Windsor Hill
Median sold: $1.0M · Median DOM: 34 · Sold-to-list: 96.3% · Source: Stellar MLS
About 5.7 months of inventory — supply and demand are roughly even, so neither side has a clear edge (4–6 months = balanced).
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 Hill
Windsor Hill draws a specific kind of buyer — established professionals and executive families who want genuine Windermere estate living without the resort-brand energy of larger master-planned communities. These are households that want space and privacy and are done compromising on either.
The SR-429 and SR-408 corridors put Windsor Hill residents within practical reach of Walt Disney World's corporate campuses, the Universal Orlando corridor, and the major healthcare systems along I-4. For a dual-income household where one partner works Sand Lake Road and the other is on the I-Drive corridor, this address solves the map in a way few Windermere communities can match at this scale of home.
What makes the housing stock distinctive is its age and character. These are custom and semi-custom homes from the late 1980s through the 2010s — generous floor plans starting in the mid-3,000s and running well past 5,000 square feet on larger builds, mature landscaping, and the quiet streetscape that newer communities are still decades away from achieving. The Butler Chain of Lakes is minutes away, and the school pipeline through Bridgewater Middle into Olympia or Windermere High is genuinely strong.
Buyers who shop Windsor Hill cross-compare it with Keene's Pointe and the Estates at Windermere — without a golf membership requirement and with a character that feels more like old Windermere than a planned amenity campus.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Under Contract
20 homes pending in Windsor Hill · Avg. $1.9M
Windsor Hill · 3rd Quarter 2026
449 sales · Stellar MLS · last 12 mo
$1.0M
Median Sale Price
34 days
Median Days on Market
96.3%
Sold-to-List
$307
Median $/sqft
Recent Sales Map
60 recent individual sales in and around Windsor Hill · 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 |
|---|---|---|---|---|---|---|---|---|
| — | — | 5,721 | — | 12/1/25 | — | $4,400,000 | $769 | — |
| — | — | 7,222 | — | 12/1/25 | — | $3,150,000 | $436 | — |
| — | — | 5,916 | — | 12/1/25 | — | $2,460,000 | $416 | — |
| — | — | 6,829 | — | 12/1/25 | — | $2,250,000 | $329 | — |
| — | — | 4,044 | — | 12/1/25 | — | $1,875,000 | $464 | — |
| — | — | 4,848 | — | 12/1/25 | — | $1,465,000 | $302 | — |
| — | — | 3,264 | — | 12/1/25 | — | $1,450,000 | $444 | — |
| — | — | 5,120 | — | 12/1/25 | — | $1,420,000 | $277 | — |
| — | — | 3,813 | — | 12/1/25 | — | $1,375,000 | $361 | — |
| — | — | 4,226 | — | 12/1/25 | — | $1,300,000 | $308 | — |
| — | — | 3,014 | — | 12/1/25 | — | $1,230,000 | $408 | — |
| — | — | 4,175 | — | 12/1/25 | — | $1,160,000 | $278 | — |
| — | — | 4,089 | — | 12/1/25 | — | $935,000 | $229 | — |
| — | — | 3,938 | — | 12/1/25 | — | $925,000 | $235 | — |
| — | — | 3,662 | — | 12/1/25 | — | $900,000 | $246 | — |
| — | — | 3,072 | — | 12/1/25 | — | $665,000 | $216 | — |
| — | — | 2,072 | — | 12/1/25 | — | $619,000 | $299 | — |
| — | — | 2,981 | — | 12/1/25 | — | $600,000 | $201 | — |
| — | — | 1,925 | — | 12/1/25 | — | $570,000 | $296 | — |
| — | — | 1,947 | — | 12/1/25 | — | $520,000 | $267 | — |
| — | — | 1,819 | — | 12/1/25 | — | $510,000 | $280 | — |
| — | — | 2,154 | — | 12/1/25 | — | $507,500 | $236 | — |
| — | — | 1,745 | — | 12/1/25 | — | $500,000 | $287 | — |
| — | — | 13,559 | — | 11/1/25 | — | $11,100,000 | $819 | — |
| — | — | 8,431 | — | 11/1/25 | — | $5,500,000 | $652 | — |
| — | — | 6,367 | — | 11/1/25 | — | $3,800,000 | $597 | — |
| — | — | 4,324 | — | 11/1/25 | — | $3,550,000 | $821 | — |
| — | — | 6,489 | — | 11/1/25 | — | $3,178,500 | $490 | — |
| — | — | 1,366 | — | 11/1/25 | — | $2,750,000 | $2,013 | — |
| — | — | 5,693 | — | 11/1/25 | — | $2,400,000 | $422 | — |
| — | — | 5,590 | — | 11/1/25 | — | $1,980,000 | $354 | — |
| — | — | 4,199 | — | 11/1/25 | — | $1,675,000 | $399 | — |
| — | — | 4,475 | — | 11/1/25 | — | $1,435,000 | $321 | — |
| — | — | 3,586 | — | 11/1/25 | — | $1,370,000 | $382 | — |
| — | — | 3,617 | — | 11/1/25 | — | $1,275,000 | $353 | — |
| — | — | 4,202 | — | 11/1/25 | — | $1,150,000 | $274 | — |
| — | — | 3,267 | — | 11/1/25 | — | $1,150,000 | $352 | — |
| — | — | 3,053 | — | 11/1/25 | — | $1,120,000 | $367 | — |
| — | — | 2,390 | — | 11/1/25 | — | $930,000 | $389 | — |
| — | — | 2,262 | — | 11/1/25 | — | $775,000 | $343 | — |
| — | — | 3,800 | — | 11/1/25 | — | $750,000 | $197 | — |
| — | — | 3,399 | — | 11/1/25 | — | $722,500 | $213 | — |
| — | — | 2,854 | — | 11/1/25 | — | $710,000 | $249 | — |
| — | — | 3,103 | — | 11/1/25 | — | $705,000 | $227 | — |
| — | — | 3,313 | — | 11/1/25 | — | $700,000 | $211 | — |
| — | — | 2,542 | — | 11/1/25 | — | $700,000 | $275 | — |
| — | — | 2,827 | — | 11/1/25 | — | $670,000 | $237 | — |
| — | — | 2,042 | — | 11/1/25 | — | $670,000 | $328 | — |
| — | — | 2,644 | — | 11/1/25 | — | $660,000 | $250 | — |
| — | — | 2,631 | — | 11/1/25 | — | $615,000 | $234 | — |
| — | — | 1,819 | — | 11/1/25 | — | $555,000 | $305 | — |
| — | — | 2,165 | — | 11/1/25 | — | $544,000 | $251 | — |
| — | — | 1,723 | — | 11/1/25 | — | $515,000 | $299 | — |
| — | — | 10,362 | — | 10/1/25 | — | $9,000,000 | $869 | — |
| — | — | 8,555 | — | 10/1/25 | — | $4,800,000 | $561 | — |
| — | — | 6,265 | — | 10/1/25 | — | $3,840,000 | $613 | — |
| — | — | 6,219 | — | 10/1/25 | — | $2,750,000 | $442 | — |
| — | — | 4,061 | — | 10/1/25 | — | $2,350,000 | $579 | — |
| — | — | 4,929 | — | 10/1/25 | — | $2,250,000 | $456 | — |
| — | — | 4,345 | — | 10/1/25 | — | $2,100,000 | $483 | — |
Currently For Sale
50 active listings in Windsor Hill
$300/sqft
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$263/sqft
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$499/sqft
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$399/sqft
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$507/sqft
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$466/sqft
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$206/sqft
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$243/sqft
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$395/sqft
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$276/sqft
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$406/sqft
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$301/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|
| 3 | 2 | 2,066 | $619,000 | $300 | 2 | — | — | — |
| 3 | 3 | 2,720 | $715,000 | $263 | 1 | — | — | Water |
| 5 | 6 | 5,935 | $2,960,000 | $499 | 23 | ✓ | ✓ | Water |
| 3 | 2 | 2,258 | $899,999 | $399 | 24 | ✓ | — | — |
| 6 | 7 | 6,308 | $3,200,000 | $507 | 304 | ✓ | — | — |
| 4 | 6 | 4,810 | $2,240,000 | $466 | 308 | ✓ | — | — |
| 5 | 5 | 3,697 | $760,000 | $206 | 111 | — | — | — |
| 5 | 4 | 3,820 | $930,000 | $243 | 181 | — | — | — |
| 4 | 3 | 2,224 | $879,000 | $395 | 132 | ✓ | — | — |
| 6 | 5 | 4,999 | $1,380,000 | $276 | 294 | — | — | Water |
| 6 | 7 | 7,016 | $2,850,000 | $406 | 45 | ✓ | ✓ | Lake Olivia |
| 3 | 3 | 1,725 | $520,000 | $301 | 97 | — | — | — |
| 4 | 5 | 2,450 | $824,900 | $337 | 41 | ✓ | — | — |
| 5 | 3 | 2,618 | $699,000 | $267 | 37 | — | — | — |
| 5 | 4 | 3,929 | $1,400,000 | $356 | 62 | ✓ | — | — |
| 5 | 5 | 4,228 | $2,099,995 | $497 | 135 | ✓ | ✓ | Butler Chain Of Lakes |
| 5 | 5 | 4,380 | $1,070,000 | $244 | 89 | ✓ | — | — |
| 3 | 5 | 5,004 | $4,300,000 | $859 | 105 | ✓ | — | Water |
| 4 | 4 | 2,618 | $975,000 | $372 | 364 | — | — | — |
| 5 | 4 | 3,182 | $890,000 | $280 | 64 | — | — | — |
| 6 | 5 | 3,463 | $1,375,000 | $397 | 76 | — | — | — |
| 5 | 3 | 2,511 | $639,000 | $254 | 194 | — | — | — |
| 5 | 3 | 3,300 | $1,575,000 | $477 | 455 | ✓ | — | — |
| 7 | 14 | 51,000 | $30,000,000 | $588 | 51 | ✓ | ✓ | Lake Down On Butler Chain |
| 5 | 6 | 7,740 | $4,599,000 | $594 | 160 | ✓ | ✓ | Lake Butler |
| 3 | 5 | 4,262 | $3,699,000 | $868 | 323 | ✓ | — | Water |
| 5 | 3 | 5,316 | $9,750,000 | $1,834 | 272 | ✓ | ✓ | Butler Chain Of Lakes |
| — | 0 | — | $9,750,000 | — | 219 | — | ✓ | Lake Down-Butler Chain |
| 4 | 5 | 4,136 | $2,550,000 | $617 | 30 | ✓ | — | — |
| 3 | 2 | 1,706 | $599,000 | $351 | 5 | — | — | — |
| 5 | 7 | 5,471 | $6,500,000 | $1,188 | 28 | ✓ | — | — |
| 6 | 7 | 4,665 | $5,300,000 | $1,136 | 59 | ✓ | — | Water |
| 4 | 3 | 2,947 | $679,999 | $231 | 198 | — | — | — |
| 4 | 5 | 4,037 | $2,150,000 | $533 | 79 | ✓ | ✓ | The Gardens Pond |
| 4 | 4 | 3,166 | $1,595,000 | $504 | 6 | ✓ | — | — |
| 3 | 5 | 6,236 | $4,190,000 | $672 | 94 | ✓ | — | Water |
| 6 | 4 | 4,176 | $1,080,000 | $259 | 155 | ✓ | — | — |
| 6 | 5 | 4,625 | $1,095,000 | $237 | 162 | — | — | — |
| 5 | 4 | 3,486 | $1,569,000 | $450 | 31 | ✓ | — | — |
| 4 | 4 | 2,690 | $749,900 | $279 | 49 | ✓ | — | — |
| 6 | 8 | 6,781 | $2,800,000 | $413 | 3 | ✓ | ✓ | — |
| 5 | 3 | 2,831 | $1,275,000 | $450 | 4 | — | ✓ | Butler Chain Of Lakes |
| 4 | 3 | 2,357 | $940,000 | $399 | 79 | ✓ | — | — |
| 4 | 3 | 2,988 | $915,000 | $306 | 134 | ✓ | — | — |
| 4 | 3 | 2,665 | $749,900 | $281 | 42 | — | ✓ | Lake Speer |
| 5 | 5 | 3,868 | $1,450,000 | $375 | 80 | ✓ | — | — |
| 4 | 3 | 3,001 | $624,900 | $208 | 45 | — | — | — |
| 4 | 4 | 3,736 | $2,375,000 | $636 | 50 | — | ✓ | Lake Davis |
| 5 | 4 | 3,267 | $1,050,000 | $321 | 4 | ✓ | — | — |
| 5 | 4 | 4,202 | $925,000 | $220 | 71 | — | — | — |
Windsor Hill Market — Common Questions
Is Windsor Hill a buyer's or seller's market in 2026?+
Windsor Hill is currently a balanced market with about 5.7 months of inventory. About 5.7 months of inventory — supply and demand are roughly even, so neither side has a clear edge (4–6 months = balanced).
What is the median home sale price in Windsor Hill?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Windsor Hill is approximately $1.0M, down about 9.6% from a year earlier.
How many homes are for sale in Windsor Hill?+
There are currently 213 active listings in Windsor Hill, with homes selling at roughly 37.4 per month. That works out to about 5.7 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated July 23, 2026 at 7:39 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 Hillor 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 July 23, 2026 at 6:51 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.
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 July 23, 2026 at 6:51 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