MLS data updated Jun 7, 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.
Avg. sold: $524K · Avg. days on market: 75 · Sold-to-list: 96.8% · Source: Stellar MLS
Currently For Sale
50 active listings in Windsor Hills
$180/sqft
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$459/sqft
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$235/sqft
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$254/sqft
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$220/sqft
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$400/sqft
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$296/sqft
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$450/sqft
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$156/sqft
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$222/sqft
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$176/sqft
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$432/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|
| 7 | 5 | 3,599 | $649,000 | $180 | 495 | ✓ | — | Water |
| 6 | 5 | 4,679 | $2,150,000 | $459 | 184 | ✓ | ✓ | Water |
| 8 | 7 | 3,612 | $849,900 | $235 | 94 | ✓ | — | — |
| 4 | 2 | 1,834 | $465,000 | $254 | 27 | — | — | — |
| 3 | 3 | 1,755 | $386,000 | $220 | 104 | — | — | — |
| 6 | 4 | 2,915 | $1,165,000 | $400 | 177 | — | — | — |
| 2 | 2 | 1,211 | $359,000 | $296 | 221 | — | — | — |
| 5 | 5 | 4,440 | $1,999,999 | $450 | 2 | ✓ | — | — |
| 5 | 4 | 2,845 | $444,999 | $156 | 61 | — | — | — |
| 2 | 2 | 1,465 | $325,000 | $222 | 3 | — | — | — |
| 5 | 4 | 2,845 | $499,900 | $176 | 45 | — | — | — |
| 5 | 3 | 2,197 | $949,900 | $432 | 177 | — | — | — |
| 3 | 2 | 2,130 | $595,000 | $279 | 218 | — | — | — |
| 5 | 5 | 2,630 | $599,999 | $228 | 415 | — | — | — |
| 5 | 4 | 2,630 | $575,000 | $219 | 249 | — | — | — |
| 5 | 5 | 4,205 | $2,195,000 | $522 | 2 | — | — | — |
| 1 | 1 | 882 | $309,000 | $350 | 54 | — | — | Water |
| 5 | 7 | 5,563 | $2,225,000 | $400 | 288 | ✓ | — | — |
| 4 | 2 | 1,567 | $395,000 | $252 | 1 | ✓ | — | — |
| 5 | 4 | 2,677 | $475,000 | $177 | 225 | ✓ | — | — |
| 5 | 7 | 5,668 | $1,697,900 | $300 | 130 | ✓ | — | — |
| 2 | 2 | 1,081 | $269,000 | $249 | 170 | — | — | — |
| 3 | 3 | 1,736 | $434,000 | $250 | 0 | — | — | — |
| 4 | 3 | 1,636 | $390,000 | $238 | 139 | ✓ | — | — |
| 2 | 3 | 1,161 | $289,000 | $249 | 4 | — | — | — |
| 3 | 4 | 2,233 | $475,000 | $213 | 83 | ✓ | — | — |
| 5 | 5 | 2,265 | $428,000 | $189 | 1 | ✓ | — | — |
| 1 | 1 | 855 | $285,000 | $333 | 1 | — | — | — |
| 6 | 6 | 3,419 | $949,900 | $278 | 1 | ✓ | — | — |
| 4 | 3 | 2,295 | $639,900 | $279 | 1 | — | — | — |
| 5 | 5 | 3,117 | $930,000 | $298 | 1 | ✓ | — | — |
| 3 | 2 | 1,354 | $324,900 | $240 | 1 | — | — | — |
| 4 | 4 | 1,645 | $330,000 | $201 | 1 | — | — | — |
| 6 | 5 | 2,987 | $590,990 | $198 | 1 | ✓ | — | — |
| 6 | 4 | 3,778 | $1,390,000 | $368 | 47 | — | — | — |
| 7 | 6 | 3,314 | $600,000 | $181 | 118 | ✓ | — | Water |
| 11 | 13 | 5,496 | $1,195,000 | $217 | 118 | ✓ | — | — |
| 3 | 3 | 1,755 | $325,000 | $185 | 51 | — | — | — |
| — | 0 | — | $799,000 | — | 63 | — | — | — |
| 3 | 3 | 1,638 | $579,900 | $354 | 2 | — | — | — |
| 5 | 4 | 2,317 | $475,000 | $205 | 33 | ✓ | — | — |
| 4 | 3 | 2,469 | $864,990 | $350 | 68 | — | — | — |
| 3 | 3 | 1,845 | $609,000 | $330 | 254 | — | — | — |
| 5 | 5 | 2,294 | $470,000 | $205 | 282 | ✓ | — | — |
| 3 | 2 | 2,066 | $555,000 | $269 | 5 | — | — | — |
| 5 | 5 | 3,600 | $1,550,000 | $431 | 17 | ✓ | — | Water |
| 6 | 4 | 2,604 | $595,000 | $228 | 244 | ✓ | ✓ | Sunset Lakes |
| 4 | 2 | 1,701 | $429,000 | $252 | 7 | ✓ | ✓ | Water |
| 6 | 4 | 2,870 | $535,000 | $186 | 23 | ✓ | — | — |
| 3 | 2 | 1,640 | $495,000 | $302 | 37 | — | — | — |
Under Contract
20 homes pending in Windsor Hills · Avg. $626K
Recent Sales Analysis
62 homes sold in Windsor Hills over the past 12 months · Stellar MLS
Approximate sale locations — dots are offset ±1 home for privacy
| Beds | Baths | Sq Ft | Listed | Sold | List Price | Sold Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 3 | 3 | 1,440 | 11/28/25 | 5/30/26 | $454,900 | $454,000 | $315 | 183 | ✓ | — | — |
| 4 | 4 | 1,824 | 5/27/26 | 5/29/26 | $585,000 | $585,000 | $321 | 2 | ✓ | — | — |
| 3 | 3 | 1,440 | 5/2/26 | 5/28/26 | $415,000 | $405,000 | $281 | 26 | ✓ | — | — |
| 5 | 5 | 2,297 | 5/31/25 | 5/27/26 | $719,990 | $680,000 | $296 | 361 | ✓ | — | — |
| 5 | 5 | 2,297 | 5/5/26 | 5/8/26 | $644,900 | $640,000 | $279 | 3 | ✓ | — | — |
| 7 | 4 | 2,876 | 5/4/26 | 5/5/26 | $700,000 | $700,000 | $243 | 1 | ✓ | — | — |
| 3 | 3 | 1,440 | 12/26/25 | 4/30/26 | $439,000 | $420,000 | $292 | 125 | ✓ | — | — |
| 3 | 3 | 1,440 | 4/23/26 | 4/30/26 | $415,000 | $416,000 | $289 | 7 | ✓ | — | — |
| 3 | 3 | 1,440 | 4/10/26 | 4/17/26 | $425,000 | $415,000 | $288 | 7 | ✓ | — | — |
| 6 | 4 | 2,469 | 1/13/26 | 4/10/26 | $649,500 | $620,000 | $251 | 87 | ✓ | — | — |
| 3 | 3 | 1,440 | 7/28/25 | 4/9/26 | $385,000 | $350,000 | $243 | 255 | ✓ | — | — |
| 5 | 5 | 2,342 | 1/30/26 | 3/20/26 | $665,000 | $655,000 | $280 | 49 | ✓ | — | — |
| 6 | 4 | 2,812 | 3/10/26 | 3/17/26 | $609,900 | $595,000 | $212 | 7 | ✓ | — | — |
| 6 | 4 | 2,812 | 1/21/26 | 3/16/26 | $749,000 | $702,000 | $250 | 54 | ✓ | — | Water |
| 3 | 3 | 1,440 | 2/7/26 | 3/13/26 | $400,000 | $375,000 | $260 | 34 | ✓ | — | — |
| 3 | 3 | 1,440 | 2/21/26 | 3/12/26 | $414,900 | $395,000 | $274 | 19 | ✓ | — | — |
| 3 | 2 | 1,410 | 3/10/26 | 3/10/26 | $350,000 | $350,000 | $248 | 0 | — | — | — |
| 6 | 4 | 2,812 | 2/17/26 | 2/24/26 | $685,000 | $675,000 | $240 | 7 | ✓ | — | — |
| 3 | 3 | 1,440 | 12/20/25 | 2/13/26 | $429,000 | $420,000 | $292 | 55 | ✓ | — | — |
| 5 | 5 | 2,297 | 2/12/26 | 2/12/26 | $600,000 | $600,000 | $261 | 0 | ✓ | — | — |
| 4 | 4 | 1,824 | 1/13/26 | 2/10/26 | $610,000 | $595,000 | $326 | 28 | ✓ | — | — |
| 3 | 3 | 1,440 | 11/5/25 | 2/6/26 | $375,999 | $330,000 | $229 | 93 | ✓ | — | — |
| 3 | 3 | 1,440 | 5/15/25 | 1/12/26 | $384,900 | $360,000 | $250 | 242 | ✓ | — | Water |
| 6 | 4 | 2,812 | 12/23/25 | 12/30/25 | $669,000 | $650,000 | $231 | 7 | ✓ | — | — |
| 5 | 5 | 2,342 | 12/15/25 | 12/23/25 | $650,000 | $627,750 | $268 | 8 | ✓ | — | — |
| 6 | 4 | 2,812 | 11/29/25 | 12/17/25 | $725,000 | $725,000 | $258 | 18 | ✓ | — | — |
| 3 | 3 | 1,440 | 11/21/25 | 12/15/25 | $412,900 | $405,900 | $282 | 24 | ✓ | — | — |
| 5 | 5 | 2,297 | 4/10/25 | 12/5/25 | $619,000 | $615,000 | $268 | 239 | ✓ | — | — |
| 3 | 3 | 1,440 | 10/30/25 | 12/3/25 | $385,000 | $375,000 | $260 | 34 | ✓ | — | — |
| 6 | 4 | 2,812 | 6/8/25 | 11/26/25 | $689,000 | $657,500 | $234 | 171 | ✓ | — | — |
| 3 | 3 | 1,440 | 6/20/25 | 11/24/25 | $400,000 | $380,000 | $264 | 157 | ✓ | — | Water |
| 4 | 4 | 1,824 | 11/8/25 | 11/17/25 | $624,900 | $624,900 | $343 | 9 | ✓ | — | — |
| 5 | 5 | 2,342 | 7/13/25 | 11/14/25 | $604,900 | $595,000 | $254 | 124 | ✓ | — | — |
| 5 | 5 | 2,342 | 11/4/25 | 11/14/25 | $619,999 | $600,000 | $256 | 10 | ✓ | — | — |
| 6 | 4 | 2,812 | 4/15/25 | 11/12/25 | $626,000 | $618,000 | $220 | 211 | ✓ | — | — |
| 6 | 4 | 2,812 | 4/7/25 | 11/10/25 | $650,000 | $630,000 | $224 | 217 | ✓ | — | — |
| 6 | 4 | 2,812 | 10/26/25 | 11/10/25 | $735,000 | $718,000 | $255 | 15 | ✓ | — | — |
| 3 | 3 | 1,440 | 10/31/25 | 11/10/25 | $395,000 | $386,000 | $268 | 10 | ✓ | — | — |
| 7 | 4 | 2,812 | 8/15/25 | 11/3/25 | $729,000 | $729,000 | $259 | 80 | ✓ | — | — |
| 3 | 3 | 1,440 | 8/11/25 | 10/24/25 | $395,000 | $375,000 | $260 | 74 | ✓ | — | — |
| 3 | 3 | 1,440 | 10/1/25 | 10/20/25 | $395,000 | $385,000 | $267 | 19 | ✓ | — | — |
| 3 | 3 | 1,440 | 10/7/25 | 10/16/25 | $395,000 | $391,000 | $272 | 9 | ✓ | — | — |
| 3 | 3 | 1,440 | 5/19/25 | 10/14/25 | $467,000 | $390,000 | $271 | 148 | ✓ | — | — |
| 3 | 3 | 1,440 | 9/29/25 | 10/9/25 | $415,000 | $410,000 | $285 | 10 | ✓ | — | — |
| 3 | 3 | 1,440 | 4/20/25 | 9/29/25 | $415,000 | $407,000 | $283 | 162 | ✓ | — | — |
| 4 | 4 | 1,878 | 3/17/25 | 9/15/25 | $520,000 | $400,000 | $213 | 182 | ✓ | — | — |
| 5 | 5 | 2,342 | 9/3/25 | 9/5/25 | $649,000 | $642,000 | $274 | 2 | ✓ | — | — |
| 5 | 5 | 2,342 | 6/19/25 | 9/4/25 | $680,000 | $680,000 | $290 | 77 | ✓ | — | — |
| 6 | 4 | 2,812 | 6/23/25 | 8/29/25 | $739,900 | $648,800 | $231 | 67 | ✓ | ✓ | Lake Reedy |
| 3 | 3 | 1,440 | 4/4/25 | 8/26/25 | $385,000 | $400,000 | $278 | 144 | ✓ | — | — |
| 5 | 5 | 2,342 | 7/24/25 | 8/14/25 | $639,000 | $600,000 | $256 | 21 | ✓ | — | — |
| 3 | 3 | 1,440 | 8/5/25 | 8/14/25 | $420,000 | $405,000 | $281 | 9 | ✓ | — | — |
| 3 | 3 | 1,440 | 8/6/25 | 8/8/25 | $415,000 | $400,000 | $278 | 2 | ✓ | — | — |
| 5 | 5 | 2,342 | 4/10/25 | 8/1/25 | $624,900 | $613,500 | $262 | 113 | ✓ | — | — |
| 4 | 4 | 1,824 | 7/3/25 | 7/31/25 | $580,000 | $575,000 | $315 | 28 | ✓ | — | — |
| 3 | 3 | 1,440 | 5/7/25 | 7/15/25 | $414,999 | $405,000 | $281 | 69 | ✓ | — | — |
| 3 | 3 | 1,440 | 4/24/25 | 7/11/25 | $379,000 | $385,000 | $267 | 78 | ✓ | — | — |
| 5 | 5 | 2,848 | 5/25/25 | 7/7/25 | $585,000 | $565,000 | $198 | 43 | ✓ | — | — |
| 5 | 5 | 2,342 | 2/23/25 | 7/7/25 | $629,999 | $600,000 | $256 | 134 | ✓ | — | — |
| 6 | 4 | 2,812 | 6/24/25 | 6/30/25 | $668,000 | $665,000 | $236 | 6 | ✓ | — | — |
Free · No Obligation
What Is Your Windsor Hills Home Worth?
I analyze active competition, recent sales, and neighborhood trends to give you a precise estimate of what your home is worth right now — no automated Zestimate, a real analysis from a local expert.
Ryan Solberg
MaxLife Realty
321.373.3536
Report generated June 7, 2026 at 5:59 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 Stellar MLS closed-sale 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 7, 2026 at 5:05 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 7, 2026 at 5:05 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.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA