A gated, Pulte-built short-term rental resort in Four Corners — newer homes (2015–2020), a lazy-river pool complex with the Tu Casa bar, and single-family houses up to 9 bedrooms. It's roughly 6–7.5 miles to Disney, and it carries a CDD assessment on the tax bill — here's the full picture: real costs, real rules, and realistic rental numbers.
Windsor at Westside is one of the newest of the Pulte-built "Windsor" resorts — 612 homes on about 160 acres, built out between 2015 and 2020, every one with a private pool. The 10,000 sq ft clubhouse anchors a genuinely photogenic amenity core: zero-entry pool, double waterslide, lazy river, splash playground, and the Tu Casa poolside bar with a full food-and-liquor menu.
The whole community is a decade old or less — modern layouts, newer roofs and systems, and lower near-term capex than the early-2000s resorts on the same corridor.
Townhomes run 4–5 bedrooms and single-family homes go up to 9BR / ~4,391 sq ft — the very-large-group product that older resorts like Windsor Hills simply don't have, and the segment with the highest gross revenue per booking.
Zero-entry pool, double waterslide, lazy river, hot tub, and a kids' water playground. In guest forums, the pool complex is consistently the number-one reason people book here.
A poolside tiki-style bar with a full liquor bar, food menu, and online ordering — an on-site food-and-drink amenity most corridor communities can't put in their listing photos.
Landscaping and irrigation, bulk Spectrum internet + cable, daily valet trash, the staffed gate, and every resort amenity ride on one HOA payment — fewer utility bills and vendor headaches per home.
It's roughly 6–7.5 miles to Disney — farther than Windsor Hills — and there's a CDD assessment of roughly $1,900–$2,900 a year on the tax bill. Neither is a dealbreaker, but both belong in your math from day one.
As of August 2026, Windsor at Westside's official FY2027 CDD assessment is $1,922–$2,910 per year depending on lot type, while current HOA dues are genuinely unverified — the $390–$410/month figures still circulating on realtor sites are undated builder-era numbers, and live MLS data shows association fees as high as roughly $722/month. Verify the current dues schedule with the association before you write an offer.
Sources: Windsor at Westside CDD FY2027 adopted budget (Aug 2026, official) for CDD figures; official HOA TownSq site for management and inclusions; realtor/aggregator listing data (Aug 2026) for prices and the dues discrepancy. HOA dues are flagged unverified — confirm with Castle Group. Compare these costs across all 15 corridor resorts in our Resort Cost Index.
Amenity list and hours from the resort's official site, windsoratwestside.com (accessed Aug 2026). Realtor sources also mention a multi-sports court, soccer field, and tennis/pickleball — the courts list varies by source, so verify specific courts on a visit. Hours change seasonally — see FAQ below.
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Every home at Windsor at Westside has its own private pool. Townhomes run about 2,102–2,263 sq ft; single-family homes range from roughly 2,490 to 4,391 sq ft. The signature Pulte models:
The flagship — nine bedrooms for the very largest groups. This is the product tier older Windsor resorts don't offer, and the top of the community's revenue-per-booking range.
Big-group workhorse: eight bedrooms and six baths with the square footage to sleep multi-family parties comfortably.
Seven bedrooms with two owner's suites — a layout guests specifically search for when two families travel together.
The mid-size single-family plan — six bedrooms in a footprint that balances purchase price against group capacity.
The community's entry point — 4–5 bedroom townhomes, each with a private pool. View full townhome brochure (PDF)
Floor plans courtesy of Pulte Homes via Realty In Orlando.
Straight talk: nobody publishes Windsor at Westside–specific performance data. The best available proxies are ZIP 34747 (the resort's ZIP) and Kissimmee-market figures — and because this community is exclusively 4–9 bedroom homes, market-wide averages understate what its typical listing grosses. These are the labeled ranges, not promises.
Sources: Chalet ZIP-34747 data (2025); AirROI and AirDNA Kissimmee market data (through mid-2026); FunStay Florida published projections (promotional). All figures are proxies — no public dataset covers this resort specifically. Results vary widely by home size, condition, 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 at Westside.
Windsor at Westside sits in unincorporated Osceola County. Renting short-term is fully legal — you just need the right registrations, and one Osceola-specific catch: the county's 6% tourist tax is never collected by Airbnb or Vrbo, so every owner self-files it monthly. 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.
Every home carries a Community Development District assessment on its Osceola tax bill: about $1,922/yr for townhomes, $2,307 for 40' lots, and $2,910 for 50' lots (FY2027, official). The operations portion jumped roughly 65% in FY2025 — townhomes went from $661 to $1,093 — driven mainly by reclaimed irrigation water costs rising from a $150,000 budget to a $405,900 line item. It has held flat since, but the episode shows how fast a CDD line can move. Bond debt amortizes into the 2040s.
Realtor sites still quote $390–$410/month, but those numbers are undated builder-era figures — and current MLS data shows association fees on listings as high as roughly $722/month. That's potentially a $3,700+/yr difference in your underwriting. Get the current dues schedule and budget in writing from Castle Group (407-507-1417) before you make an offer; we can help you request them.
Roughly 98 of the community's 612 homes were listed for sale at once in August 2026 — about 16% of the resort. For buyers, that's real leverage. For sellers, pricing and presentation decide everything, which is exactly where real rental numbers and a featured listing earn their keep.
At 6–7.5 miles from Disney, Windsor at Westside loses some guests to closer resorts — guest forums show travelers filtering it out on distance alone. Winning listings sell the lazy river, Tu Casa, and the newer homes instead of proximity. If your target guest is "closest to the parks at any price," this isn't their community.
Guest forums describe reviews across the resort as inconsistent — individual home condition varies widely, and some travelers cite noise from large groups and perceptions of lax security. The resort runs a roving patrol from 4 PM to 8 AM, but your reviews will be driven by your home's condition and management, not the gate. Budget for furnishing quality and real guest support.
Unlike some Florida counties, Osceola has no collection agreement with Airbnb or Vrbo — the 6% TDT must be self-remitted monthly by the owner or agent on every booking, with returns due even in $0 months. Miss filings and penalties stack. It's simple once set up, but it's a recurring obligation many out-of-state buyers don't expect.
Compiled from official CDD budgets, county sources, owner and guest discussions, and listing data. Always verify current association budgets, CDD assessments, and disclosures during your inspection period — we can help you request them.
The clubhouse, lazy-river pool complex, and Tu Casa sit at the community's amenity core on Tripoli Court, off Westside Blvd. Guest gates are assigned by street — Tripoli Court, Lima Ave, and Sydney Ave — with townhomes and single-family streets radiating around the amenity center.
Community map courtesy of Pulte Homes via Team Donovan.
Buying, not selling?
This guide covers what Windsor at Westside 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 at Westside buyer’s breakdown →johnandrewhomes.com · Johnathon Candelario, Preferred SHORE
Whether you're buying your first vacation home 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 home at Windsor at Westside Resort, contact John at 407-750-2434 or contact us here.
If you own a home at Windsor at Westside 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 and CDD 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 at Westside homes, plus honest guidance on which floor plans and home sizes rent best.
We'll walk you through what your home is worth today, how a featured listing works, and your options — including an offer from our investor network if you want speed.
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