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.
28 homes for sale in Winter Park, FL cut their asking price in the last 7 days and 93 in the last 30, out of 331 active listings (24% reduced at least once this month). The median reduction is 3.0% ($21,000). The largest cut this week was $200,000 on 125 S Interlachen Avenue #1 in Winter Park ($3,895,000 → $3,695,000).
Latest price reductions in Winter Park
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 560 Ololu Drive Oct 15 · 2 bd · 2 ba · 1,086 sf | Killarney Circle | $899,000 | $849,000 | −5.6% | 311 |
| 2430 Chantilly Avenue Oct 15 · 4 bd · 4 ba · 2,916 sf | Winter Park Village | $1,598,000 | $1,550,000 | −3.0% | 47 |
| 2017 Canny Cove Oct 15 · 3 bd · 2.5 ba · 1,907 sf | — | $379,999 | $379,998 | −0.0% | 71 |
| 702 Via Bella Oct 14 · 4 bd · 5.5 ba · 3,720 sf | Palmer Ave Lakeside Prop | $4,400,000 | $4,250,000 | −3.4% | 28 |
| 1404 Border Drive Oct 14 · 4 bd · 4 ba · 2,469 sf | Winter Park Village | $1,075,000 | $998,000 | −7.2% | 134 |
| 508 Brechin Drive Oct 14 · 3 bd · 2 ba · 1,783 sf | Kenilworth Shores | $629,000 | $609,000 | −3.2% | 36 |
| 811 Overspin Drive Oct 14 · 2 bd · 1 ba · 749 sf | Dubsdread Heights | $329,000 | $320,000 | −2.7% | 180 |
| 712 Baffie Avenue Oct 14 · 3 bd · 1 ba · 1,304 sf | Dubsdread Heights | $448,000 | $439,900 | −1.8% | 14 |
| 1955 Eland Avenue Oct 14 · 3 bd · 2 ba · 1,494 sf | Lake Bell Terrace | $410,000 | $405,000 | −1.2% | 61 |
| 1220 Howell Branch Road Oct 13 · 3 bd · 2 ba · 1,487 sf | — | $999,500 | $950,000 | −5.0% | 44 |
| 1517 Harmon Avenue Oct 13 · 4 bd · 3.5 ba · 2,135 sf | Lawndale | $1,095,000 | $1,049,000 | −4.2% | 24 |
| 1850 Bryan Avenue Oct 13 · 3 bd · 2 ba · 1,563 sf | lakeview terrace | $725,000 | $699,000 | −3.6% | 42 |
| 1660 Gladiolas Drive Oct 13 · 3 bd · 2 ba · 2,047 sf | — | $495,000 | $479,900 | −3.1% | 54 |
| 2041 Jewell Avenue Oct 13 · 3 bd · 1 ba · 1,508 sf | Pines | $439,900 | $430,000 | −2.3% | 95 |
| 1250 S Denning Dr #Unit 233 Oct 13 · 2 bd · 2 ba · 913 sf | Mead Garden | $245,000 | $242,500 | −1.0% | 49 |
| 125 S Interlachen Avenue #2 Oct 11 · 3 bd · 4 ba · 3,244 sf | — | $3,150,000 | $2,995,000 | −4.9% | 71 |
| 300 Carolina Avenue #402C Oct 11 · 3 bd · 2 ba · 1,350 sf | Park West Condo | $710,000 | $650,000 | −8.5% | 141 |
| 125 S Interlachen Avenue #1 Oct 10 · 3 bd · 4 ba · 3,878 sf | — | $3,895,000 | $3,695,000 | −5.1% | 68 |
| 3416 Arbutus Lane Oct 10 · 4 bd · 3 ba · 1,421 sf | Eastbrook | $395,000 | $379,900 | −3.8% | 1 |
| 5108 Lazy Oaks Drive #5108 Oct 10 · 2 bd · 2 ba · 1,008 sf | Lazy Oaks Condo | $269,000 | $255,000 | −5.2% | 39 |
| 330 Elkhorn Court Oct 10 · 3 bd · 2 ba · 1,570 sf | Winter Park Pines Merrie Oaks | $539,900 | $534,900 | −0.9% | 239 |
| 1741 Westchester Avenue Oct 10 · 3 bd · 2 ba · 1,434 sf | Orwin Manor Westminster | $529,000 | $524,900 | −0.8% | 158 |
| 2572 Fifeshire Drive Oct 9 · 4 bd · 2.5 ba · 2,578 sf | — | $925,000 | $899,900 | −2.7% | 22 |
| 1320 Gladiolas Dr Oct 9 · 4 bd · 2 ba · 1,624 sf | — | $469,900 | $459,900 | −2.1% | 135 |
| 1840 Aster Drive Oct 9 · 3 bd · 2 ba · 1,667 sf | — | $384,900 | $379,900 | −1.3% | 105 |
| 2008 Houndslake Drive Oct 9 · 4 bd · 2 ba · 2,250 sf | — | $475,000 | $470,000 | −1.1% | 115 |
| 1652 Berkshire Avenue Oct 8 · 3 bd · 2 ba · 1,498 sf | Orwin Manor Westminster | $479,000 | $449,000 | −6.3% | 59 |
| 2015 Summerfield Road Oct 8 · 4 bd · 4 ba · 3,024 sf | Kenilworth Shores | $1,262,500 | $1,250,000 | −1.0% | 118 |
| 2302 Barbados Drive Oct 7 · 2 bd · 2 ba · 1,544 sf | — | $295,000 | $275,000 | −6.8% | 33 |
| 1621 Chestnut Avenue Oct 7 · 3 bd · 2.5 ba · 2,022 sf | Lake Knowles Terrace | $899,000 | $879,000 | −2.2% | 43 |
| 1570 Palmer Avenue Oct 6 · 4 bd · 3.5 ba · 3,048 sf | Comstock Park | $1,595,000 | $1,495,000 | −6.3% | 133 |
| 443 Broadview Avenue Oct 6 · 4 bd · 3 ba · 2,803 sf | Killarney Estates | $1,095,000 | $999,000 | −8.8% | 26 |
| 1431 Palm Avenue Oct 6 · 2 bd · 2 ba · 1,540 sf | Lake Knowles Terrace | $825,000 | $799,999 | −3.0% | 53 |
| 3209 Heartwood Avenue Oct 6 · 4 bd · 2 ba · 1,627 sf | Bel Aire Pines | $449,900 | $439,900 | −2.2% | 12 |
| 2410 Sherbrooke Road Oct 5 · 4 bd · 2.5 ba · 2,141 sf | — | $789,000 | $769,000 | −2.5% | 31 |
| 2477 Tahoe Circle #2477 Oct 5 · 2 bd · 2 ba · 1,316 sf | — | $254,000 | $247,000 | −2.8% | 51 |
| 1840 Aster Drive Oct 5 · 3 bd · 2 ba · 1,667 sf | — | $389,950 | $384,900 | −1.3% | 105 |
| 4870 Seminole Avenue Oct 4 · 3 bd · 2 ba · 1,277 sf | Suburban Homes | $3,790,000 | $380,000 | −90.0% | 18 |
| 857 Brock Street Oct 4 · 5 bd · 5.5 ba · 4,827 sf | Park Grove | $4,650,000 | $4,350,000 | −6.5% | 53 |
| 723 Symonds Avenue Oct 4 · 4 bd · 4 ba · 3,065 sf | Horton Aaron | $1,700,000 | $1,600,000 | −5.9% | 131 |
| 2343 Versailles Avenue Oct 4 · 4 bd · 3.5 ba · 3,307 sf | Fontainebleau | $1,750,000 | $1,699,000 | −2.9% | 61 |
| 1257 Wading Waters Circle Oct 4 · 6 bd · 5 ba · 5,239 sf | Waters Edge At Hawks Crest | $1,600,000 | $1,550,000 | −3.1% | 22 |
| 2641 Carvell Court Oct 4 · 4 bd · 2 ba · 2,126 sf | Winter Park Estates | $550,000 | $525,000 | −4.5% | 60 |
| 1092 Eastbrook Boulevard Oct 4 · 3 bd · 2 ba · 1,122 sf | Eastbrook | $390,000 | $388,000 | −0.5% | 139 |
| 660 W Morse Boulevard Oct 2 · 3 bd · 3.5 ba · 3,286 sf | — | $2,800,000 | $2,695,000 | −3.8% | 108 |
| 311 E Morse Boulevard #4-5 Oct 2 · 2 bd · 2 ba · 1,763 sf | Phillips Circle | $975,000 | $925,000 | −5.1% | 20 |
| 446 Melrose Avenue Oct 2 · 4 bd · 2 ba · 2,640 sf | Virginia Heights | $1,525,000 | $1,495,000 | −2.0% | 167 |
| 1871 Bryan Avenue Oct 2 · 3 bd · 2 ba · 1,232 sf | lakeview terrace | $625,000 | $599,000 | −4.2% | 48 |
| 471 Holt Avenue Oct 2 · 4 bd · 3 ba · 2,528 sf | Winter Park Villas | $975,000 | $950,000 | −2.6% | 41 |
| 3006 Northwood Boulevard Oct 2 · 4 bd · 3 ba · 2,075 sf | Northwood Terrace | $950,000 | $925,000 | −2.6% | 110 |
| 2260 Coldstream Drive Oct 2 · 4 bd · 2 ba · 1,509 sf | Brookshire Heights | $699,000 | $675,000 | −3.4% | 30 |
| 1401 Aster Court Oct 2 · 4 bd · 2 ba · 1,653 sf | — | $414,900 | $399,999 | −3.6% | 79 |
| 3740 Hawthorne Lane Oct 2 · 3 bd · 2 ba · 1,645 sf | — | $435,000 | $430,000 | −1.1% | 74 |
| 1138 S Pennsylvania Avenue Oct 1 · 3 bd · 3 ba · 2,434 sf | Virginia Heights | $999,000 | $925,000 | −7.4% | 106 |
| 1927 Eland Avenue Oct 1 · 5 bd · 3 ba · 2,242 sf | Lake Bell Terrace | $820,000 | $799,000 | −2.6% | 234 |
| 811 Overspin Drive Oct 1 · 2 bd · 1 ba · 749 sf | Dubsdread Heights | $349,000 | $329,000 | −5.7% | 180 |
| 3302 Royal Street Oct 1 · 3 bd · 2 ba · 1,197 sf | Coronation | $274,900 | $269,900 | −1.8% | 33 |
| 1660 Gladiolas Drive Sep 30 · 3 bd · 2 ba · 2,047 sf | — | $509,900 | $495,000 | −2.9% | 54 |
| 330 Elkhorn Court Sep 29 · 3 bd · 2 ba · 1,570 sf | Winter Park Pines Merrie Oaks | $544,900 | $539,900 | −0.9% | 239 |
| 2758 Banchory Road Sep 28 · 3 bd · 2.5 ba · 1,539 sf | winter park pines | $639,000 | $619,500 | −3.1% | 373 |
Biggest cuts this week
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 125 S Interlachen Avenue #1 Oct 10 · 3 bd · 4 ba · 3,878 sf | — | $3,895,000 | $3,695,000 | −5.1% | 68 |
| 125 S Interlachen Avenue #2 Oct 11 · 3 bd · 4 ba · 3,244 sf | — | $3,150,000 | $2,995,000 | −4.9% | 71 |
| 702 Via Bella Oct 14 · 4 bd · 5.5 ba · 3,720 sf | Palmer Ave Lakeside Prop | $4,400,000 | $4,250,000 | −3.4% | 28 |
| 1404 Border Drive Oct 14 · 4 bd · 4 ba · 2,469 sf | Winter Park Village | $1,075,000 | $998,000 | −7.2% | 134 |
| 300 Carolina Avenue #402C Oct 11 · 3 bd · 2 ba · 1,350 sf | Park West Condo | $710,000 | $650,000 | −8.5% | 141 |
| 560 Ololu Drive Oct 15 · 2 bd · 2 ba · 1,086 sf | Killarney Circle | $899,000 | $849,000 | −5.6% | 311 |
| 1220 Howell Branch Road Oct 13 · 3 bd · 2 ba · 1,487 sf | — | $999,500 | $950,000 | −5.0% | 44 |
| 2430 Chantilly Avenue Oct 15 · 4 bd · 4 ba · 2,916 sf | Winter Park Village | $1,598,000 | $1,550,000 | −3.0% | 47 |
| 1517 Harmon Avenue Oct 13 · 4 bd · 3.5 ba · 2,135 sf | Lawndale | $1,095,000 | $1,049,000 | −4.2% | 24 |
| 1652 Berkshire Avenue Oct 8 · 3 bd · 2 ba · 1,498 sf | Orwin Manor Westminster | $479,000 | $449,000 | −6.3% | 59 |
Communities with the most reductions (30 days)
| Community | City | Reductions | Median cut |
|---|---|---|---|
| Orwin Manor Westminster | Winter Park | 4 | −3.1% |
| Kenilworth Shores | Winter Park | 3 | −1.6% |
| Eastbrook | Winter Park | 3 | −2.3% |
| Virginia Heights | Winter Park | 3 | −4.4% |
| Dubsdread Heights | Winter Park | 3 | −2.7% |
| Winter Park Villas | Winter Park | 3 | −2.6% |
| Winter Park Pines Merrie Oaks | Winter Park | 2 | −0.9% |
| Coronation | Winter Park | 2 | −1.8% |
| Winter Park Village | Winter Park | 2 | −5.1% |
| lakeview terrace | Winter Park | 2 | −3.9% |
| Winter Park Oasis | Winter Park | 2 | −3.2% |
| Lake Bell Terrace | Winter Park | 2 | −1.9% |
| Lazy Oaks Condo | Winter Park | 2 | −3.5% |
| Northwood Terrace | Winter Park | 2 | −2.6% |
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 October 15, 2026.