Windsor Hill
Avg. sold: $985K · Avg. DOM: 36 · Sold-to-list: 96.2% · Source: Stellar MLS
Ryan's Take on Windsor Hill
Windsor Hill is a gated luxury community in the Windermere address — which means Butler Chain of Lakes proximity, the Windermere school zone, and the cultural weight of one of the most recognized luxury residential corridors in Florida — at a price point and community scale that sits meaningfully below the Isleworth and Keene's Pointe ceiling. The community offers guard-gated security, established HOA governance, and architectural standards that maintain consistency across its custom and semi-custom home stock. Lot sizes run generous by suburban standards, and the mature canopy in the established sections gives the streetscape the settled character that newer Windermere communities are still building toward.
The buyer here is typically a professional family that has decided Windermere is the right address — schools, proximity to the Butler Chain, the theme-park commute on SR-429, the established prestige of the corridor — and is selecting Windsor Hill because it delivers the core Windermere experience without the membership complexity and carrying costs of a private club community. Windermere Preparatory School, consistently ranked the top private K-12 in Orange County, is minutes away as an alternative to the public school feeder. Cross-shop is Keene's Pointe for the buyer who wants the Jack Nicklaus Golden Bear Club golf experience embedded in their daily life, or the non-gated Windermere streets off Main Street for the buyer who wants the Windermere address without HOA governance. Windsor Hill sits in the middle of that range as a well-governed, established gated community with the Windermere character without the private-club commitment.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Under Contract
20 homes pending in Windsor Hill · Avg. $1.7M
Windsor Hill · 2nd Quarter 2026
13 sales · Stellar MLS
$950K
Median Sale Price
36 days
Avg. Days on Market
96.2%
Sold-to-List
$283
Avg. $/sqft
Recent Sales Analysis
13 homes sold in Windsor Hill over the past 3 years · 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 | View |
|---|---|---|---|---|---|---|---|---|---|---|
| 4 | 3 | 2,967 | 4/19/26 | 4/20/26 | $950,000 | $950,000 | $320 | 1 | ✓ | — |
| 5 | 4 | 3,924 | 9/28/25 | 9/30/25 | $1,100,000 | $1,070,000 | $273 | 2 | ✓ | — |
| 5 | 3 | 2,878 | 4/18/25 | 5/16/25 | $929,900 | $920,000 | $320 | 28 | ✓ | Water |
| 4 | 4 | 3,997 | 4/18/25 | 4/28/25 | $1,050,000 | $900,000 | $225 | 10 | ✓ | — |
| 5 | 6 | 5,297 | 10/7/24 | 4/2/25 | $1,450,000 | $1,250,000 | $236 | 177 | ✓ | — |
| 6 | 5 | 3,817 | 9/27/24 | 10/1/24 | $775,000 | $798,000 | $209 | 4 | ✓ | — |
| 5 | 4 | 4,116 | 5/19/24 | 6/27/24 | $1,350,000 | $1,300,000 | $316 | 39 | ✓ | — |
| 4 | 3 | 3,000 | 4/10/24 | 4/12/24 | $995,000 | $995,000 | $332 | 2 | ✓ | — |
| 6 | 6 | 3,941 | 4/9/24 | 4/11/24 | $900,000 | $900,000 | $228 | 2 | ✓ | — |
| 5 | 4 | 3,636 | 1/8/24 | 1/16/24 | $1,090,000 | $1,050,000 | $289 | 8 | ✓ | — |
| 4 | 3 | 2,463 | 6/28/23 | 12/27/23 | $949,000 | $860,000 | $349 | 182 | ✓ | — |
| 4 | 3 | 3,018 | 9/23/23 | 9/28/23 | $869,900 | $850,000 | $282 | 5 | ✓ | — |
| 4 | 3 | 3,181 | 7/26/23 | 7/28/23 | $975,000 | $962,500 | $303 | 2 | ✓ | — |
Currently For Sale
50 active listings in Windsor Hill
$429/sqft
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$429/sqft
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$331/sqft
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$234/sqft
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$347/sqft
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$280/sqft
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$371/sqft
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$233/sqft
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$439/sqft
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$212/sqft
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$417/sqft
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$228/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|
| 5 | 4 | 4,867 | $2,090,000 | $429 | 15 | ✓ | ✓ | Lake Clarice |
| 4 | 4 | 2,791 | $1,198,000 | $429 | 59 | ✓ | — | — |
| 5 | 3 | 2,539 | $840,000 | $331 | 5 | ✓ | — | — |
| 4 | 3 | 2,411 | $565,000 | $234 | 65 | — | — | — |
| 4 | 5 | 2,450 | $849,900 | $347 | 1 | ✓ | — | — |
| 3 | 2 | 1,877 | $525,000 | $280 | 1 | — | — | — |
| 3 | 2 | 1,819 | $675,000 | $371 | 1 | ✓ | — | — |
| 5 | 3 | 3,050 | $710,000 | $233 | 197 | ✓ | ✓ | Water |
| 3 | 2 | 1,935 | $850,000 | $439 | 7 | — | ✓ | Lake Butler - Butler Chain |
| 5 | 5 | 3,697 | $783,000 | $212 | 70 | — | — | — |
| 4 | 3 | 2,816 | $1,175,000 | $417 | 7 | ✓ | — | — |
| 6 | 6 | 3,336 | $760,000 | $228 | 533 | — | — | — |
| 4 | 3 | 3,516 | $975,000 | $277 | 7 | — | — | — |
| 4 | 4 | 2,720 | $625,000 | $230 | 35 | — | — | — |
| 6 | 10 | 11,100 | $13,900,000 | $1,252 | 1 | ✓ | ✓ | Lake Butler |
| 6 | 7 | 7,349 | $4,995,000 | $680 | 106 | ✓ | ✓ | Lake Down/Butler Chain Of Lake |
| 4 | 3 | 2,575 | $635,000 | $247 | 1 | — | — | — |
| 4 | 3 | 3,001 | $628,000 | $209 | 1 | — | — | — |
| 4 | 6 | 4,268 | $4,200,000 | $984 | 1 | ✓ | — | — |
| 5 | 4 | 3,929 | $1,450,000 | $369 | 1 | ✓ | — | — |
| 4 | 4 | 2,742 | $765,000 | $279 | 39 | — | — | Water |
| 6 | 7 | 7,016 | $2,999,990 | $428 | 3 | ✓ | ✓ | Lake Olivia |
| 4 | 4 | 2,690 | $749,900 | $279 | 7 | ✓ | — | — |
| 7 | 10 | 8,362 | $7,795,000 | $932 | 418 | ✓ | ✓ | Lake Tibet Butler |
| 4 | 3 | 2,053 | $649,994 | $317 | 89 | — | — | — |
| 6 | 5 | 3,463 | $1,397,000 | $403 | 34 | — | — | — |
| — | 0 | — | $1,000,000 | — | 0 | — | — | Water |
| 4 | 3 | 2,599 | $1,149,000 | $442 | 76 | ✓ | — | — |
| 6 | 6 | 6,000 | $3,195,000 | $533 | 134 | ✓ | ✓ | Lake Davis |
| 3 | 2 | 2,058 | $510,000 | $248 | 2 | — | — | — |
| 4 | 4 | 5,273 | $3,450,000 | $654 | 135 | ✓ | ✓ | Lake Down |
| 6 | 5 | 4,625 | $1,098,000 | $237 | 115 | — | — | — |
| 3 | 2 | 2,469 | $749,995 | $304 | 68 | — | — | — |
| 4 | 4 | 3,387 | $1,150,000 | $340 | 7 | ✓ | — | — |
| 4 | 5 | 4,013 | $1,999,999 | $498 | 52 | ✓ | — | — |
| 5 | 7 | 5,036 | $2,550,000 | $506 | 1 | ✓ | — | — |
| 5 | 9 | 7,058 | $3,290,000 | $466 | 1 | ✓ | — | — |
| — | 0 | — | $900,000 | — | 347 | — | — | — |
| 5 | 4 | 3,971 | $1,150,000 | $290 | 2 | ✓ | — | Water |
| 6 | 9 | 8,038 | $7,999,000 | $995 | 11 | ✓ | — | — |
| 4 | 4 | 4,052 | $1,450,000 | $358 | 41 | ✓ | — | — |
| 5 | 5 | 3,835 | $1,350,000 | $352 | 84 | ✓ | — | — |
| 5 | 5 | 3,868 | $1,499,999 | $388 | 21 | ✓ | — | — |
| 5 | 7 | 7,099 | $7,250,000 | $1,021 | 147 | ✓ | — | — |
| 4 | 5 | 3,399 | $1,439,000 | $423 | 53 | ✓ | — | — |
| 4 | 3 | 2,221 | $539,000 | $243 | 18 | — | — | — |
| 3 | 3 | 1,649 | $561,738 | $341 | 42 | — | — | — |
| 5 | 6 | 5,323 | $2,599,000 | $488 | 32 | ✓ | — | — |
| 4 | 2 | 2,987 | $832,000 | $279 | 1 | — | — | — |
| 5 | 8 | 7,529 | $7,400,000 | $983 | 35 | ✓ | ✓ | Lake Tibet/Butler |
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated June 13, 2026 at 11:15 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 Stellar MLS closed-sale 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 June 13, 2026 at 9:23 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 June 13, 2026 at 9:23 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.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA