The newest of the big Polk County vacation-rental resorts — built by Pulte from 2020 to 2023, with 789 homes from 5-bedroom townhomes to 10-bedroom villas, every one with a private heated pool, wrapped around a water-park-style clubhouse. Here's the full picture: the real dues story, the CDD on the tax bill, the rules that catch people off guard, and what homes actually earn.
Windsor Island is what Pulte built after watching two decades of Disney-corridor resorts: an 8-acre water-park-style amenity campus (the Aloha Clubhouse), a lineup that runs from 5-bedroom townhomes to 10-bedroom villas — all with private heated screened pools — and one all-inclusive HOA bill. Pulte has sold out, so it's now a resale-only community.
Built 2020–2023, with the Aloha Clubhouse opening in late 2021. Roofs, ACs, pool equipment, and appliances are years newer than mid-2000s resorts like Windsor Hills — meaningfully lower near-term capex risk for buyers.
5BR/4BA townhomes (~2,283–2,496 sq ft) up to 10BR/8BA single-family villas (~4,399 sq ft), every home with a private heated screened pool. This is the corridor's purpose-built product for the large-group and multi-family segment.
Zero-entry resort pool, lazy river, dual water slides, kids' splash park, and the Blue Marlin Grille tiki bar — with no resort fees and no wristbands for registered guests. It photographs like a hotel and books like one.
Dues cover the clubhouse, landscaping and irrigation, bulk cable and internet, daily valet trash, and the 24-hour manned gate with roving patrol — no separate club-membership layer like ChampionsGate's Oasis Club.
The Sandmine Road CDD runs about $1,227–$2,374 a year by product — real money, but below ChampionsGate's roughly $3,000 and Solterra's $2,500–$4,000 CDD bills.
It's roughly 9–10 miles to the Disney gates — Windsor Hills is 2–3 — and the resort runs a strict enforcement culture: Proptia guest pre-registration, hard parking caps, and towing. Great for order; it demands a buttoned-up check-in process.
As of August 2026, Windsor Island Resort dues run roughly $550–$600 a month — up about 40% from the $390–$410 presale estimates buyers saw in 2020–21 — and the Sandmine Road CDD adds an official $1,227–$2,374 a year to the tax bill depending on home type. The association publishes no current dues schedule, so verify the exact figure for any specific home with the association before you write an offer.
Sources: Sandmine Road CDD FY2025 adopted budget (official), the association's owner FAQ portal (inclusions), 2026 corridor fee guides, and live listing data (Aug 2026). Exact current dues per product are not published — confirm with the association or a current MLS sheet before relying on them. Compare these costs across all 15 corridor resorts in our Resort Cost Index.
Amenity list from the association's amenities page, the CDD-era Pulte site plan, and the owner FAQ portal. Registered guests get full access with no wristbands or resort fees; cabanas reserve through the front desk. Hours aren't officially published — see FAQ below.
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Every Windsor Island home was built with a private heated screened pool — 12'×24' on the 5–7 bedroom plans and 12'×26' on the 8–10 bedroom plans. The Pulte lineup also included the Seashore (7BR/5.5BA, 3,281 sq ft), Clearwater (9BR/6BA, 4,398 sq ft), and Clearwater Grand (10BR/8BA, 4,383 sq ft) — see the full brochure below. The plans we have staged:
The entry point to the community: a 5-bedroom townhome with its own private pool — the lowest buy-in and the lightest CDD assessment of the three product types.
The compact single-family plan — detached-home privacy and a private pool at close to townhome scale.
Five bedrooms arranged around two owner's suites — a layout built for two families sharing one trip, which is exactly how many groups book.
The mid-size villa: six bedrooms that sleep multi-family groups while staying easier to furnish and turn over than the 8–10 bedroom plans.
The big-group workhorse on a 50' lot: eight bedrooms with the larger 12'×26' pool — the product class that targets peak-week reunion and celebration bookings.
Floor plans courtesy of Pulte Homes via Jerry Barker, Realtor, and Realty In Orlando. View the full all-models brochure (PDF).
Straight talk: no data vendor publishes a Windsor-Island-only dataset, so everything here is a Davenport-market proxy — and that blend mixes small condos with 10-bedroom villas, so it understates what a large, well-run Windsor Island home does. Read the ranges accordingly.
Sources: AirDNA and AirROI Davenport market data (TTM mid-2026), OTA listing rates at the resort (Aug 2026), and property-manager marketing claims (flagged as such). Estimates only — results vary widely by bedroom count, reviews, and management.
Market averages only tell half the story — especially in a community where half the homes have 6+ bedrooms. Our free community guide includes real numbers from owners and managers who run homes inside Windsor Island.
Windsor Island sits in unincorporated Polk County — no city short-term rental license applies. Renting short-term is fully legal; you just need the right registrations. 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.
Buyers in 2020–21 were quoted $390–$410 a month; 2026 estimates put dues around $550–$600 — and the association publishes no official schedule. Don't underwrite off an old listing sheet: confirm the current figure for the specific home with the association before you offer.
The Sandmine Road CDD adds an official $1,227–$2,374 a year on the Polk County tax bill (townhome → 50' home), funding bond debt from three series issued 2020–2022. O&M was held flat FY2024→FY2025 — a good sign — but the debt-service portion runs for the life of the bonds. Per-lot payoff quotes come from the district manager (GMS, 407-841-5524).
Hard vehicle caps that include visitors (5 for 50' homes, 4 for 40' homes, 3 for townhomes), no RVs, and guest reports of overnight tows without notice — including for a partial tire on grass. Put the parking rules in your listing and your check-in message, every time.
Every guest and driver must be pre-registered in the Proptia system, with physical photo ID for everyone 18+, or they're turned away. Guest reviews report 30–45 minute gate backups at peak check-in times (reported partly by a competitor-affiliated site, so weigh it accordingly). A tight registration workflow is part of operating here.
No individual can stay in the community more than 120 days per calendar year — this is a vacation-rental community, not a snowbird one — and one in-resort rental site says stays over 30 nights aren't allowed at all (reconcile with the recorded rules before planning mid-term stays). Also: owners who rent out their homes lose personal amenity privileges.
Depending on the feed, 67–102 of the 789 homes were listed in August 2026 — roughly 8–13% of the community — with average days-on-market near 200 and sales at about 96% of ask (average sold price $654,873 over the 12 months through Feb 2025). Buyers have leverage; sellers need sharp pricing and real rental numbers to stand out.
Compiled from the association's owner FAQ portal, the Sandmine Road CDD budget, listing feeds, and guest reviews (anecdotal items flagged). No special assessments surfaced in our research, but that's absence of evidence, not confirmation — always review the budget, reserve status, and estoppel during your inspection period. We can help you request them.
Windsor Island sits off US-27 at Sand Mine Road, with a single guard-gated entrance. The Aloha Clubhouse campus (1115 Aloha Blvd) anchors the community — the amenity map below keys every feature of the pool deck, and the home-site map shows the lot layout across the townhome, 40', and 50' phases.
Community maps courtesy of Pulte Homes via New Construction Realtor / Winter Garden New Homes.
Buying, not selling?
This guide covers what Windsor Island 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 Island buyer’s breakdown →johnandrewhomes.com · Johnathon Candelario, Preferred SHORE
Whether you're buying your first big vacation villa 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 Island Resort, contact John at 407-750-2434 or contact us here.
If you own a home at Windsor Island 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 Island homes, plus honest guidance on which floor plans and bedroom counts 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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