MLS data updated Oct 30, 2026
Windsor at WestsideReal Estate Market Report · October 2026
Windsor at Westside real estate market report · Kissimmee, FL
Kissimmee, FL
Windsor at Westside is a residential community in Kissimmee, Florida. This live report tracks active and pending listings, 12-month sale prices and days on market, and public-record sales for the surrounding ZIP.
Median sold: $495K · Median days on market: 94 · Sold-to-list: 96.2% · Source: Stellar MLS, last 12 mo
About 2.6 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 Stellar MLS closed sales over the last 12 months and live MLS inventory. A market read, not an appraisal of any home or a listing of individual sales.
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Windsor at Westside by the numbers
34 listings are active in Windsor at Westside right now, priced from $380K to $678K, with a median of $472K. Single-family homes make up 53% of the 34 listings shown, followed by townhomes at 47%. Where living area is reported, the 4- to 9-bedroom properties run 2,102 to 4,391 square feet of living area. Year built spans 2015 to 2020.
34 listings have a private pool; the median active listing has been on the market 73 days; recent sales have closed near $168 per square foot.
160 sales closed here in the last 12 months at a median of $495K, about 13.3 a month against 2.6 months of current inventory.
Figures are aggregates of the active listings shown on this page and of 12-month MLS sales, as of October 30, 2026.
Under Contract
3 homes pending in Windsor at Westside · Avg. $424K
Windsor at Westside · 4th Quarter 2026
160 sales · Stellar MLS · last 12 mo
$495K
Median Sale Price
94 days
Median Days on Market
96.2%
Sold-to-List
$168
Median $/sqft
Currently For Sale
34 active listings in Windsor at Westside
$172/sqft
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$185/sqft
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$183/sqft
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$174/sqft
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$168/sqft
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$199/sqft
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$208/sqft
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$175/sqft
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$152/sqft
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$184/sqft
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$162/sqft
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$219/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool |
|---|---|---|---|---|---|---|
| 5 | 5 | 2,265 | $389,900 | $172 | 3 | ✓ |
| 5 | 4 | 2,263 | $419,000 | $185 | 801 | ✓ |
| 5 | 5 | 2,263 | $415,000 | $183 | 2 | ✓ |
| 7 | 6 | 3,314 | $575,000 | $174 | 179 | ✓ |
| 5 | 5 | 2,263 | $380,000 | $168 | 4 | ✓ |
| 5 | 5 | 2,263 | $449,990 | $199 | 4 | ✓ |
| 5 | 5 | 2,263 | $469,990 | $208 | 87 | ✓ |
| 5 | 5 | 2,263 | $394,900 | $175 | 541 | ✓ |
| 6 | 5 | 3,142 | $479,000 | $152 | 151 | ✓ |
| 5 | 5 | 2,263 | $416,000 | $184 | 29 | ✓ |
| 8 | 6 | 4,041 | $655,000 | $162 | 79 | ✓ |
| 5 | 4 | 2,492 | $544,990 | $219 | 95 | ✓ |
| 5 | 5 | 2,263 | $437,500 | $193 | 7 | ✓ |
| 9 | 6 | 4,391 | $678,000 | $154 | 10 | ✓ |
| 5 | 5 | 2,263 | $390,000 | $172 | 65 | ✓ |
| 5 | 5 | 2,265 | $440,000 | $194 | 139 | ✓ |
| 4 | 4 | 2,102 | $415,000 | $197 | 27 | ✓ |
| 8 | 6 | 4,034 | $629,900 | $156 | 63 | ✓ |
| 5 | 5 | 2,263 | $409,990 | $181 | 17 | ✓ |
| 5 | 4 | 2,492 | $455,000 | $183 | 526 | ✓ |
| 5 | 4 | 2,492 | $459,000 | $184 | 105 | ✓ |
| 9 | 6 | 4,391 | $669,990 | $153 | 107 | ✓ |
| 4 | 4 | 2,102 | $404,000 | $192 | 195 | ✓ |
| 5 | 4 | 2,492 | $479,000 | $192 | 182 | ✓ |
| 5 | 4 | 2,492 | $475,000 | $191 | 51 | ✓ |
| 5 | 5 | 2,263 | $499,000 | $221 | 893 | ✓ |
| 8 | 6 | 4,041 | $570,000 | $141 | 150 | ✓ |
| 7 | 6 | 3,281 | $550,000 | $168 | 336 | ✓ |
| 5 | 5 | 2,263 | $419,000 | $185 | 24 | ✓ |
| 8 | 6 | 4,041 | $570,000 | $141 | 25 | ✓ |
| 9 | 6 | 4,391 | $658,000 | $150 | 181 | ✓ |
| 8 | 6 | 4,041 | $644,900 | $160 | 66 | ✓ |
| 8 | 6 | 4,041 | $649,900 | $161 | 66 | ✓ |
| 8 | 6 | 4,041 | $570,000 | $141 | 25 | ✓ |
Windsor at Westside Market — Common Questions
Is Windsor at Westside a buyer's or seller's market in 2026?+
Windsor at Westside is currently a seller's market with about 2.6 months of inventory. About 2.6 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 at Westside?+
Based on Stellar MLS closed sales over the last 12 months, the median sale price in Windsor at Westside is approximately $495K.
How many homes are for sale in Windsor at Westside?+
There are currently 34 active listings in Windsor at Westside, with homes selling at roughly 13.3 per month. That works out to about 2.6 months of inventory.
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Report generated October 30, 2026 at 10:30 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 at Westsideor 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 30, 2026 at 9:53 AM 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 at Westside
Utilities & Services
Windsor at Westside 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 30, 2026 at 9:53 AM 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