Windsor Hills
The Closest Resort Community to Disney
Kissimmee, FL
A mature, gated resort community prized for being among the closest short-term-rental neighborhoods to Walt Disney World — consistently high occupancy thanks to its location and resort amenities.
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Ryan's Take on Windsor Hills
Windsor Hills draws a buyer who has done the math on short-term rental demand and likes what they see. Sitting roughly five minutes from Walt Disney World's front gate — closer than almost any other gated resort community in the region — it occupies a location vacation-home investors find very difficult to replicate elsewhere in Greater Orlando. Whether a family is buying for personal use and placing it in a rental program when away, or an investor is acquiring a pure income asset, the Disney proximity anchor is the reason they're here.
The employment story is equally direct: Walt Disney World is one of the largest single employers in the state, and the US-192 hospitality corridor extends that reach across thousands of additional positions in hotels, restaurants, and retail. Full-time residents often include cast members and hospitality workers who appreciate living close to work inside a resort-grade community.
The housing stock leans toward vacation-configured floor plans — open living, multiple en-suite bedrooms, tile throughout — built between 2004 and 2010. The clubhouse campus adds pools, a water park, movie theater, and sports courts. Buyers seeking comparable amenities at a different scale typically cross-shop Reunion Resort or Solterra Resort, both nearby STR-permitted communities serving the same investor profile.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Recent Sales Map
59 recent individual sales in and around Windsor Hills · FL public records · no addresses published
Approximate sale locations — dots are offset ±1 home for privacy
| Beds | Baths | Sq Ft | Listed | Sold ▼ | List Price | Sold Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|---|---|---|
| — | — | 7,512 | — | 9/1/25 | — | $2,604,400 | $347 | — |
| — | — | 4,340 | — | 9/1/25 | — | $1,695,000 | $391 | — |
| — | — | 2,796 | — | 9/1/25 | — | $820,000 | $293 | — |
| — | — | 2,410 | — | 9/1/25 | — | $772,000 | $320 | — |
| — | — | 1,863 | — | 9/1/25 | — | $770,000 | $413 | — |
| — | — | 2,074 | — | 9/1/25 | — | $722,500 | $348 | — |
| — | — | 3,754 | — | 9/1/25 | — | $708,500 | $189 | — |
| — | — | 3,866 | — | 9/1/25 | — | $655,000 | $169 | — |
| — | — | 1,708 | — | 9/1/25 | — | $650,000 | $381 | — |
| — | — | 3,663 | — | 9/1/25 | — | $650,000 | $177 | — |
| — | — | 3,485 | — | 9/1/25 | — | $625,000 | $179 | — |
| — | — | 1,803 | — | 9/1/25 | — | $620,000 | $344 | — |
| — | — | 1,863 | — | 9/1/25 | — | $570,000 | $306 | — |
| — | — | 3,075 | — | 9/1/25 | — | $535,000 | $174 | — |
| — | — | 3,637 | — | 9/1/25 | — | $530,000 | $146 | — |
| — | — | 3,465 | — | 9/1/25 | — | $519,000 | $150 | — |
| — | — | 2,863 | — | 9/1/25 | — | $510,000 | $178 | — |
| — | — | 2,480 | — | 9/1/25 | — | $430,000 | $173 | — |
| — | — | 2,440 | — | 9/1/25 | — | $415,000 | $170 | — |
| — | — | 2,224 | — | 9/1/25 | — | $400,000 | $180 | — |
| — | — | 1,875 | — | 9/1/25 | — | $400,000 | $213 | — |
| — | — | 1,974 | — | 9/1/25 | — | $379,000 | $192 | — |
| — | — | 2,015 | — | 9/1/25 | — | $369,000 | $183 | — |
| — | — | 1,773 | — | 9/1/25 | — | $345,000 | $195 | — |
| — | — | 6,419 | — | 8/1/25 | — | $2,710,000 | $422 | — |
| — | — | 3,259 | — | 8/1/25 | — | $1,335,000 | $410 | — |
| — | — | 3,743 | — | 8/1/25 | — | $1,330,000 | $355 | — |
| — | — | 4,085 | — | 8/1/25 | — | $1,153,000 | $282 | — |
| — | — | 3,720 | — | 8/1/25 | — | $700,400 | $188 | — |
| — | — | 3,720 | — | 8/1/25 | — | $695,000 | $187 | — |
| — | — | 2,661 | — | 8/1/25 | — | $680,000 | $256 | — |
| — | — | 3,935 | — | 8/1/25 | — | $675,000 | $172 | — |
| — | — | 3,663 | — | 8/1/25 | — | $660,000 | $180 | — |
| — | — | 3,115 | — | 8/1/25 | — | $648,800 | $208 | — |
| — | — | 4,691 | — | 8/1/25 | — | $640,000 | $136 | — |
| — | — | 3,653 | — | 8/1/25 | — | $638,000 | $175 | — |
| — | — | 2,661 | — | 8/1/25 | — | $600,000 | $225 | — |
| — | — | 3,118 | — | 8/1/25 | — | $590,000 | $189 | — |
| — | — | 1,410 | — | 8/1/25 | — | $562,200 | $399 | — |
| — | — | 3,228 | — | 8/1/25 | — | $554,000 | $172 | — |
| — | — | 2,811 | — | 8/1/25 | — | $520,000 | $185 | — |
| — | — | 2,713 | — | 8/1/25 | — | $500,000 | $184 | — |
| — | — | 2,069 | — | 8/1/25 | — | $496,000 | $240 | — |
| — | — | 3,465 | — | 8/1/25 | — | $480,000 | $139 | — |
| — | — | 1,977 | — | 8/1/25 | — | $425,000 | $215 | — |
| — | — | 1,875 | — | 8/1/25 | — | $390,000 | $208 | — |
| — | — | 2,124 | — | 8/1/25 | — | $315,000 | $148 | — |
| — | — | 1,338 | — | 8/1/25 | — | $285,000 | $213 | — |
| — | — | 4,893 | — | 7/1/25 | — | $1,400,000 | $286 | — |
| — | — | 3,586 | — | 7/1/25 | — | $820,000 | $229 | — |
| — | — | 4,107 | — | 7/1/25 | — | $739,000 | $180 | — |
| — | — | 3,757 | — | 7/1/25 | — | $708,400 | $189 | — |
| — | — | 3,757 | — | 7/1/25 | — | $669,400 | $178 | — |
| — | — | 3,596 | — | 7/1/25 | — | $575,000 | $160 | — |
| — | — | 2,540 | — | 7/1/25 | — | $490,000 | $193 | — |
| — | — | 1,272 | — | 7/1/25 | — | $360,000 | $283 | — |
| — | — | 1,608 | — | 7/1/25 | — | $330,000 | $205 | — |
| — | — | 2,124 | — | 7/1/25 | — | $300,000 | $141 | — |
| — | — | 1,587 | — | 7/1/25 | — | $250,000 | $158 | — |
Currently For Sale
0 active listings in Windsor Hills
Windsor Hills Market — Common Questions
Is Windsor Hills a buyer's or seller's market in 2026?+
Recent public-record sales volume in Windsor Hills is currently too low to call the market definitively. Contact Ryan Solberg at MaxLife Realty for a current read.
How many homes are for sale in Windsor Hills?+
There are currently 0 active listings in Windsor Hills.
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated June 27, 2026 at 11:37 PM 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 Hillsor 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 27, 2026 at 11:37 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 28, 2026. 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