MLS data updated Oct 6, 2026
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.
Median sold: $492K · Median days on market: 59 · Sold-to-list: 96.5% · Source: Stellar MLS
About 9.1 months of inventory — supply is outpacing demand, so buyers have room to negotiate (over 6 months = buyer'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 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 you're buying for personal use and placing it in a rental program when away, or 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. If you work at Disney or in hospitality, you can live 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
Under Contract
20 homes pending in Windsor Hills · Avg. $891K
Windsor Hills · 4th Quarter 2026
1385 sales · Stellar MLS · last 12 mo
$492K
Median Sale Price
59 days
Median Days on Market
96.5%
Sold-to-List
$233
Median $/sqft
Recent Sales Map
Recent sales activity in Windsor Hills
Currently For Sale
50 active listings in Windsor Hills
$244/sqft
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$210/sqft
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$184/sqft
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$169/sqft
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$226/sqft
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$198/sqft
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$198/sqft
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$165/sqft
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$199/sqft
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$255/sqft
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$253/sqft
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$264/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|
| 5 | 6 | 2,587 | $630,000 | $244 | 51 | ✓ | — | — |
| 6 | 5 | 3,142 | $660,000 | $210 | 52 | ✓ | — | — |
| 5 | 5 | 2,263 | $416,000 | $184 | 6 | ✓ | — | — |
| 4 | 3 | 1,862 | $314,000 | $169 | 148 | — | — | — |
| 6 | 5 | 2,987 | $675,000 | $226 | 1 | ✓ | — | — |
| 5 | 5 | 2,294 | $455,000 | $198 | 7 | ✓ | — | — |
| 3 | 4 | 1,962 | $389,000 | $198 | 77 | ✓ | — | — |
| 3 | 3 | 2,124 | $349,900 | $165 | 92 | — | — | — |
| 4 | 2 | 1,656 | $329,000 | $199 | 146 | ✓ | — | — |
| 3 | 2 | 1,570 | $400,000 | $255 | 24 | — | — | — |
| 3 | 3 | 1,187 | $300,000 | $253 | 6 | ✓ | — | — |
| 3 | 3 | 1,440 | $380,000 | $264 | 355 | ✓ | — | — |
| 9 | 7 | 4,363 | $685,000 | $157 | 26 | ✓ | — | — |
| 2 | 2 | 1,432 | $369,900 | $258 | 34 | — | — | — |
| 2 | 2 | 1,430 | $475,000 | $332 | 48 | — | — | — |
| 3 | 2 | 1,307 | $317,500 | $243 | 27 | — | — | — |
| 3 | 3 | 1,837 | $670,000 | $365 | 167 | — | — | Water |
| 3 | 3 | 1,295 | $310,000 | $239 | 78 | ✓ | — | — |
| 3 | 3 | 1,794 | $626,990 | $349 | 41 | — | — | — |
| 3 | 3 | 1,794 | $607,990 | $339 | 41 | — | — | — |
| 3 | 3 | 1,651 | $560,990 | $340 | 168 | — | — | — |
| 3 | 3 | 1,628 | $548,990 | $337 | 366 | — | — | — |
| 3 | 3 | 1,628 | $549,990 | $338 | 366 | — | — | — |
| 3 | 3 | 1,794 | $610,990 | $341 | 366 | — | — | — |
| 3 | 2 | 1,228 | $379,900 | $309 | 1 | ✓ | — | — |
| — | 0 | — | $375,000 | — | 334 | — | — | — |
| 6 | 5 | 2,294 | $500,000 | $218 | 69 | ✓ | — | — |
| 3 | 3 | 1,708 | $390,000 | $228 | 251 | — | — | — |
| 5 | 5 | 2,263 | $388,000 | $171 | 26 | ✓ | — | — |
| 3 | 3 | 2,158 | $814,990 | $378 | 98 | — | — | — |
| 3 | 4 | 2,544 | $759,000 | $298 | 8 | — | — | — |
| 5 | 5 | 3,076 | $535,000 | $174 | 152 | ✓ | — | — |
| 4 | 3 | 1,791 | $469,990 | $262 | 55 | ✓ | — | — |
| 5 | 6 | 4,266 | $1,499,000 | $351 | 2 | ✓ | — | — |
| 3 | 3 | 1,372 | $335,000 | $244 | 19 | — | — | — |
| 8 | 6 | 4,041 | $644,900 | $160 | 43 | ✓ | — | — |
| 2 | 2 | 1,211 | $399,900 | $330 | 26 | — | — | — |
| 8 | 6 | 4,041 | $560,000 | $139 | 70 | ✓ | — | — |
| 7 | 7 | 4,093 | $749,000 | $183 | 54 | ✓ | — | — |
| 4 | 5 | 1,948 | $569,000 | $292 | 82 | — | — | — |
| 3 | 3 | 1,659 | $399,000 | $241 | 102 | — | — | — |
| 4 | 4 | 1,824 | $549,999 | $302 | 35 | ✓ | — | — |
| 4 | 3 | 2,388 | $889,000 | $372 | 13 | — | — | — |
| 4 | 3 | 1,902 | $334,899 | $176 | 16 | ✓ | — | — |
| 7 | 5 | 2,914 | $629,900 | $216 | 32 | ✓ | ✓ | Water |
| 8 | 5 | 2,914 | $559,900 | $192 | 272 | ✓ | — | — |
| 4 | 3 | 1,902 | $334,900 | $176 | 32 | ✓ | — | — |
| 4 | 3 | 1,636 | $420,000 | $257 | 121 | ✓ | — | Water |
| 4 | 5 | 1,804 | $409,000 | $227 | 931 | — | — | — |
| 3 | 3 | 1,440 | $395,000 | $274 | 97 | ✓ | — | — |
Windsor Hills Market — Common Questions
Is Windsor Hills a buyer's or seller's market in 2026?+
Windsor Hills is currently a buyer's market with about 9.1 months of inventory. About 9.1 months of inventory — supply is outpacing demand, so buyers have room to negotiate (over 6 months = buyer's market).
What is the median home sale price in Windsor Hills?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Windsor Hills is approximately $492K.
How many homes are for sale in Windsor Hills?+
There are currently 1054 active listings in Windsor Hills, with homes selling at roughly 115.4 per month. That works out to about 9.1 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
5.0 ★ · 42 reviews
What clients say
All 42 reviews on Zillow“Highly likely to recommend! Ryan helped us sell my mother's condo when she needed to move to assisted living. But that was just the start — he helped us find repairmen for the things that needed fixing.”
“Mortgage broker and real estate broker — great services. I've bought and sold many houses and Ryan Solberg is the best realtor I've ever had. Great attitude, highly energetic, extremely knowledgeable.”
Report generated October 7, 2026 at 12:57 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 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 October 6, 2026 at 9:45 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.
Moving to Windsor Hills
Utilities & Services
Windsor Hills is in Osceola County, Florida. Here's who to call to get power, water, and trash service set up in your name before closing.
Electric
Kissimmee Utility Authority (KUA) · (407) 933-9800City of Kissimmee.
Orlando Utilities Commission (OUC) · (407) 423-9018City of St. Cloud (OUC has run St. Cloud's electric system since 1997).
Water & Sewer
Toho Water Authority · (407) 944-5000Kissimmee, St. Cloud, Poinciana, and many unincorporated areas.
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 October 6, 2026 at 9:45 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