BUTLER CHAIN OF LAKES · PRIVATE GATED
Windermere
Windermere is old-money Florida at its quietest — a tree-shaded isthmus town of 3,000 where the lake is always visible from the road, the neighbors have been here for decades, and the privacy of Isleworth or Keene's Pointe is just minutes away. Life here is organized around the water: morning boat rides on a 13-lake chain, sunset cocktails on private docks, and the deliberate calm of a place that has never needed to advertise itself.
Median sold: $1.0M · Median DOM: 34 · Sold-to-list: 96.3% · Source: Stellar MLS
About 5 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 Windermere
Windermere is the oldest continuously inhabited town in Orange County west of Orlando, founded in 1889 on an isthmus between Lake Down and Lake Butler — and the Butler Chain of Lakes is the entire point. Thirteen interconnected lakes, 32 navigable canals, more than 5,000 acres of water with Outstanding Florida Waters designation since 1985. Isleworth is on the Butler Chain. Keene's Pointe surrounds it on 1,200 acres with a Jack Nicklaus Golden Bear course. The Reserve at Lake Butler Sound offers 48 custom estate homesites on 1–10 acres with the most private shoreline positions in the metro. Pricing reflects all of that: Windermere runs roughly 43% higher than comparable Dr. Phillips tiers for the same square footage and age. You're not paying for the house; you're paying for the water, the prestige, and the irreplaceable 30–40 year oak canopy in Keene's Pointe that no new development can replicate.
The community itself is a genuine Florida small town, and that's the thing buyers from Atlanta or New York don't expect. Main Street has the Friday farmers market, Dixie Cream Cafe, Paloma Coffee, Pizza 14 — a walkable village center that predates every master-planned community in the metro by a century. Schools are strong: Windermere Elementary, Bridgewater Middle (9/10 GreatSchools, STEM-focused), and Windermere High (Niche A−, #65 in Florida, #4 in Orange County). Windermere Preparatory School, the only IB school in Central Florida and Niche's #1 private school in Orange County, sits minutes away. If the buyer's priority is the Butler Chain and they're serious about waterfront living, this is where the conversation starts. If they're trying to buy Windermere on a Dr. Phillips budget, I'll tell them honestly: Keene's Pointe interior homes represent the best value entry, and the tree canopy alone justifies the premium.
— Ryan Solberg, Broker/Owner, MaxLife Realty
Under Contract
20 homes pending in Windermere · Avg. $2.0M
Windermere · 3rd Quarter 2026
500 sales · Stellar MLS · last 12 mo
$1.0M
Median Sale Price
34 days
Median Days on Market
96.3%
Sold-to-List
$311
Median $/sqft
Recent Sales Map
60 recent individual sales in and around Windermere · 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 | — |
| — | — | 2,042 | — | 11/1/25 | — | $670,000 | $328 | — |
| — | — | 2,827 | — | 11/1/25 | — | $670,000 | $237 | — |
| — | — | 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 Windermere
$306/sqft
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$206/sqft
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$241/sqft
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$301/sqft
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$278/sqft
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$465/sqft
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$477/sqft
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$631/sqft
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$486/sqft
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$276/sqft
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$497/sqft
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$995/sqft
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| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM | Pool | Waterfront | View |
|---|---|---|---|---|---|---|---|---|
| 4 | 4 | 3,646 | $1,114,900 | $306 | 2 | — | — | — |
| 5 | 5 | 3,697 | $760,000 | $206 | 105 | — | — | — |
| 4 | 4 | 2,675 | $645,000 | $241 | 50 | — | — | — |
| 3 | 3 | 1,725 | $520,000 | $301 | 91 | — | — | — |
| 3 | 3 | 2,014 | $558,900 | $278 | 2 | — | — | Water |
| 2 | 2 | 1,398 | $649,999 | $465 | 58 | — | — | — |
| 5 | 3 | 3,300 | $1,575,000 | $477 | 449 | ✓ | — | — |
| 4 | 5 | 4,676 | $2,950,000 | $631 | 237 | ✓ | — | — |
| 4 | 6 | 4,810 | $2,340,000 | $486 | 302 | ✓ | — | — |
| 6 | 5 | 4,999 | $1,380,000 | $276 | 288 | — | — | Water |
| 5 | 5 | 4,228 | $2,099,995 | $497 | 129 | ✓ | ✓ | Butler Chain Of Lakes |
| 6 | 9 | 8,038 | $7,999,000 | $995 | 53 | ✓ | — | — |
| 5 | 4 | 3,820 | $930,000 | $243 | 175 | — | — | — |
| 4 | 3 | 2,224 | $895,000 | $402 | 126 | ✓ | — | — |
| 4 | 4 | 3,736 | $2,375,000 | $636 | 44 | — | ✓ | Lake Davis |
| 7 | 9 | 14,068 | $15,900,000 | $1,130 | 2 | ✓ | ✓ | Lake Tibet |
| 5 | 4 | 3,751 | $1,595,000 | $425 | 2 | ✓ | — | — |
| 4 | 3 | 2,698 | $749,900 | $278 | 119 | ✓ | ✓ | Cawood |
| 5 | 4 | 4,876 | $2,250,000 | $461 | 92 | ✓ | — | — |
| 6 | 9 | 8,305 | $5,000,000 | $602 | 333 | ✓ | ✓ | Keenes Pointe Pond |
| 4 | 5 | 4,512 | $2,999,999 | $665 | 182 | ✓ | — | — |
| 3 | 5 | 5,004 | $4,300,000 | $859 | 99 | ✓ | — | Water |
| 4 | 4 | 3,086 | $1,649,000 | $534 | 22 | ✓ | ✓ | Lake Crescent |
| 5 | 4 | 3,929 | $1,400,000 | $356 | 56 | ✓ | — | — |
| 5 | 3 | 2,620 | $699,999 | $267 | 93 | ✓ | — | — |
| 4 | 2 | 2,521 | $655,000 | $260 | 77 | — | — | — |
| 6 | 7 | 7,016 | $2,850,000 | $406 | 39 | ✓ | ✓ | Lake Olivia |
| 5 | 4 | 3,064 | $1,259,000 | $411 | 56 | ✓ | — | — |
| 5 | 5 | 4,380 | $1,070,000 | $244 | 83 | ✓ | — | — |
| 4 | 4 | 5,273 | $3,350,000 | $635 | 171 | ✓ | ✓ | Lake Down |
| 4 | 3 | 3,297 | $1,750,000 | $531 | 45 | ✓ | ✓ | Lake Crescent |
| 4 | 4 | 2,791 | $1,195,000 | $428 | 98 | ✓ | — | — |
| 4 | 3 | 2,214 | $650,000 | $294 | 45 | — | — | — |
| 4 | 3 | 3,100 | $1,049,990 | $339 | 102 | — | — | — |
| 4 | 3 | 2,221 | $519,000 | $234 | 56 | — | — | — |
| 4 | 3 | 3,478 | $1,190,000 | $342 | 14 | ✓ | — | — |
| 3 | 3 | 1,699 | $599,990 | $353 | 4 | — | — | — |
| 5 | 5 | 2,959 | $669,900 | $226 | 4 | — | — | — |
| 4 | 6 | 5,515 | $2,099,900 | $381 | 17 | ✓ | ✓ | Lake Whitney |
| 5 | 4 | 3,567 | $2,100,000 | $589 | 45 | ✓ | — | — |
| 4 | 4 | 4,052 | $1,450,000 | $358 | 78 | ✓ | — | — |
| 4 | 3 | 2,053 | $639,994 | $312 | 141 | — | — | — |
| 4 | 3 | 2,887 | $1,295,000 | $449 | 24 | — | — | — |
| 6 | 5 | 4,625 | $1,095,000 | $237 | 156 | — | — | — |
| 3 | 2 | 2,258 | $899,999 | $399 | 18 | ✓ | — | — |
| 5 | 3 | 2,272 | $564,900 | $249 | 51 | — | — | — |
| 6 | 4 | 4,482 | $2,450,000 | $547 | 88 | ✓ | ✓ | Lake Olivia |
| 4 | 3 | 2,740 | $1,039,091 | $379 | 83 | — | — | — |
| 4 | 5 | 2,450 | $849,900 | $347 | 35 | ✓ | — | — |
| 3 | 3 | 2,177 | $679,000 | $312 | 14 | — | — | — |
Windermere Market — Common Questions
Is Windermere a buyer's or seller's market in 2026?+
Windermere is currently a balanced market with about 5 months of inventory. About 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 Windermere?+
Based on Florida Department of Revenue public records over the last 6 months, the median sale price in Windermere is approximately $1.0M.
How many homes are for sale in Windermere?+
There are currently 210 active listings in Windermere, with homes selling at roughly 41.7 per month. That works out to about 5 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
Report generated July 16, 2026 at 8:06 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 Florida Department of Revenue public property records(arm's-length transactions). Ryan Solberg and MaxLife Realty LLC are not affiliated with Windermereor 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 16, 2026 at 8:01 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 July 16, 2026 at 8:01 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.
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