MLS data updated Jun 26, 2026
Windsor Cay
Guard-Gated Resort Homes Near Disney
Clermont, FL
A guard-gated resort community near Clermont and the Disney area, zoned for short-term rental, offering large pool homes built for vacation income alongside resort-style amenities.
Median sold: $560K · Median days on market: 19 · Sold-to-list: 99.1% · Source: Stellar MLS
About 0.6 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
Aggregate statistics from recent Stellar MLS closed sales and live MLS inventory. A market read, not an appraisal of any home or a listing of individual sales.
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Ryan's Take on Windsor Cay
Windsor Cay Resort draws a specific kind of buyer: the investor who wants their vacation home to work for them even when they're not there. This is a purpose-built short-term rental community in south Clermont, zoned for nightly rentals and structured from the ground up for vacation income — which is rare in Central Florida, where most communities actively prohibit it.
The demand anchor here is straightforward: Walt Disney World is roughly ten to fifteen minutes away. That proximity is the engine behind the rental economics, and it's why buyers from across the country — and internationally — target this corridor. You don't need to live in Orlando to own here; you need a property manager and a booking calendar.
The housing stock reflects that purpose. Pulte built these homes with high-occupancy use in mind — up to ten bedrooms, private heated pools, open great rooms, and resort finishes throughout. The community amenities replicate what guests expect from a hotel: lazy river, water slides, mini golf, arcade, on-site dining, fitness center, and a 24-hour staffed entrance. The HOA bundles cable, internet, and landscaping so that owners experience genuine hands-off ownership.
Buyers comparison-shopping Windsor Cay typically look at two other communities: Solterra Resort in Davenport and Windsor at Westside, both within the same Four Corners vacation rental corridor. Windsor Cay's newer construction and expanded resort amenity package are the main differentiators for buyers choosing between them.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Windsor Cay · 2nd Quarter 2026
394 sales · Stellar MLS · last 12 mo
$560K
Median Sale Price
19 days
Median Days on Market
99.1%
Sold-to-List
$223
Median $/sqft
Recent Sales Map
Recent sales activity in Windsor Cay
Currently For Sale
21 active listings in Windsor Cay

$268/sqft
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$298/sqft
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$286/sqft
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$285/sqft
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$298/sqft
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$302/sqft
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$289/sqft
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$270/sqft
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$229/sqft
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$344/sqft
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$297/sqft
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$278/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool |
|---|---|---|---|---|---|---|
| 8 | 6 | 4,026 | $1,080,000 | $268 | 67 | ✓ |
| 5 | 6 | 2,605 | $775,000 | $298 | 142 | ✓ |
| 5 | 5 | 2,269 | $649,900 | $286 | 1 | ✓ |
| 5 | 5 | 2,281 | $649,900 | $285 | 1 | ✓ |
| 5 | 5 | 2,281 | $680,000 | $298 | 129 | ✓ |
| 5 | 5 | 2,269 | $685,000 | $302 | 36 | ✓ |
| 5 | 5 | 2,281 | $660,000 | $289 | 57 | ✓ |
| 7 | 6 | 3,274 | $885,000 | $270 | 129 | ✓ |
| 8 | 6 | 4,034 | $925,000 | $229 | 271 | ✓ |
| 7 | 6 | 3,274 | $1,125,000 | $344 | 1 | ✓ |
| 10 | 8 | 4,376 | $1,299,000 | $297 | 235 | ✓ |
| 5 | 5 | 2,281 | $635,000 | $278 | 135 | ✓ |
| 6 | 5 | 3,127 | $799,000 | $256 | 14 | ✓ |
| 7 | 6 | 3,286 | $919,000 | $280 | 8 | ✓ |
| 7 | 6 | 3,286 | $958,900 | $292 | 8 | ✓ |
| 10 | 8 | 4,376 | $1,595,000 | $364 | 48 | ✓ |
| 8 | 6 | 4,026 | $1,196,000 | $297 | 115 | ✓ |
| 8 | 6 | 4,026 | $1,196,000 | $297 | 54 | ✓ |
| 10 | 8 | 4,382 | $1,495,000 | $341 | 1 | ✓ |
| 5 | 5 | 2,281 | $675,000 | $296 | 18 | ✓ |
| 5 | 5 | 2,281 | $599,999 | $263 | 0 | ✓ |
Windsor Cay Market — Common Questions
Is Windsor Cay a buyer's or seller's market in 2026?+
Windsor Cay is currently a seller's market with about 0.6 months of inventory. About 0.6 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
What is the median home sale price in Windsor Cay?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Windsor Cay is approximately $560K, up about 2.9% from a year earlier.
How many homes are for sale in Windsor Cay?+
There are currently 21 active listings in Windsor Cay, with homes selling at roughly 32.8 per month. That works out to about 0.6 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated June 29, 2026 at 4:37 AM ET· Powered by Stellar MLS
MLS Data:Active and pending listing data is sourced from the Stellar MLS as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The MLS GRID does not guarantee the accuracy of this data, which may not reflect all real estate activity in the area.
Sold Data: Sales analysis is derived from Florida Department of Revenue public property records(arm's-length transactions). Ryan Solberg and MaxLife Realty LLC are not affiliated with Windsor Cayor its HOA. This report is not intended to solicit properties already listed for sale nor to cause a breach of an existing agency relationship. Data should be independently verified. E&OE.
Based on information submitted to the MLS GRID as of June 26, 2026 at 2:54 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 26, 2026 at 2:54 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA