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.
74 homes for sale in Winter Haven, FL cut their asking price in the last 7 days and 214 in the last 30, out of 775 active listings (22% reduced at least once this month). The median reduction is 2.4% ($7,250). The largest cut this week was $100,000 on 4401 Chambliss Road in Winter Haven ($1,200,000 → $1,100,000).
Latest price reductions in Winter Haven
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 108 Lagoon Road Oct 13 · 3 bd · 2 ba · 1,735 sf | — | $340,000 | $299,900 | −11.8% | 73 |
| 604 Sarner Pass Way Oct 13 · 4 bd · 2 ba · 2,004 sf | — | $338,000 | $318,000 | −5.9% | 31 |
| 900 Lake Martha Drive Oct 13 · 4 bd · 4 ba · 3,408 sf | — | $460,000 | $440,000 | −4.3% | 21 |
| 258 Terranova Boulevard Oct 13 · 4 bd · 3 ba · 2,639 sf | — | $409,000 | $389,000 | −4.9% | 149 |
| 410 Laurel Cove Way Oct 13 · 2 bd · 2 ba · 1,090 sf | — | $215,000 | $209,000 | −2.8% | 62 |
| 1382 Salisbury Drive Oct 13 · 4 bd · 2.5 ba · 1,764 sf | — | $293,899 | $290,000 | −1.3% | 192 |
| 107 Lake Elizabeth Drive #B Oct 13 · 1 bd · 1 ba · 625 sf | — | $119,000 | $117,000 | −1.7% | 75 |
| 4401 Chambliss Road Oct 12 · 3 bd · 2 ba · 2,129 sf | — | $1,200,000 | $1,100,000 | −8.3% | 28 |
| 12 Saint Kitts Circle Oct 12 · 3 bd · 2 ba · 1,639 sf | — | $299,000 | $294,000 | −1.7% | 18 |
| 220 King Road Oct 12 · 2 bd · 1 ba · 672 sf | — | $119,000 | $114,900 | −3.4% | 197 |
| 1903 3Rd Street Oct 11 · 3 bd · 1 ba · 988 sf | — | $160,000 | $135,000 | −15.6% | 72 |
| 6825 S Lake Henry Drive Oct 11 · 2 bd · 2 ba · 1,790 sf | — | $220,000 | $200,000 | −9.1% | 241 |
| 3695 Julius Estates Boulevard Oct 11 · 4 bd · 2 ba · 1,842 sf | — | $310,000 | $305,000 | −1.6% | 53 |
| 2801 Wingfoot Court Oct 11 · 2 bd · 2 ba · 1,666 sf | — | $249,900 | $245,000 | −2.0% | 29 |
| 4913 Jackson Street Oct 10 · 3 bd · 2 ba · 1,425 sf | Jackson Landing | $232,000 | $206,400 | −11.0% | 154 |
| 217 4Th Jpv Street Oct 10 · 3 bd · 1 ba · 1,064 sf | — | $229,900 | $214,000 | −6.9% | 127 |
| 2207 Avenue F Oct 10 · 3 bd · 2 ba · 1,310 sf | — | $236,900 | $224,900 | −5.1% | 134 |
| 408 Coleman Drive Oct 10 · 4 bd · 2 ba · 2,420 sf | — | $389,900 | $379,900 | −2.6% | 57 |
| 1024 31St Street Oct 10 · 4 bd · 2 ba · 1,532 sf | — | $255,000 | $245,000 | −3.9% | 64 |
| 1705 Sandalwood Circle Oct 10 · 3 bd · 2 ba · 1,164 sf | — | $289,900 | $279,900 | −3.4% | 77 |
| 603 Maggie Circle Oct 10 · 3 bd · 2 ba · 1,482 sf | — | $255,000 | $245,000 | −3.9% | 139 |
| 1404 Axel Circle Oct 10 · 5 bd · 3 ba · 2,523 sf | — | $359,000 | $354,900 | −1.1% | 91 |
| 815 Andrew Street Oct 9 · 4 bd · 2 ba · 1,814 sf | — | $344,990 | $319,990 | −7.2% | 27 |
| 823 Andrew Street Oct 9 · 4 bd · 3 ba · 2,061 sf | — | $365,190 | $345,190 | −5.5% | 14 |
| 450 Sandestin Drive Oct 9 · 2 bd · 2 ba · 1,204 sf | — | $205,000 | $185,000 | −9.8% | 24 |
| 819 Andrew Street Oct 9 · 4 bd · 3 ba · 2,061 sf | — | $399,990 | $379,990 | −5.0% | 67 |
| 4162 Roberta Drive Oct 9 · 5 bd · 3.5 ba · 2,905 sf | — | $414,999 | $399,999 | −3.6% | 47 |
| 300 Greenfield Road Oct 9 · 4 bd · 2.5 ba · 2,350 sf | — | $425,000 | $410,000 | −3.5% | 54 |
| 503 Avenue B #503 Oct 9 · 2 bd · 2.5 ba · 1,408 sf | — | $314,999 | $299,999 | −4.8% | 67 |
| 302 Avenue P NW Oct 9 · 6 bd · 4 ba · 2,820 sf | — | $510,000 | $499,999 | −2.0% | 58 |
| 405 Valley Court Oct 9 · 4 bd · 2 ba · 2,463 sf | — | $465,000 | $455,000 | −2.2% | 40 |
| 1042 Corso Dr Oct 9 · 4 bd · 2 ba · 1,730 sf | — | $275,000 | $265,000 | −3.6% | 41 |
| 662 Eagle Landing Boulevard Oct 9 · 4 bd · 2.5 ba · 2,300 sf | — | $345,000 | $335,000 | −2.9% | 51 |
| 5268 Pebble Beach Boulevard Oct 9 · 3 bd · 2 ba · 2,354 sf | — | $579,900 | $569,900 | −1.7% | 183 |
| 2270 Firestone Place Oct 9 · 2 bd · 2 ba · 1,439 sf | — | $180,000 | $170,000 | −5.6% | 317 |
| 1321 Oakmont Drive Oct 9 · 3 bd · 2 ba · 2,312 sf | — | $434,700 | $424,900 | −2.3% | 7 |
| 605 Sarner Pass Way Oct 9 · 4 bd · 2.5 ba · 2,676 sf | — | $399,000 | $389,900 | −2.3% | 214 |
| 318 Hamilton Shores Drive Oct 9 · 4 bd · 2 ba · 2,806 sf | — | $533,000 | $524,000 | −1.7% | 42 |
| 3933 Giorgio Drive Oct 9 · 3 bd · 2 ba · 1,695 sf | — | $286,000 | $279,000 | −2.4% | 16 |
| 3541 Raleigh Drive Oct 9 · 3 bd · 3 ba · 2,006 sf | — | $350,000 | $345,000 | −1.4% | 21 |
| 3329 Fox Ridge Drive Oct 9 · 3 bd · 2 ba · 1,317 sf | — | $259,900 | $254,900 | −1.9% | 50 |
| 308 Vaniman Avenue Oct 9 · 3 bd · 2 ba · 1,228 sf | — | $229,900 | $224,900 | −2.2% | 93 |
| 3960 Giorgio Drive Oct 9 · 4 bd · 2 ba · 1,607 sf | — | $279,000 | $274,000 | −1.8% | 114 |
| 204 Kingshill Court Oct 9 · 3 bd · 2 ba · 1,437 sf | — | $254,900 | $249,900 | −2.0% | 175 |
| 232 Kings Pond Avenue Oct 9 · 3 bd · 2 ba · 1,417 sf | — | $294,989 | $289,999 | −1.7% | 66 |
| 4075 Bedford Avenue Oct 9 · 2 bd · 2 ba · 1,888 sf | — | $349,001 | $344,900 | −1.2% | 16 |
| 400 Bayou Road Oct 9 · 2 bd · 2 ba · 1,277 sf | — | $258,000 | $254,000 | −1.6% | 14 |
| 434 Avenue D Oct 9 · 2 bd · 1 ba · 900 sf | — | $209,000 | $205,000 | −1.9% | 73 |
| 754 Santa Maria Dr Oct 9 · 4 bd · 3 ba · 2,200 sf | — | $370,000 | $367,000 | −0.8% | 29 |
| 350 Winter Ridge Boulevard #350 Oct 9 · 2 bd · 2 ba · 1,073 sf | — | $148,000 | $145,000 | −2.0% | 32 |
| 2021 Oliver Place Oct 9 · 3 bd · 2 ba · 1,507 sf | — | $274,989 | $274,988 | −0.0% | 79 |
| 9469 Waterford Oaks Drive Oct 7 · 4 bd · 3 ba · 3,648 sf | — | $789,900 | $759,900 | −3.8% | 47 |
| 625 Avenue B Oct 7 · 2 bd · 2 ba · 1,240 sf | — | $250,000 | $230,000 | −8.0% | 34 |
| 961 Drexel Avenue Oct 7 · 3 bd · 2 ba · 1,856 sf | — | $279,900 | $260,000 | −7.1% | 219 |
| 707 Dolly Ben Court Oct 7 · 3 bd · 1 ba · 1,048 sf | — | $239,000 | $225,000 | −5.9% | 25 |
| 208 Golf Aire Boulevard Oct 7 · 3 bd · 2 ba · 2,145 sf | — | $249,950 | $239,000 | −4.4% | 3 |
| 3039 Captain Jax Way Oct 7 · 3 bd · 2.5 ba · 1,423 sf | — | $236,990 | $226,990 | −4.2% | 6 |
| 3059 Captain Jax Way Oct 7 · 3 bd · 2.5 ba · 1,423 sf | — | $236,990 | $226,990 | −4.2% | 6 |
| 3005 Captain Jax Way Oct 7 · 3 bd · 2.5 ba · 1,423 sf | — | $236,990 | $226,990 | −4.2% | 11 |
| 3021 Captain Jax Way Oct 7 · 3 bd · 2.5 ba · 1,386 sf | — | $224,990 | $214,990 | −4.4% | 12 |
Biggest cuts this week
| Listing | Community | Was | Now | Cut | DOM |
|---|---|---|---|---|---|
| 4401 Chambliss Road Oct 12 · 3 bd · 2 ba · 2,129 sf | — | $1,200,000 | $1,100,000 | −8.3% | 28 |
| 108 Lagoon Road Oct 13 · 3 bd · 2 ba · 1,735 sf | — | $340,000 | $299,900 | −11.8% | 73 |
| 9469 Waterford Oaks Drive Oct 7 · 4 bd · 3 ba · 3,648 sf | — | $789,900 | $759,900 | −3.8% | 47 |
| 4913 Jackson Street Oct 10 · 3 bd · 2 ba · 1,425 sf | Jackson Landing | $232,000 | $206,400 | −11.0% | 154 |
| 815 Andrew Street Oct 9 · 4 bd · 2 ba · 1,814 sf | — | $344,990 | $319,990 | −7.2% | 27 |
| 1903 3Rd Street Oct 11 · 3 bd · 1 ba · 988 sf | — | $160,000 | $135,000 | −15.6% | 72 |
| 823 Andrew Street Oct 9 · 4 bd · 3 ba · 2,061 sf | — | $365,190 | $345,190 | −5.5% | 14 |
| 450 Sandestin Drive Oct 9 · 2 bd · 2 ba · 1,204 sf | — | $205,000 | $185,000 | −9.8% | 24 |
| 625 Avenue B Oct 7 · 2 bd · 2 ba · 1,240 sf | — | $250,000 | $230,000 | −8.0% | 34 |
| 819 Andrew Street Oct 9 · 4 bd · 3 ba · 2,061 sf | — | $399,990 | $379,990 | −5.0% | 67 |
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 13, 2026.