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.
14 homes for sale in Windermere, FL cut their asking price in the last 7 days and 14 in the last 30, out of 176 active listings (8% reduced at least once this month). The median reduction is 2.3% ($37,000). The largest cut this week was $105,000 on 9648 Weatherstone Court in Weatherstone On Lake Olivia ($2,395,000 → $2,290,000).
Latest price reductions in Windermere
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 9061 Ron Den Lane Sep 17 · 5 bd · 6 ba · 6,300 sf | Down Acres Estates | $6,900,000 | $6,800,000 | −1.4% | 91 |
| 9648 Weatherstone Court Sep 16 · 6 bd · 4 ba · 4,482 sf | Weatherstone On Lake Olivia | $2,395,000 | $2,290,000 | −4.4% | 148 |
| 13542 Gorgona Isle Drive Sep 16 · 4 bd · 3 ba · 2,224 sf | windermere isle | $879,000 | $850,000 | −3.3% | 186 |
| 8386 Iron Mountain Trail Sep 16 · 3 bd · 2.5 ba · 1,631 sf | windermere trails | $475,000 | $460,000 | −3.2% | 50 |
| 5413 Walsh Pond Court Sep 16 · 4 bd · 3.5 ba · 3,124 sf | summerport | $795,000 | $780,000 | −1.9% | 153 |
| 7668 Fairgrove Avenue Sep 16 · 4 bd · 2.5 ba · 1,866 sf | windermere sound | $495,000 | $485,000 | −2.0% | 36 |
| 8701 Iron Mountain Trail Sep 16 · 6 bd · 4.5 ba · 4,507 sf | windermere trails | $999,000 | $998,999 | −0.0% | 22 |
| 11113 Lake Butler Boulevard Sep 15 · 5 bd · 5.5 ba · 4,094 sf | Wauseon Ridge | $2,395,000 | $2,299,000 | −4.0% | 27 |
| 9548 Crown Prince Lane Sep 15 · 4 bd · 4 ba · 3,997 sf | Windsor Hill | $1,450,000 | $1,395,000 | −3.8% | 111 |
| 8241 Tibet Butler Drive Sep 15 · 4 bd · 3.5 ba · 3,680 sf | Keenes Pointe | $1,785,000 | $1,740,000 | −2.5% | 35 |
| 4844 Flint Road Sep 15 · 3 bd · 2 ba · 2,085 sf | summerport | $529,000 | $519,000 | −1.9% | 17 |
| 9575 Westover Roberts Road Sep 14 · 7 bd · 8 ba · 8,931 sf | Gotha Town | $4,850,000 | $4,750,000 | −2.1% | 307 |
| 212 W 1St Avenue Sep 14 · 4 bd · 2 ba · 2,627 sf | Windermere Town | $1,650,000 | $1,600,000 | −3.0% | 35 |
| 13519 Bicton Lane Sep 14 · 4 bd · 3.5 ba · 2,594 sf | Lakes Windermere Peachtree | $695,000 | $689,000 | −0.9% | 248 |
Biggest cuts this week
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 9648 Weatherstone Court Sep 16 · 6 bd · 4 ba · 4,482 sf | Weatherstone On Lake Olivia | $2,395,000 | $2,290,000 | −4.4% | 148 |
| 9061 Ron Den Lane Sep 17 · 5 bd · 6 ba · 6,300 sf | Down Acres Estates | $6,900,000 | $6,800,000 | −1.4% | 91 |
| 9575 Westover Roberts Road Sep 14 · 7 bd · 8 ba · 8,931 sf | Gotha Town | $4,850,000 | $4,750,000 | −2.1% | 307 |
| 11113 Lake Butler Boulevard Sep 15 · 5 bd · 5.5 ba · 4,094 sf | Wauseon Ridge | $2,395,000 | $2,299,000 | −4.0% | 27 |
| 9548 Crown Prince Lane Sep 15 · 4 bd · 4 ba · 3,997 sf | Windsor Hill | $1,450,000 | $1,395,000 | −3.8% | 111 |
| 212 W 1St Avenue Sep 14 · 4 bd · 2 ba · 2,627 sf | Windermere Town | $1,650,000 | $1,600,000 | −3.0% | 35 |
| 8241 Tibet Butler Drive Sep 15 · 4 bd · 3.5 ba · 3,680 sf | Keenes Pointe | $1,785,000 | $1,740,000 | −2.5% | 35 |
| 13542 Gorgona Isle Drive Sep 16 · 4 bd · 3 ba · 2,224 sf | windermere isle | $879,000 | $850,000 | −3.3% | 186 |
| 8386 Iron Mountain Trail Sep 16 · 3 bd · 2.5 ba · 1,631 sf | windermere trails | $475,000 | $460,000 | −3.2% | 50 |
| 5413 Walsh Pond Court Sep 16 · 4 bd · 3.5 ba · 3,124 sf | summerport | $795,000 | $780,000 | −1.9% | 153 |
Communities with the most reductions (30 days)
| Community | City | Reductions | Median cut |
|---|---|---|---|
| windermere trails | Windermere | 2 | −1.6% |
| summerport | Windermere | 2 | −1.9% |
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 September 17, 2026.