Windermere, FL Price Reductions
A price reduction is the clearest signal a seller sends: the first number did not work. This tracker lists every Windermere listing that lowered its asking price, updated nightly from the live MLS record — the old price, the new price, the size of the cut and how long the home has been on the market — so buyers can see where sellers are moving and sellers can see what their competition just did.
16 homes for sale in Windermere, FL cut their asking price in the last 7 days and 60 in the last 30, out of 230 active listings (22% reduced at least once this month). The median reduction is 3.0% ($30,500). The largest cut this week was $2,000,000 on 9621 Windy Ridge Road in Orange County ($8,999,999 → $6,999,999).
Latest price reductions in Windermere
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 12102 Montalcino Circle Nov 4 · 4 bd · 4.5 ba · 4,296 sf | Casa Del Lago | $3,100,000 | $2,900,000 | −6.5% | 85 |
| 7720 Ficquette Road Nov 4 · 6 bd · 4.5 ba · 4,282 sf | Lake Hancock Shores | $2,999,996 | $2,800,000 | −6.7% | 90 |
| 1700 Lake Roberts Court Nov 3 · 5 bd · 4 ba · 3,929 sf | Butler Bay Windermere Club | $1,350,000 | $1,299,900 | −3.7% | 144 |
| 11113 Lake Butler Boulevard Nov 1 · 5 bd · 5.5 ba · 4,094 sf | Wauseon Ridge | $2,150,000 | $2,050,000 | −4.7% | 76 |
| 12417 Montalcino Circle Nov 1 · 4 bd · 3.5 ba · 3,166 sf | Casa Del Lago | $1,595,000 | $1,495,000 | −6.3% | 97 |
| 9621 Windy Ridge Road Oct 29 · 9 bd · 13 ba · 20,445 sf | Orange County | $8,999,999 | $6,999,999 | −22.2% | 11 |
| 13596 Gorgona Isle Drive Oct 29 · 6 bd · 4.5 ba · 3,794 sf | windermere isle | $1,396,000 | $1,296,000 | −7.2% | 289 |
| 101 Lee Street Oct 29 · 5 bd · 4 ba · 4,186 sf | Windermere Town | $1,395,000 | $1,300,000 | −6.8% | 47 |
| 14213 Crest Palm Avenue Oct 29 · 6 bd · 4.5 ba · 4,564 sf | Palms At Windermere | $1,289,770 | $1,204,990 | −6.6% | 65 |
| 4282 Mckinnon Road Oct 29 · 6 bd · 6 ba · 5,869 sf | — | $1,895,000 | $1,845,000 | −2.6% | 82 |
| 5145 Latrobe Drive Oct 29 · 4 bd · 4.5 ba · 4,512 sf | Isleworth | $2,949,000 | $2,899,000 | −1.7% | 259 |
| 2540 Hempel Cove Ct Oct 29 · 5 bd · 3 ba · 3,356 sf | Lake Down Cove | $1,325,000 | $1,299,000 | −2.0% | 62 |
| 8576 Powder Ridge Trail Oct 29 · 4 bd · 3.5 ba · 2,661 sf | windermere trails | $620,000 | $597,000 | −3.7% | 25 |
| 7752 Rigby Street Oct 29 · 3 bd · 2.5 ba · 1,335 sf | — | $395,000 | $385,000 | −2.5% | 90 |
| 8168 Boat Hook Loop #302 Oct 29 · 2 bd · 2 ba · 1,161 sf | lakeside lakes windermere windermere | $299,997 | $297,997 | −0.7% | 26 |
| 8630 Powder Ridge Trail Oct 29 · 3 bd · 2.5 ba · 1,853 sf | windermere trails | $528,000 | $527,500 | −0.1% | 79 |
| 713 Main Street Oct 24 · 6 bd · 5 ba · 5,031 sf | — | $2,099,000 | $1,999,000 | −4.8% | 318 |
| 2009 Woody Drive Oct 24 · 4 bd · 3 ba · 3,540 sf | Windermere Downs | $1,150,000 | $1,125,000 | −2.2% | 117 |
| 2540 Hempel Cove Ct Oct 24 · 5 bd · 3 ba · 3,356 sf | Lake Down Cove | $1,349,900 | $1,325,000 | −1.8% | 62 |
| 12411 Montalcino Circle Oct 24 · 4 bd · 4.5 ba · 3,399 sf | Casa Del Lago | $1,395,000 | $1,375,000 | −1.4% | 198 |
| 12333 Via Derna Place Oct 24 · 3 bd · 2.5 ba · 1,919 sf | Carrington | $449,000 | $445,000 | −0.9% | 52 |
| 4226 Downeast Lane Oct 23 · 5 bd · 3 ba · 5,316 sf | Orange County | $9,750,000 | $9,250,000 | −5.1% | 374 |
| 11113 Lake Butler Boulevard Oct 23 · 5 bd · 5.5 ba · 4,094 sf | Wauseon Ridge | $2,299,000 | $2,150,000 | −6.5% | 76 |
| 6055 Louise Cove Drive Oct 23 · 5 bd · 5.5 ba · 7,158 sf | Orange County | $6,900,000 | $6,850,000 | −0.7% | 86 |
| 14353 Crest Palm Avenue Oct 23 · 4 bd · 3 ba · 2,740 sf | Palms At Windermere | $959,990 | $919,990 | −4.2% | 165 |
| 12785 Westside Village Loop Oct 23 · 4 bd · 3.5 ba · 2,996 sf | Westside Village | $799,000 | $769,000 | −3.8% | 27 |
| 9764 Gotha Road Oct 23 · 2 bd · 1 ba · 1,216 sf | Gotha Town | $450,000 | $425,000 | −5.6% | 59 |
| 212 W 1St Avenue Oct 23 · 4 bd · 2 ba · 2,627 sf | Windermere Town | $1,498,000 | $1,488,000 | −0.7% | 84 |
| 14371 Crest Palm Avenue Oct 23 · 4 bd · 4 ba · 3,153 sf | Palms At Windermere | $949,990 | $939,990 | −1.1% | 202 |
| 7712 Fordson Lane Oct 23 · 3 bd · 2.5 ba · 1,644 sf | — | $350,000 | $345,000 | −1.4% | 95 |
| 7430 Bentonshire Avenue Oct 23 · 2 bd · 2.5 ba · 1,412 sf | Wickham Park | $354,900 | $354,000 | −0.3% | 68 |
| 13622 Darchance Road Oct 20 · 3 bd · 2 ba · 2,147 sf | Enclave Berkshire Park B G H | $629,900 | $598,900 | −4.9% | 226 |
| 11446 Jasper Kay Terrace #202 Oct 20 · 2 bd · 2 ba · 1,161 sf | lakeside lakes windermere windermere | $295,000 | $290,000 | −1.7% | 38 |
| 14213 Crest Palm Avenue Oct 19 · 6 bd · 4.5 ba · 4,564 sf | Palms At Windermere | $1,305,990 | $1,289,770 | −1.2% | 65 |
| 12909 Cragside Lane Oct 19 · 4 bd · 2.5 ba · 2,460 sf | lakes windermere windermere | $639,500 | $625,000 | −2.3% | 52 |
| 2503 Butler Bay Drive Oct 18 · 4 bd · 3 ba · 3,297 sf | Butler Bay | $1,750,000 | $1,725,000 | −1.4% | 152 |
| 8860 Herencia Alley Oct 18 · 3 bd · 2.5 ba · 1,547 sf | — | $409,900 | $398,000 | −2.9% | 80 |
| 6288 Blakeford Drive Oct 16 · 5 bd · 5.5 ba · 5,366 sf | Keenes Pointe | $2,474,000 | $2,350,000 | −5.0% | 145 |
| 12353 Via Derna Place Oct 16 · 3 bd · 2.5 ba · 1,974 sf | Carrington | $460,000 | $445,900 | −3.1% | 217 |
| 11938 Silverlake Park Drive Oct 16 · 4 bd · 2.5 ba · 2,074 sf | windermere trails | $519,900 | $510,000 | −1.9% | 91 |
| 12417 Cruxbury Drive Oct 16 · 2 bd · 2.5 ba · 1,311 sf | Lakes Windermere Lake Reams Twhm | $360,000 | $359,000 | −0.3% | 58 |
| 11532 Waterstone Loop Drive Oct 15 · 4 bd · 5 ba · 4,169 sf | Waterstone | $2,350,000 | $2,199,000 | −6.4% | 34 |
| 5070 Down Point Lane Oct 15 · 6 bd · 6.5 ba · 7,349 sf | Sunset Bay | $4,995,000 | $4,945,000 | −1.0% | 249 |
| 12640 Salomon Cove Drive Oct 15 · 5 bd · 3.5 ba · 3,694 sf | Westside Village | $1,270,000 | $1,220,000 | −3.9% | 198 |
| 1243 Dingens Avenue Oct 15 · 4 bd · 3 ba · 2,670 sf | Gotha Town | $990,000 | $950,000 | −4.0% | 73 |
| 11429 Brownstone Street Oct 15 · 4 bd · 2.5 ba · 1,910 sf | lake burden south | $439,000 | $429,000 | −2.3% | 111 |
| 14442 Desert Haven Street #4305 Oct 15 · 3 bd · 2.5 ba · 1,534 sf | Oasis Cove At Lakeside Village | $359,900 | $359,000 | −0.3% | 147 |
| 8241 Tibet Butler Drive Oct 14 · 4 bd · 3.5 ba · 3,680 sf | Keenes Pointe | $1,740,000 | $1,699,000 | −2.4% | 83 |
| 7752 Rigby Street Oct 14 · 3 bd · 2.5 ba · 1,335 sf | — | $399,000 | $395,000 | −1.0% | 90 |
| 1480 Hempel Avenue Oct 13 · 5 bd · 4.5 ba · 4,219 sf | Gotha Town | $1,695,000 | $1,598,000 | −5.7% | 73 |
| 800 W 2Nd Avenue Oct 10 · 5 bd · 4.5 ba · 5,511 sf | Orange County | $5,999,000 | $5,600,000 | −6.7% | 102 |
| 9609 Westover Club Circle Oct 10 · 5 bd · 4.5 ba · 3,797 sf | — | $969,000 | $939,000 | −3.1% | 74 |
| 14371 Crest Palm Avenue Oct 9 · 4 bd · 4 ba · 3,153 sf | Palms At Windermere | $989,990 | $949,990 | −4.0% | 202 |
| 2128 Lake Crescent Court Oct 9 · 4 bd · 2 ba · 2,987 sf | Butler Bay | $751,400 | $713,840 | −5.0% | 147 |
| 14341 Crest Palm Avenue Oct 9 · 4 bd · 4 ba · 3,153 sf | Palms At Windermere | $1,090,990 | $1,070,990 | −1.8% | 146 |
| 14353 Crest Palm Avenue Oct 9 · 4 bd · 3 ba · 2,740 sf | Palms At Windermere | $979,990 | $959,990 | −2.0% | 165 |
| 212 W 1St Avenue Oct 9 · 4 bd · 2 ba · 2,627 sf | Windermere Town | $1,499,000 | $1,498,000 | −0.1% | 84 |
| 7720 Ficquette Road Oct 7 · 6 bd · 4.5 ba · 4,282 sf | Lake Hancock Shores | $3,100,000 | $2,999,996 | −3.2% | 90 |
| 212 W 1St Avenue Oct 6 · 4 bd · 2 ba · 2,627 sf | Windermere Town | $1,599,000 | $1,499,000 | −6.3% | 84 |
| 13317 Lush Lime Alley Oct 6 · 3 bd · 2.5 ba · 1,699 sf | LAKE CAWOOD Cove | $586,846 | $549,990 | −6.3% | 41 |
Biggest cuts this week
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 9621 Windy Ridge Road Oct 29 · 9 bd · 13 ba · 20,445 sf | Orange County | $8,999,999 | $6,999,999 | −22.2% | 11 |
| 12102 Montalcino Circle Nov 4 · 4 bd · 4.5 ba · 4,296 sf | Casa Del Lago | $3,100,000 | $2,900,000 | −6.5% | 85 |
| 7720 Ficquette Road Nov 4 · 6 bd · 4.5 ba · 4,282 sf | Lake Hancock Shores | $2,999,996 | $2,800,000 | −6.7% | 90 |
| 11113 Lake Butler Boulevard Nov 1 · 5 bd · 5.5 ba · 4,094 sf | Wauseon Ridge | $2,150,000 | $2,050,000 | −4.7% | 76 |
| 13596 Gorgona Isle Drive Oct 29 · 6 bd · 4.5 ba · 3,794 sf | windermere isle | $1,396,000 | $1,296,000 | −7.2% | 289 |
| 12417 Montalcino Circle Nov 1 · 4 bd · 3.5 ba · 3,166 sf | Casa Del Lago | $1,595,000 | $1,495,000 | −6.3% | 97 |
| 101 Lee Street Oct 29 · 5 bd · 4 ba · 4,186 sf | Windermere Town | $1,395,000 | $1,300,000 | −6.8% | 47 |
| 14213 Crest Palm Avenue Oct 29 · 6 bd · 4.5 ba · 4,564 sf | Palms At Windermere | $1,289,770 | $1,204,990 | −6.6% | 65 |
| 1700 Lake Roberts Court Nov 3 · 5 bd · 4 ba · 3,929 sf | Butler Bay Windermere Club | $1,350,000 | $1,299,900 | −3.7% | 144 |
| 4282 Mckinnon Road Oct 29 · 6 bd · 6 ba · 5,869 sf | — | $1,895,000 | $1,845,000 | −2.6% | 82 |
Communities with the most reductions (30 days)
| Community | City | Reductions | Median cut |
|---|---|---|---|
| Palms At Windermere | Windermere | 7 | −2.0% |
| Orange County | Windermere | 4 | −5.9% |
| Windermere Town | Windermere | 4 | −3.5% |
| windermere trails | Windermere | 3 | −1.9% |
| Gotha Town | Windermere | 3 | −5.6% |
| Casa Del Lago | Windermere | 3 | −6.3% |
| Westside Village | Windermere | 2 | −3.8% |
| Lake Hancock Shores | Windermere | 2 | −4.9% |
| Lake Down Cove | Windermere | 2 | −1.9% |
| Wauseon Ridge | Windermere | 2 | −5.6% |
| lakeside lakes windermere windermere | Windermere | 2 | −1.2% |
| Butler Bay | Windermere | 2 | −3.2% |
| Carrington | Windermere | 2 | −2.0% |
| Keenes Pointe | Windermere | 2 | −3.7% |
How to read this
Reductions are detected by comparing each listing’s asking price night over night in the MLS feed; a listing appears once per cut, and the share reduced counts each listing once. Relists at a new price under a new MLS number are not matched. Prices are asking prices. Source: live MLS feeds compiled by Momentum Research, updated November 5, 2026.