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.
19 homes for sale in Winter Park, FL cut their asking price in the last 7 days and 104 in the last 30, out of 325 active listings (27% reduced at least once this month). The median reduction is 3.0% ($20,000). The largest cut this week was $140,000 on 1951 Winter Park Road in Charmont ($2,089,000 → $1,949,000).
Latest price reductions in Winter Park
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 1320 Gladiolas Dr Nov 6 · 4 bd · 2 ba · 1,624 sf | — | $459,900 | $449,000 | −2.4% | 160 |
| 1448 Lake Florence Way Nov 4 · 5 bd · 4.5 ba · 3,652 sf | — | $1,049,900 | $999,900 | −4.8% | 160 |
| 2572 Fifeshire Drive Nov 4 · 4 bd · 2.5 ba · 2,578 sf | — | $899,900 | $875,000 | −2.8% | 46 |
| 2275 Island Run Nov 4 · 3 bd · 2 ba · 1,467 sf | — | $299,990 | $279,999 | −6.7% | 57 |
| 7384 Grand Avenue Nov 3 · 3 bd · 2 ba · 1,162 sf | — | $415,000 | $385,000 | −7.2% | 77 |
| 700 Melrose Avenue #M23 Nov 3 · 2 bd · 2 ba · 1,074 sf | Winter Park Gardens Condo | $354,000 | $340,000 | −4.0% | 25 |
| 5184 Lazy Oaks Drive Nov 3 · 2 bd · 2 ba · 1,008 sf | Lazy Oaks Condo | $275,000 | $268,000 | −2.5% | 121 |
| 1951 Winter Park Road Nov 1 · 4 bd · 3.5 ba · 3,479 sf | Charmont | $2,089,000 | $1,949,000 | −6.7% | 39 |
| 2067 Poinciana Road Nov 1 · 4 bd · 2 ba · 2,352 sf | — | $560,000 | $548,000 | −2.1% | 28 |
| 2500 Lee Road #123 Nov 1 · 1 bd · 1 ba · 645 sf | Lakeside Manor Apartments Condo | $169,900 | $159,900 | −5.9% | 31 |
| 1407 Broad Wing Lane Nov 1 · 3 bd · 2.5 ba · 2,308 sf | — | $491,000 | $482,000 | −1.8% | 20 |
| 1000 S Semoran Boulevard #302 Nov 1 · 1 bd · 1 ba · 796 sf | Golfside Villas Condo | $105,000 | $97,000 | −7.6% | 95 |
| 7560 Aloma Pines Court Oct 31 · 3 bd · 2.5 ba · 1,866 sf | — | $355,000 | $325,000 | −8.5% | 32 |
| 7525 Lodge Pole Trail Oct 31 · 4 bd · 2 ba · 1,936 sf | arrowhead cove | $575,000 | $550,000 | −4.3% | 74 |
| 1660 Gladiolas Drive Oct 31 · 3 bd · 2 ba · 2,047 sf | — | $479,900 | $469,900 | −2.1% | 75 |
| 1287 Verdant Glade Place Oct 31 · 4 bd · 3.5 ba · 3,020 sf | — | $745,000 | $735,000 | −1.3% | 54 |
| 1535 Lawndale Circle Oct 31 · 3 bd · 2 ba · 1,676 sf | — | $420,000 | $415,000 | −1.2% | 144 |
| 1306 S Pennsylvania Avenue #5 Oct 31 · 2 bd · 1 ba · 830 sf | Virginia Heights | $349,000 | $347,500 | −0.4% | 36 |
| 7530 Cranes Creek Court Oct 31 · 3 bd · 2.5 ba · 1,545 sf | — | $307,900 | $306,900 | −0.3% | 63 |
| 901 Golfview Terrace Oct 29 · 5 bd · 5.5 ba · 5,479 sf | Orange County | $6,995,000 | $6,795,000 | −2.9% | 45 |
| 698 N New York Avenue Oct 29 · 5 bd · 5.5 ba · 5,096 sf | Orange County | $6,195,000 | $5,995,000 | −3.2% | 39 |
| 231 Chelton Circle Oct 29 · 4 bd · 6 ba · 5,550 sf | Orange County | $4,700,000 | $4,500,000 | −4.3% | 145 |
| 125 S Interlachen Avenue #1 Oct 29 · 3 bd · 4 ba · 3,878 sf | Orange County | $3,695,000 | $3,645,000 | −1.4% | 92 |
| 462 W Lyman Avenue Oct 29 · 3 bd · 2.5 ba · 1,944 sf | Winter Park Villas | $1,495,000 | $1,450,000 | −3.0% | 112 |
| 1621 Chestnut Avenue Oct 29 · 3 bd · 2.5 ba · 2,022 sf | Lake Knowles Terrace | $879,000 | $845,000 | −3.9% | 65 |
| 7348 Grand Avenue Oct 29 · 3 bd · 2 ba · 1,509 sf | — | $285,000 | $255,000 | −10.5% | 41 |
| 311 E Morse Boulevard #4-5 Oct 29 · 2 bd · 2 ba · 1,763 sf | Phillips Circle | $925,000 | $895,000 | −3.2% | 48 |
| 1660 Orange Avenue Oct 29 · 3 bd · 2 ba · 1,614 sf | Orwin Manor Westminster | $479,900 | $449,900 | −6.3% | 39 |
| 330 Elkhorn Court Oct 29 · 3 bd · 2 ba · 1,570 sf | Winter Park Pines Merrie Oaks | $534,900 | $509,900 | −4.7% | 263 |
| 100 S Interlachen Avenue #401 Oct 29 · 3 bd · 2 ba · 1,639 sf | Cloisters Condo | $850,000 | $825,000 | −2.9% | 32 |
| 2207 Kindel Avenue Oct 29 · 3 bd · 2.5 ba · 2,733 sf | — | $1,600,000 | $1,575,000 | −1.6% | 67 |
| 471 Holt Avenue Oct 29 · 4 bd · 3 ba · 2,528 sf | Winter Park Villas | $950,000 | $925,000 | −2.6% | 64 |
| 508 Brechin Drive Oct 29 · 3 bd · 2 ba · 1,783 sf | Kenilworth Shores | $609,000 | $599,000 | −1.6% | 55 |
| 2020 Leanne Court Oct 29 · 4 bd · 3 ba · 2,088 sf | — | $479,900 | $469,900 | −2.1% | 25 |
| 630 Killarney Bay Court #3 Oct 29 · 2 bd · 2.5 ba · 1,428 sf | Killarney Bay Condo | $459,900 | $449,900 | −2.2% | 218 |
| 4260 Bear Gully Road Oct 29 · 4 bd · 3.5 ba · 2,322 sf | — | $594,000 | $585,000 | −1.5% | 41 |
| 2857 Clever Lane Oct 29 · 3 bd · 2.5 ba · 1,782 sf | — | $398,995 | $394,500 | −1.1% | 76 |
| 193 Lewfield Circle Oct 29 · 2 bd · 2.5 ba · 1,300 sf | Stratford A | $248,900 | $246,400 | −1.0% | 162 |
| 7530 Cranes Creek Court Oct 29 · 3 bd · 2.5 ba · 1,545 sf | — | $308,900 | $307,900 | −0.3% | 63 |
| 1441 Cardinal Court Oct 24 · 4 bd · 5.5 ba · 4,066 sf | Orange County | $3,995,000 | $3,600,000 | −9.9% | 200 |
| 1742 Temple Drive Oct 24 · 4 bd · 5 ba · 3,658 sf | Lake Knowles Terrace | $3,695,999 | $3,545,995 | −4.1% | 43 |
| 1821 Englewood Road Oct 24 · 5 bd · 5.5 ba · 3,863 sf | Forest Hills | $3,075,000 | $2,950,000 | −4.1% | 409 |
| 230 Killarney Drive Oct 24 · 4 bd · 1 ba · 1,260 sf | Killarney Estates | $1,250,000 | $1,150,000 | −8.0% | 108 |
| 240 Killarney Drive Oct 24 · 3 bd · 2.5 ba · 1,329 sf | Killarney Estates | $1,275,000 | $1,175,000 | −7.8% | 108 |
| 1271 Palmer Avenue Oct 24 · 4 bd · 4.5 ba · 2,850 sf | J Kronenberger | $2,195,000 | $2,125,000 | −3.2% | 47 |
| 150 E Reading Way Oct 24 · 3 bd · 2.5 ba · 2,080 sf | Charmont | $1,449,000 | $1,399,000 | −3.5% | 71 |
| 310 Granada Drive Oct 24 · 3 bd · 2 ba · 1,344 sf | Fairview Heights | $350,000 | $325,000 | −7.1% | 28 |
| 3020 Nicholson Drive Oct 24 · 4 bd · 2 ba · 1,756 sf | Wrenwood | $495,000 | $470,000 | −5.1% | 54 |
| 1652 Berkshire Avenue Oct 24 · 3 bd · 2 ba · 1,498 sf | Orwin Manor Westminster | $449,000 | $429,000 | −4.5% | 81 |
| 981 Aragon Avenue Oct 24 · 2 bd · 1 ba · 857 sf | Seville Park | $494,999 | $489,000 | −1.2% | 129 |
| 712 Baffie Avenue Oct 24 · 3 bd · 1 ba · 1,304 sf | Dubsdread Heights | $424,900 | $419,900 | −1.2% | 34 |
| 922 N Pennsylvania Avenue Oct 23 · 4 bd · 4 ba · 3,440 sf | — | $1,875,000 | $1,795,000 | −4.3% | 111 |
| 240 N Phelps Avenue Oct 23 · 5 bd · 4.5 ba · 2,889 sf | Sylvan Heights | $2,050,000 | $1,999,900 | −2.4% | 137 |
| 618 Blairshire Circle Oct 23 · 4 bd · 3 ba · 1,876 sf | Brookshire Heights | $895,000 | $875,000 | −2.2% | 50 |
| 7786 Fox Knoll Place Oct 23 · 3 bd · 2 ba · 1,301 sf | — | $410,500 | $398,000 | −3.0% | 36 |
| 5468 Bracken Court Oct 23 · 3 bd · 2.5 ba · 1,602 sf | — | $309,000 | $299,000 | −3.2% | 13 |
| 1003 Golfside Drive Oct 23 · 3 bd · 3 ba · 2,145 sf | — | $769,900 | $759,900 | −1.3% | 38 |
| 283 Sandlewood Trail #3 Oct 23 · 2 bd · 2.5 ba · 960 sf | — | $285,000 | $279,000 | −2.1% | 70 |
| 4260 Bear Gully Road Oct 23 · 4 bd · 3.5 ba · 2,322 sf | — | $599,000 | $594,000 | −0.8% | 41 |
| 5409 Albert Drive Oct 23 · 3 bd · 2 ba · 1,483 sf | — | $405,000 | $400,000 | −1.2% | 101 |
Biggest cuts this week
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 1951 Winter Park Road Nov 1 · 4 bd · 3.5 ba · 3,479 sf | Charmont | $2,089,000 | $1,949,000 | −6.7% | 39 |
| 1448 Lake Florence Way Nov 4 · 5 bd · 4.5 ba · 3,652 sf | — | $1,049,900 | $999,900 | −4.8% | 160 |
| 7560 Aloma Pines Court Oct 31 · 3 bd · 2.5 ba · 1,866 sf | — | $355,000 | $325,000 | −8.5% | 32 |
| 7384 Grand Avenue Nov 3 · 3 bd · 2 ba · 1,162 sf | — | $415,000 | $385,000 | −7.2% | 77 |
| 7525 Lodge Pole Trail Oct 31 · 4 bd · 2 ba · 1,936 sf | arrowhead cove | $575,000 | $550,000 | −4.3% | 74 |
| 2572 Fifeshire Drive Nov 4 · 4 bd · 2.5 ba · 2,578 sf | — | $899,900 | $875,000 | −2.8% | 46 |
| 2275 Island Run Nov 4 · 3 bd · 2 ba · 1,467 sf | — | $299,990 | $279,999 | −6.7% | 57 |
| 700 Melrose Avenue #M23 Nov 3 · 2 bd · 2 ba · 1,074 sf | Winter Park Gardens Condo | $354,000 | $340,000 | −4.0% | 25 |
| 2067 Poinciana Road Nov 1 · 4 bd · 2 ba · 2,352 sf | — | $560,000 | $548,000 | −2.1% | 28 |
| 1320 Gladiolas Dr Nov 6 · 4 bd · 2 ba · 1,624 sf | — | $459,900 | $449,000 | −2.4% | 160 |
Communities with the most reductions (30 days)
| Community | City | Reductions | Median cut |
|---|---|---|---|
| Orange County | Winter Park | 8 | −3.8% |
| Orwin Manor Westminster | Winter Park | 4 | −5.4% |
| Kenilworth Shores | Winter Park | 3 | −1.6% |
| Dubsdread Heights | Winter Park | 3 | −1.8% |
| Winter Park Pines Merrie Oaks | Winter Park | 2 | −2.8% |
| Killarney Estates | Winter Park | 2 | −7.9% |
| Park West Condo | Winter Park | 2 | −7.8% |
| Winter Park Village | Winter Park | 2 | −5.1% |
| Charmont | Winter Park | 2 | −5.1% |
| Virginia Heights | Winter Park | 2 | −1.6% |
| Lazy Oaks Condo | Winter Park | 2 | −3.9% |
| Winter Park Villas | Winter Park | 2 | −2.8% |
| Lake Knowles Terrace | Winter Park | 2 | −3.0% |
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 November 6, 2026.