Homes for Sale in Windermere, FL
261 homes are for sale in Windermere, FL as of 2026-09-06, with 22 more under contract. The median list price is $930,000 ($322/sq ft), most homes list between $410K to $3.95M, and the median listing has been on the market 41 days. 61 homes came on the market this week and 440 sold in the last 12 months at a median of $640,000.
Newest homes for sale in Windermere
The most recently listed homes in Windermere, newest first, with photos. Each card opens the full listing with every photo, the community’s sales history and a tour request. Homes marked New listed in the last seven days.
Windermere homes for sale by price
Every active listing in Windermere grouped by price, with the newest listings in each band. The median is $930,000; the busiest band is $1M and up.
$200K – $300K: 2 homes
- $299,500 · 2 bd / 2 ba / 1,161 sq ft · 8180 BOAT HOOK LOOP #109 (Lakeside/Lks)
- $295,000 · 2 bd / 2 ba / 1,161 sq ft · 8180 BOAT HOOK LOOP #102 (Lakeside/Lks/Windermere)
$300K – $400K: 21 homes
- $360,000 · 2 bd / 2.5 ba / 1,311 sq ft · 12417 CRUXBURY DRIVE (Lakes/Windermere-Lk Reams Twhm)
- $320,000 · 3 bd / 2 ba / 1,442 sq ft · 8168 BOAT HOOK LOOP #303
- $375,000 · 4 bd / 2.5 ba / 1,640 sq ft · 13730 LENSDALE LANE (Southbridge Village)
- $399,000 · 3 bd / 2.5 ba / 1,651 sq ft · 14077 ANCILLA BOULEVARD
$400K – $500K: 29 homes
- $409,900 · 3 bd / 2.5 ba / 1,547 sq ft · 8860 HERENCIA ALLEY
- $445,000 · 3 bd / 2.5 ba / 1,748 sq ft · 13048 GARRIDAN AVENUE (Windermere Sound)
- $450,000 · 2 bd / 1 ba / 1,216 sq ft · 9764 GOTHA ROAD (Gotha Town)
- $495,000 · 4 bd / 2.5 ba / 1,866 sq ft · 7668 FAIRGROVE AVENUE (Windermere Sound)
$500K – $750K: 61 homes
- $529,000 · 3 bd / 2 ba / 2,085 sq ft · 4844 FLINT ROAD (Summerport)
- $539,900 · 4 bd / 2.5 ba / 2,074 sq ft · 11938 SILVERLAKE PARK DRIVE (Windermere Trails)
- $550,000 · 5 bd / 3.5 ba / 2,268 sq ft · 9021 VIA DI CANTI (Royal Estates)
- $556,256 · 3 bd / 2.5 ba / 1,649 sq ft · 13321 LUSH LIME ALLEY (Lake Cawood Cove)
$750K – $1M: 26 homes
- $969,000 · 5 bd / 4.5 ba / 3,797 sq ft · 9609 WESTOVER CLUB CIRCLE
- $870,000 · 4 bd / 3 ba / 3,746 sq ft · 9043 HORIZON POINTE TRAIL (Windermere Trails)
- $759,000 · 4 bd / 3.5 ba / 2,886 sq ft · 8104 JAILENE DRIVE
- $760,000 · 5 bd / 3.5 ba / 3,705 sq ft · 12832 WESTSIDE VILLAGE LOOP
$1M and up: 122 homes
- $1.29M · 5 bd / 4 ba / 3,358 sq ft · 11524 CLAYMONT CIRCLE (Keene’s Pointe)
- $1.50M · 5 bd / 4.5 ba / 4,238 sq ft · 6239 RYDAL COURT
- $12.35M · 7 bd / 9.5 ba / 11,465 sq ft · 9312 BLANCHE COVE DR (Isleworth 5Th Amd)
- $1.19M · 4 bd / 3.5 ba / 2,665 sq ft · 12989 WESTSIDE VILLAGE LOOP (Westside Village)
Homes for sale in Windermere by ZIP code
Where the inventory is: active listings and the median asking price by ZIP. ZIPs link to their housing scorecard.
| ZIP | Homes for sale | Median list price |
|---|---|---|
| 34786 | 161 | $1.07M |
Windermere communities with the most homes for sale
The Windermere neighborhoods and subdivisions with active listings, the median asking price in each, and what homes there actually sold for over the last 12 months. Community names open the community guide with live inventory, sales history, HOA and schools.
| Community | For sale | Median list | Median sold (12 mo) | Days on market |
|---|---|---|---|---|
| Keene’s Pointe | 14 | $2.02M | — | — |
| Windermere Trails | 12 | $652,500 | — | — |
| Summerport | 6 | $689,950 | — | — |
| Gotha Town | 6 | $1.42M | — | — |
| Lake Burden South Ph I | 6 | $449,000 | — | — |
| Silver Woods | 5 | $584,900 | — | — |
| Windermere Isle | 5 | $1.03M | — | — |
| Windermere Sound | 5 | $495,000 | — | — |
| Town of Windermere | 5 | $1.90M | — | — |
| Westside Village | 4 | $1.06M | — | — |
| Casa Del Lago | 4 | $2.35M | — | — |
| Casabella | 4 | $3.65M | — | — |
| Palms At Windermere | 3 | $1.02M | — | — |
| Reserve At Lake Butler Sound | 3 | $1.55M | — | — |
| Carrington | 3 | $450,000 | — | — |
| Lake Butler Estates | 3 | $1.77M | — | — |
| Lakes Windermere | 3 | $609,900 | — | — |
| Weatherstone On Lake Olivia | 2 | $2.52M | — | — |
| Windsor Hill | 2 | $1.41M | — | — |
| Balmoral | 2 | $1.62M | — | — |
| Bellaria | 2 | $3.00M | — | — |
| Belmere Village G2 48 65 | 2 | $735,000 | — | — |
| Enclave | 2 | $1.41M | — | — |
| Lake Cawood Cove | 2 | $598,968 | — | — |
| Lakes/Windermere-Lk Reams Twhm | 2 | $379,500 | — | — |
| Lakeside/Lks/Windermere | 2 | $310,000 | — | — |
| Oasis Cove Ii/Lakeside Village Ph | 1 | $399,999 | — | — |
| Oxford Moor 47/30 | 1 | $1.55M | — | — |
| Peachtree Park | 1 | $829,500 | — | — |
| Preston Square | 1 | $575,000 | — | — |
What is for sale in Windermere: property types
- Single-family homes: 210
- Townhouses: 43
- Condos: 8
Browse by type: Condos for sale in Windermere (8) · Townhomes for sale in Windermere (43).
The Windermere housing market right now
Over the last 12 months 440 homes sold in Windermere at a median of $640,000 (-1.9% year over year), $274 per square foot. Sellers received 95% of list price and homes took a median 40 days to go under contract. With 261 homes for sale against that sales pace, months of supply is 7.1, a buyer’s market by the six-month rule. Cash buyers accounted for 32% of sales. New construction was 5% of sales.
Windermere supply by price band
| Price band | Active | Sold, 12 mo | Months of supply | DOM |
|---|---|---|---|---|
| $300K–$500K | 13 | 71 | 2.2 | 52 |
| $500K–$750K | 39 | 150 | 3.1 | 34 |
| $750K+ | 74 | 219 | 4.1 | 53 |
Windermere home prices by year
Median sold price, closed sales, days on market and sale-to-list ratio by year, from Momentum’s MLS record.
| Year | Median sold price | Homes sold | Days on market | Sale-to-list |
|---|---|---|---|---|
| 2019 | $700,031 | 96 | 87 | 93% |
| 2021 | $838,405 | 82 | 17 | 98% |
| 2022 | $756,944 | 1,051 | 9 | 100% |
| 2023 | $861,251 | 253 | 21 | 96% |
| 2024 | $1.03M | 684 | 23 | 96% |
| 2025 | $992,016 | 727 | 45 | 95% |
| 2026 | $996,057 | 711 | 41 | 95% |
What a home in Windermere costs to own
Take the median $930,000 listing with 20% down at today’s 6.71% 30-year rate: principal and interest run about $4,806/month. Orange County’s typical millage of 16.67 puts property tax near $14,673/year after the $50,000 homestead exemption — and that is the reset bill a buyer pays, not the seller’s capped one. Citizens’ average premium in Orange County is about $1,409/year; newer roofs and inland addresses usually quote below it. All in, plan on roughly $6,146/month plus any HOA or CDD assessment.
Explore Windermere
- All homes for sale in Orange County, FL
- Windermere market intelligence: prices, supply and trends
- Moving to Windermere: the data guide
- Cost of living in Windermere
- New construction homes in Windermere
- Best neighborhoods in Windermere
- Orange County property tax guide
- Search every Windermere community
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Common questions
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Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Windermere as of 2026-09-06 and refresh as homes list and sell. Listings courtesy of Stellar MLS as distributed by MLS GRID. The data relating to real estate for sale on this page comes in part from the Internet Data Exchange (IDX) program of the MLS(s) named above; listings held by brokerages other than Momentum Realty are marked with the listing brokerage’s name. Information is deemed reliable but not guaranteed. Estimates are not guarantees. Equal Housing Opportunity.