Windsor HillReal Estate Market Report · October 2026
Median sold: $965K · Median DOM: 33 · Sold-to-list: 96.2% · Source: Stellar MLS, last 12 mo
About 4.5 months of inventory — supply and demand are roughly even, so neither side has a clear edge (4–6 months = balanced).
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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Ryan's Take on Windsor Hill
Windsor Hill fits buyers who want genuine Windermere estate living without the resort-brand energy of larger master-planned communities — space and privacy, without 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. If you're juggling two commutes, one to Sand Lake Road and one to 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 schools named for the area include Bridgewater Middle and Olympia or Windermere High; assignment follows the street address, so check each home in OCPS Find My School.
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
14 homes pending in Windsor Hill · Avg. $967K
Windsor Hill · 4th Quarter 2026
530 sales · Stellar MLS · last 12 mo
$965K
Median Sale Price
33 days
Median Days on Market
96.2%
Sold-to-List
$318
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
$441/sqft
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$718/sqft
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$609/sqft
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$263/sqft
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$670/sqft
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$331/sqft
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$242/sqft
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$291/sqft
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$342/sqft
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$380/sqft
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$429/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|
| 5 | 7 | 6,105 | $2,695,000 | $441 | 1 | ✓ | ✓ | Lake Burden |
| 5 | 8 | 9,403 | $6,750,000 | $718 | 1 | ✓ | ✓ | Lake Butler, Butler Chain Of Lakes |
| 5 | 6 | 4,430 | $2,700,000 | $609 | 1 | ✓ | — | — |
| 4 | 3 | 3,038 | $799,900 | $263 | 8 | — | — | Water |
| — | 0 | — | $900,000 | — | 1 | — | — | — |
| 4 | 5 | 5,152 | $3,450,000 | $670 | 2 | ✓ | ✓ | Lake Down |
| 5 | 4 | 3,929 | $1,299,900 | $331 | 162 | ✓ | — | — |
| 4 | 4 | 2,311 | $559,900 | $242 | 6 | — | — | — |
| 4 | 3 | 2,214 | $645,000 | $291 | 45 | — | — | — |
| 9 | 16 | 20,445 | $6,999,999 | $342 | 10 | ✓ | — | — |
| 4 | 3 | 2,892 | $1,100,000 | $380 | 3 | — | — | — |
| 5 | 5 | 3,612 | $1,550,000 | $429 | 4 | — | ✓ | Lake Cawood |
| 3 | 2 | 1,706 | $579,000 | $339 | 98 | — | — | — |
| 5 | 4 | 3,656 | $1,500,000 | $410 | 79 | ✓ | — | — |
| 6 | 7 | 4,945 | $1,799,000 | $364 | 11 | ✓ | ✓ | Water |
| 4 | 4 | 2,454 | $630,000 | $257 | 7 | — | — | — |
| 4 | 3 | 3,018 | $1,160,000 | $384 | 10 | — | — | — |
| 6 | 6 | 5,031 | $1,999,000 | $397 | 318 | — | — | — |
| 4 | 3 | 2,984 | $1,050,000 | $352 | 21 | — | — | — |
| 4 | 4 | 3,912 | $1,999,000 | $511 | 28 | ✓ | — | — |
| 5 | 6 | 5,580 | $3,999,000 | $717 | 33 | ✓ | — | — |
| 4 | 6 | 4,812 | $2,240,000 | $466 | 78 | ✓ | — | — |
| 4 | 5 | 4,512 | $2,899,000 | $643 | 288 | ✓ | — | — |
| 4 | 4 | 3,687 | $1,799,000 | $488 | 254 | ✓ | — | Water |
| 4 | 5 | 4,290 | $3,150,000 | $734 | 25 | ✓ | — | — |
| 5 | 7 | 7,223 | $3,600,000 | $498 | 5 | ✓ | — | — |
| 3 | 3 | 1,984 | $580,000 | $292 | 3 | — | — | — |
| 4 | 4 | 3,153 | $939,990 | $298 | 208 | — | — | — |
| 4 | 3 | 2,740 | $919,990 | $336 | 189 | — | — | — |
| 6 | 5 | 3,794 | $1,296,000 | $342 | 288 | ✓ | — | — |
| 5 | 3 | 3,356 | $1,299,000 | $387 | 62 | ✓ | — | — |
| 5 | 4 | 4,186 | $1,300,000 | $311 | 64 | ✓ | — | — |
| 4 | 3 | 2,680 | $950,000 | $354 | 44 | ✓ | ✓ | — |
| 3 | 3 | 1,853 | $527,500 | $285 | 81 | — | — | — |
| 5 | 5 | 4,219 | $1,648,000 | $391 | 72 | ✓ | — | — |
| 5 | 4 | 2,976 | $680,000 | $228 | 383 | — | — | — |
| 4 | 3 | 2,460 | $625,000 | $254 | 60 | — | — | — |
| 5 | 7 | 6,970 | $6,650,000 | $954 | 92 | ✓ | — | — |
| 4 | 3 | 2,427 | $625,000 | $258 | 5 | ✓ | — | — |
| 4 | 3 | 2,224 | $775,000 | $348 | 69 | ✓ | — | — |
| 4 | 4 | 3,315 | $800,000 | $241 | 393 | — | — | — |
| 3 | 5 | 4,333 | $3,595,000 | $830 | 33 | ✓ | — | Water |
| 5 | 5 | 3,612 | $1,475,000 | $408 | 10 | — | ✓ | Lake Cawood |
| 5 | 5 | 5,972 | $3,600,000 | $603 | 94 | ✓ | — | Water |
| 5 | 5 | 5,511 | $5,600,000 | $1,016 | 100 | ✓ | ✓ | Lake Butler |
| 5 | 7 | 5,747 | $2,685,000 | $467 | 52 | ✓ | — | — |
| 6 | 4 | 4,858 | $2,500,000 | $515 | 113 | ✓ | ✓ | Lake Olivia |
| 4 | 4 | 3,646 | $1,065,000 | $292 | 108 | — | — | — |
| 4 | 6 | 7,669 | $3,500,000 | $456 | 88 | ✓ | — | — |
| 4 | 2 | 2,020 | $530,000 | $262 | 52 | ✓ | — | — |
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 4.5 months of inventory. About 4.5 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 Stellar MLS closed sales over the last 12 months, the median sale price in Windsor Hill is approximately $965K.
How many homes are for sale in Windsor Hill?+
There are currently 199 active listings in Windsor Hill, with homes selling at roughly 44.2 per month. That works out to about 4.5 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 organized. Moves very quickly. Broad reaching resources, up-to-date advertising methods. Hard working, has all the materials for staging on hand — and sold in less than 30 days.”
“Wow, what an amazing experience. Ryan was able to help me find the best home in Windermere. He is very knowledgeable and very resourceful. He helped me close a very big deal.”
Guides about Windsor Hill
Report generated October 31, 2026 at 10:49 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 October 31, 2026 at 6:48 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 Hill
Utilities & Services
Windsor Hill is in Orange County, Florida. Here's who to call to get power, water, and trash service set up in your name before closing.
Electric
Orlando Utilities Commission (OUC) · (407) 423-9018City of Orlando and parts of unincorporated Orange County. OUC also provides water in its territory.
Duke Energy Florida · (800) 700-8744Most of unincorporated Orange County, plus Winter Garden, Apopka, and Ocoee.
Water & Sewer
Orange County Utilities · (407) 836-5515Unincorporated Orange County (water & sewer).
OUC — Water (City of Orlando) · (407) 423-9018City of Orlando — OUC provides both water and electric.
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 31, 2026 at 6:48 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