing address. Renting short-term is fully legal — you just need the right registrations, and one Osceola quirk trips up more owners than any other: the county's 6% tourist tax is never collected by Airbnb or Vrbo. Our sister company handles all of this for owners.
Every community has trade-offs. These are the ones buyers should price in — and sellers should be ready to talk about.
The Ventura condo sub-association fee was $616.35/qtr in 2023; the same buyer's-guide source has shown both $737.90 and $1,061.84/qtr labeled as 2025. At the higher figure, a condo's all-in dues approach $727/month. The fee explicitly includes building insurance — the cost line that's been escalating across Florida condos. Get the current budget in writing from the association (407-787-4255) before you write an offer.
The master fee went from $980.86/qtr (2023) to $1,117.97/qtr (2025), and no 2026 schedule is published. Meanwhile, agent sites still advertise "one of the lowest HOA fees in the area, just $898 per quarter" — a total that's years out of date. If a listing's quoted dues look low, they probably are.
No parking on any resort road, sidewalk, or grass — violators are towed at the driver's expense, and enforcement is real. Practical capacity is about 2–3 vehicles per rental, with an overflow lot by the tennis courts. If your target guest is the 12-person, four-car reunion group, plan around this before you buy a 6-bedroom.
There's no curbside pickup: 13-gallon bags go inside the bench box at the front door early in the morning, with compactors for overflow. It's a genuine amenity (single-family dues include daily removal), but guests who pile bags outside or leave an overflowing bin at checkout can trigger extra removal charges. Build it into your house manual.
Active inventory grew from roughly 30–35 listings in 2023 to 45–50 by early 2026, and days-on-market stretched from about 60 to 110–120. Zip-level price per square foot is down ≈ 8% year-over-year. For buyers that's leverage; for sellers, pricing and presentation decide everything.
The water park closed January 5 – February 13, 2026 for slide replacement (the main pool stayed open), and guest reviews periodically report the grill or pool bar closed during their stay. Reinvestment is the good news; just don't write listing copy that guarantees every amenity every day, and note the project's funding source (reserves vs. assessment) wasn't disclosed.
Compiled from association-published dues schedules, county records, listing data, and guest reviews. No recent special assessment or governance dispute surfaced in our research — but that's absence of evidence, not proof: always review the budget, reserve information, and estoppel during your inspection period. We can help you request them.
The main entrance is off North Old Lake Wilson Rd, with the clubhouse, lagoon pool, and AquaVenture water park at the community's core. Condo buildings cluster near the amenity center; townhome streets ring it; single-family villas fill the outer loops. Trash compactors sit at Comrow St & Almaton Loop, the Dinville St playground, Archfeld & Teascone Blvd, and the recreation-area lot.
Community map courtesy of Magical Stays.
Buying, not selling?
This guide covers what Windsor Hills 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 Hills buyer’s breakdown →johnandrewhomes.com · Johnathon Candelario, Preferred SHORE
Whether you're buying your first vacation rental or deciding if it's time to sell, talk to a team that operates short-term rentals across this corridor every week.
For additional information regarding purchasing a property at Windsor Hills Resort, contact John at 407-750-2434 or contact us here.
If you own a property at Windsor Hills Resort and are considering selling or have questions about the sales process, contact us here to find out how your property would benefit as a featured listing.
Must-have information for owners and prospective owners — HOA details by product type, 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 Hills condos, townhomes, and pool homes, plus honest guidance on which products and plans rent best.
We'll walk you through what your property is worth today, how a featured listing works, and your options — including an offer from our investor network if you want speed.
Check your inbox — and if it's urgent, call John directly at 407-750-2434.
