Winter Haven, FL Price Reductions
A price reduction is the clearest signal a seller sends: the first number did not work. This tracker lists every Winter Haven 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.
76 homes for sale in Winter Haven, FL cut their asking price in the last 7 days and 277 in the last 30, out of 784 active listings (28% reduced at least once this month). The median reduction is 2.3% ($5,900). The largest cut this week was $59,000 on 2935 Plantation Road in Cypresswood Plantation ($588,900 → $529,900).
Latest price reductions in Winter Haven
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 668 Reggie Road Nov 3 · 3 bd · 2 ba · 1,432 sf | — | $285,000 | $265,000 | −7.0% | 18 |
| 280 Santa Rosa Drive Nov 3 · 3 bd · 2 ba · 2,251 sf | — | $415,000 | $399,500 | −3.7% | 71 |
| 124 Center Street Nov 3 · 3 bd · 2 ba · 1,306 sf | — | $165,000 | $155,000 | −6.1% | 101 |
| 395 San Jose Dr Nov 3 · 2 bd · 2 ba · 1,093 sf | Orchid Springs Patio Homes | $170,000 | $161,500 | −5.0% | 18 |
| 255 Haines Boulevard Nov 3 · 4 bd · 2 ba · 1,793 sf | — | $280,000 | $275,000 | −1.8% | 40 |
| 1015 Carefree Cove Drive Nov 3 · 4 bd · 1.5 ba · 1,104 sf | — | $204,900 | $199,900 | −2.4% | 224 |
| 220 King Road Nov 3 · 2 bd · 1 ba · 672 sf | — | $114,900 | $110,000 | −4.3% | 218 |
| 1041 Brooks Way Nov 3 · 3 bd · 2 ba · 1,863 sf | — | $337,500 | $336,500 | −0.3% | 88 |
| 5764 Royal Hills Circle Nov 3 · 4 bd · 2.5 ba · 2,278 sf | — | $325,000 | $324,000 | −0.3% | 248 |
| 2436 Edwin Street Nov 3 · 4 bd · 2 ba · 1,813 sf | — | $218,994 | $218,744 | −0.1% | 243 |
| 508 Eagle Pond Drive #508 Nov 2 · 2 bd · 2 ba · 1,017 sf | — | $159,000 | $158,000 | −0.6% | 63 |
| 213 10Th Wahneta Street Nov 2 · 2 bd · 1 ba · 826 sf | — | $145,998 | $145,997 | −0.0% | 43 |
| 3319 Avenue U Nov 1 · 2 bd · 1 ba · 840 sf | — | $145,000 | $135,000 | −6.9% | 103 |
| 417 Avenue G Nov 1 · 3 bd · 2 ba · 1,020 sf | — | $380,000 | $375,000 | −1.3% | 17 |
| 900 Lake Martha Drive Oct 31 · 4 bd · 4 ba · 3,408 sf | — | $440,000 | $420,000 | −4.5% | 42 |
| 1871 Emily Drive Oct 31 · 4 bd · 2 ba · 2,012 sf | — | $304,900 | $285,500 | −6.4% | 174 |
| 915 Hart Lake Court Oct 31 · 4 bd · 3 ba · 2,659 sf | — | $535,000 | $520,000 | −2.8% | 14 |
| 1321 Oakmont Drive Oct 31 · 3 bd · 2 ba · 2,312 sf | — | $419,000 | $409,000 | −2.4% | 32 |
| 5281 Pebble Beach Boulevard Oct 31 · 3 bd · 2 ba · 1,495 sf | — | $279,900 | $269,900 | −3.6% | 35 |
| 4750 Osprey Way Oct 31 · 4 bd · 2 ba · 1,986 sf | — | $305,000 | $295,000 | −3.3% | 39 |
| 507 Short Lane Oct 31 · 4 bd · 2 ba · 1,867 sf | — | $339,000 | $329,000 | −2.9% | 53 |
| 233 Kings Pond Avenue Oct 31 · 3 bd · 2 ba · 1,220 sf | — | $264,950 | $254,950 | −3.8% | 69 |
| 2748 San Marco Way Oct 31 · 3 bd · 2 ba · 1,734 sf | — | $312,750 | $305,750 | −2.2% | 144 |
| 702 Avenue C Oct 31 · 5 bd · 3 ba · 1,726 sf | — | $278,000 | $272,000 | −2.2% | 25 |
| 119 Lantern Lane Oct 31 · 2 bd · 2 ba · 1,134 sf | — | $215,000 | $210,000 | −2.3% | 63 |
| 4146 Sprucewood Street Oct 31 · 2 bd · 2 ba · 1,344 sf | — | $140,000 | $135,000 | −3.6% | 135 |
| 142 Morning Glory Circle Oct 31 · 3 bd · 2 ba · 1,887 sf | — | $284,500 | $280,000 | −1.6% | 163 |
| 6066 SE Southern Oaks Drive Oct 31 · 2 bd · 2 ba · 828 sf | — | $129,900 | $126,900 | −2.3% | 16 |
| 5604 Royal Hills Drive Oct 31 · 5 bd · 4 ba · 3,756 sf | — | $346,000 | $343,000 | −0.9% | 73 |
| 317 Avenue G Oct 31 · 4 bd · 3 ba · 1,610 sf | — | $240,000 | $239,900 | −0.0% | 144 |
| 2935 Plantation Road Oct 29 · 4 bd · 3.5 ba · 2,724 sf | Cypresswood Plantation | $588,900 | $529,900 | −10.0% | 222 |
| 202 Saint Lucie Road Oct 29 · 3 bd · 2 ba · 1,764 sf | — | $299,900 | $265,000 | −11.6% | 193 |
| 3132 Country Club Circle Oct 29 · 4 bd · 2 ba · 1,851 sf | — | $285,000 | $260,000 | −8.8% | 11 |
| 9513 Waterford Oaks Boulevard Oct 29 · 5 bd · 3.5 ba · 3,611 sf | — | $750,000 | $725,000 | −3.3% | 45 |
| 5809 Windridge Drive Oct 29 · 4 bd · 2.5 ba · 2,836 sf | — | $369,900 | $349,000 | −5.7% | 30 |
| 146 8Th Street Oct 29 · 3 bd · 2 ba · 1,404 sf | — | $250,000 | $229,999 | −8.0% | 61 |
| 117 Rebecca Drive Oct 29 · 3 bd · 2 ba · 1,221 sf | — | $255,000 | $239,900 | −5.9% | 41 |
| 2510 Cypress Gardens Boulevard Oct 29 · 5 bd · 3 ba · 3,482 sf | — | $865,000 | $849,900 | −1.7% | 63 |
| 1069 Sandpiper Loop Oct 29 · 4 bd · 3 ba · 2,034 sf | — | $379,999 | $364,900 | −4.0% | 62 |
| 909 Cambridge Drive Oct 29 · 3 bd · 2 ba · 1,506 sf | LUCERNE Park RESERVE | $251,900 | $236,900 | −6.0% | 199 |
| 1044 Luke Avenue Oct 29 · 4 bd · 2 ba · 1,758 sf | — | $309,990 | $294,990 | −4.8% | 26 |
| 1700 6Th Street #B24 Oct 29 · 2 bd · 2 ba · 960 sf | — | $95,000 | $80,000 | −15.8% | 297 |
| 318 Hamilton Shores Drive Oct 29 · 4 bd · 2 ba · 2,806 sf | — | $524,000 | $510,000 | −2.7% | 67 |
| 1015 Robin Lane Oct 29 · 3 bd · 2 ba · 1,632 sf | — | $359,900 | $349,000 | −3.0% | 111 |
| 124 Edgewater Drive Oct 29 · 3 bd · 1 ba · 1,244 sf | — | $239,999 | $229,900 | −4.2% | 35 |
| 503 William Avenue Oct 29 · 3 bd · 2 ba · 1,372 sf | — | $269,900 | $259,900 | −3.7% | 17 |
| 86 Lake Daisy Boulevard Oct 29 · 2 bd · 2 ba · 1,826 sf | — | $269,999 | $259,999 | −3.7% | 21 |
| 1631 Linz Court Oct 29 · 2 bd · 2 ba · 1,231 sf | — | $190,500 | $180,500 | −5.2% | 37 |
| 134 Lichtenwalter Road Oct 29 · 3 bd · 2 ba · 1,080 sf | — | $199,000 | $189,000 | −5.0% | 42 |
| 119 Sunfish Drive Oct 29 · 3 bd · 2.5 ba · 2,613 sf | — | $419,000 | $409,000 | −2.4% | 43 |
| 2363 Gerber Dairy Road Oct 29 · 3 bd · 2 ba · 1,620 sf | — | $220,000 | $210,000 | −4.5% | 47 |
| 1016 S Lake Mariam Drive Oct 29 · 5 bd · 3.5 ba · 3,694 sf | — | $750,000 | $740,000 | −1.3% | 64 |
| 344 Ruby Lake Loop Oct 29 · 4 bd · 2 ba · 2,215 sf | — | $409,000 | $399,000 | −2.4% | 69 |
| 5852 Marsh Landing Drive Oct 29 · 4 bd · 2 ba · 2,091 sf | — | $325,000 | $315,000 | −3.1% | 78 |
| 530 Sanctuary Boulevard Oct 29 · 4 bd · 3 ba · 3,619 sf | — | $629,900 | $619,900 | −1.6% | 244 |
| 754 Santa Maria Dr Oct 29 · 4 bd · 3 ba · 2,200 sf | — | $367,000 | $359,000 | −2.2% | 54 |
| 5814 Driftwood Drive Oct 29 · 3 bd · 2 ba · 1,246 sf | — | $295,000 | $289,000 | −2.0% | 32 |
| 1321 Oakmont Drive Oct 29 · 3 bd · 2 ba · 2,312 sf | — | $424,900 | $419,000 | −1.4% | 32 |
| 333 Lake Howard Drive #204D Oct 29 · 3 bd · 2 ba · 1,226 sf | — | $145,000 | $139,999 | −3.4% | 58 |
| 1056 Luke Avenue Oct 29 · 4 bd · 2 ba · 1,938 sf | — | $309,990 | $304,990 | −1.6% | 26 |
Biggest cuts this week
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 2935 Plantation Road Oct 29 · 4 bd · 3.5 ba · 2,724 sf | Cypresswood Plantation | $588,900 | $529,900 | −10.0% | 222 |
| 202 Saint Lucie Road Oct 29 · 3 bd · 2 ba · 1,764 sf | — | $299,900 | $265,000 | −11.6% | 193 |
| 3132 Country Club Circle Oct 29 · 4 bd · 2 ba · 1,851 sf | — | $285,000 | $260,000 | −8.8% | 11 |
| 9513 Waterford Oaks Boulevard Oct 29 · 5 bd · 3.5 ba · 3,611 sf | — | $750,000 | $725,000 | −3.3% | 45 |
| 5809 Windridge Drive Oct 29 · 4 bd · 2.5 ba · 2,836 sf | — | $369,900 | $349,000 | −5.7% | 30 |
| 146 8Th Street Oct 29 · 3 bd · 2 ba · 1,404 sf | — | $250,000 | $229,999 | −8.0% | 61 |
| 668 Reggie Road Nov 3 · 3 bd · 2 ba · 1,432 sf | — | $285,000 | $265,000 | −7.0% | 18 |
| 900 Lake Martha Drive Oct 31 · 4 bd · 4 ba · 3,408 sf | — | $440,000 | $420,000 | −4.5% | 42 |
| 1871 Emily Drive Oct 31 · 4 bd · 2 ba · 2,012 sf | — | $304,900 | $285,500 | −6.4% | 174 |
| 280 Santa Rosa Drive Nov 3 · 3 bd · 2 ba · 2,251 sf | — | $415,000 | $399,500 | −3.7% | 71 |
Communities with the most reductions (30 days)
| Community | City | Reductions | Median cut |
|---|---|---|---|
| LUCERNE Park RESERVE | Winter Haven | 2 | −4.0% |
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 3, 2026.