Winter Park, FL Price Reductions
A price reduction is the clearest signal a seller sends: the first number did not work. This tracker lists every Winter Park 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.
12 homes for sale in Winter Park, FL cut their asking price in the last 7 days and 12 in the last 30, out of 228 active listings (5% reduced at least once this month). The median reduction is 2.5% ($12,500). The largest cut this week was $100,000 on 462 W Lyman Avenue in Winter Park Villas ($1,595,000 → $1,495,000).
Latest price reductions in Winter Park
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 341 E Reading Way Sep 17 · 4 bd · 4 ba · 3,723 sf | Charmont | $1,565,000 | $1,525,000 | −2.6% | 78 |
| 1250 Formosa Avenue Sep 17 · 3 bd · 3.5 ba · 1,937 sf | Urban Green | $550,000 | $535,000 | −2.7% | 105 |
| 151 N Orlando Avenue #261 Sep 17 · 1 bd · 1 ba · 582 sf | Lake Killarney Condo | $229,999 | $219,999 | −4.3% | 27 |
| 722 S Ranger Boulevard Sep 17 · 4 bd · 3 ba · 2,164 sf | winter park pines | $778,999 | $775,000 | −0.5% | 69 |
| 462 W Lyman Avenue Sep 16 · 3 bd · 2.5 ba · 1,944 sf | Winter Park Villas | $1,595,000 | $1,495,000 | −6.3% | 65 |
| 207 E Kings Way Sep 16 · 5 bd · 4.5 ba · 3,719 sf | Charmont | $3,650,000 | $3,600,000 | −1.4% | 358 |
| 1652 Berkshire Avenue Sep 16 · 3 bd · 2 ba · 1,498 sf | Orwin Manor Westminster | $499,000 | $479,000 | −4.0% | 33 |
| 1120 Wisconsin Avenue Sep 15 · 3 bd · 3.5 ba · 2,213 sf | Henkel | $1,025,000 | $999,000 | −2.5% | 104 |
| 1500 Gay Road #4D Sep 14 · 1 bd · 1 ba · 732 sf | Chateaux Du Lac | $169,900 | $164,500 | −3.2% | 61 |
| 3019 Antique Oaks Circle #127 Sep 14 · 1 bd · 1 ba · 749 sf | Parkview Village | $144,500 | $143,500 | −0.7% | 26 |
| 1695 Lee Road #D211 Sep 14 · 2 bd · 1 ba · 881 sf | waterfall cove winter park winter park | $108,000 | $107,000 | −0.9% | 123 |
| 2500 Lee Rd. #222 Sep 14 · 1 bd · 1 ba · 645 sf | Lakeside Manor Apartments Condo | $184,900 | $184,400 | −0.3% | 257 |
Biggest cuts this week
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 462 W Lyman Avenue Sep 16 · 3 bd · 2.5 ba · 1,944 sf | Winter Park Villas | $1,595,000 | $1,495,000 | −6.3% | 65 |
| 207 E Kings Way Sep 16 · 5 bd · 4.5 ba · 3,719 sf | Charmont | $3,650,000 | $3,600,000 | −1.4% | 358 |
| 341 E Reading Way Sep 17 · 4 bd · 4 ba · 3,723 sf | Charmont | $1,565,000 | $1,525,000 | −2.6% | 78 |
| 1120 Wisconsin Avenue Sep 15 · 3 bd · 3.5 ba · 2,213 sf | Henkel | $1,025,000 | $999,000 | −2.5% | 104 |
| 1652 Berkshire Avenue Sep 16 · 3 bd · 2 ba · 1,498 sf | Orwin Manor Westminster | $499,000 | $479,000 | −4.0% | 33 |
| 1250 Formosa Avenue Sep 17 · 3 bd · 3.5 ba · 1,937 sf | Urban Green | $550,000 | $535,000 | −2.7% | 105 |
| 151 N Orlando Avenue #261 Sep 17 · 1 bd · 1 ba · 582 sf | Lake Killarney Condo | $229,999 | $219,999 | −4.3% | 27 |
| 1500 Gay Road #4D Sep 14 · 1 bd · 1 ba · 732 sf | Chateaux Du Lac | $169,900 | $164,500 | −3.2% | 61 |
| 722 S Ranger Boulevard Sep 17 · 4 bd · 3 ba · 2,164 sf | winter park pines | $778,999 | $775,000 | −0.5% | 69 |
| 3019 Antique Oaks Circle #127 Sep 14 · 1 bd · 1 ba · 749 sf | Parkview Village | $144,500 | $143,500 | −0.7% | 26 |
Communities with the most reductions (30 days)
| Community | City | Reductions | Median cut |
|---|---|---|---|
| Charmont | Winter Park | 2 | −2.0% |
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.