Homes under $500K in Winter Haven, FL

540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 30 of 36

41 greenfield court, Winter Haven 33884 Off market since Sep 2026 $355,000 · 3 bd · 2 ba · 2,054 sqft
3856 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $259,000 · 3 bd · 2 ba · 1,288 sqft
709 sarner pass way, Winter Haven 33881 Off market since Sep 2026 $279,900 · 4 bd · 3 ba · 3,016 sqft
706 avenue i northeast, Winter Haven 33881 Off market since Sep 2026 $295,000 · 3 bd · 2 ba · 1,925 sqft
1776 6th street northwest 807, Winter Haven 33881 Off market since Sep 2026 $162,000 · 2 bd · 2 ba · 1,347 sqft
1500 avenue g northeast, Winter Haven 33881 Off market since Sep 2026 $359,000 · 3 bd · 2 ba · 2,280 sqft
221 avenue c northeast, Winter Haven 33881 Off market since Sep 2026 $215,000 · 3 bd · 2 ba · 720 sqft
139 avenue g southeast, Winter Haven 33880 Off market since Sep 2026 $180,000 · 2 bd · 1 ba · 896 sqft
629 avenue a northeast, Winter Haven 33881 Off market since Sep 2026 $225,000 · 2 bd · 2 ba · 1,293 sqft
1700 6th street northwest a38, Winter Haven 33881 Off market since Sep 2026 $78,800 · 2 bd · 1 ba · 840 sqft
362 holly ridge road, Winter Haven 33880 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,355 sqft
315 lanceolate drive, Winter Haven 33880 Off market since Sep 2026 $469,000 · 3 bd · 2 ba · 2,153 sqft
5 moonlight lane, Winter Haven 33884 Off market since Sep 2026 $215,000 · 2 bd · 2 ba · 952 sqft
4 enclave drive, Winter Haven 33884 Off market since Sep 2026 $240,000 · 3 bd · 2 ba · 1,526 sqft
4919 st james drive, Winter Haven 33881 Off market since Sep 2026 $299,900 · 3 bd · 2 ba · 1,577 sqft
1015 robin lane, Winter Haven 33884 Off market since Sep 2026 $359,900 · 3 bd · 2 ba · 1,632 sqft
5203 waterview way 5203, Winter Haven 33884 Off market since Sep 2026 $159,900 · 2 bd · 2 ba · 930 sqft
1903 3rd street northeast, Winter Haven 33881 Off market since Sep 2026 $160,000 · 3 bd · 1 ba · 988 sqft
1831 carnostie road, Winter Haven 33884 Off market since Sep 2026 $278,000 · 4 bd · 2 ba · 1,680 sqft
3915 avenue q northwest, Winter Haven 33881 Off market since Sep 2026 $109,900 · 3 bd · 2 ba · 860 sqft
3831 pomelo drive, Winter Haven 33884 Sold on Aug 21, 2026 $350,490 · 5 bd · 3 ba · 2,077 sqft
200 el camino drive 306, Winter Haven 33884 Off market since Sep 2026 $94,900 · 1 bd · 1 ba · 1,078 sqft
2753 gladiola road, Winter Haven 33884 Off market since Sep 2026 $263,990 · 3 bd · 3 ba · 1,673 sqft
2759 gladiola road, Winter Haven 33884 Off market since Sep 2026 $263,990 · 3 bd · 3 ba · 1,673 sqft
2765 gladiola road, Winter Haven 33884 Off market since Sep 2026 $263,990 · 3 bd · 3 ba · 1,673 sqft
1514 hamlin street, Winter Haven 33881 Off market since Sep 2026 $349,900 · 3 bd · 2 ba · 2,035 sqft
3460 julius estates boulevard, Winter Haven 33881 Off market since Jul 2026 $170,000 · 3 bd · 2 ba · 2,013 sqft
2470 salzburg loop, Winter Haven 33884 Off market since Sep 2026 $280,000 · 3 bd · 2 ba · 1,935 sqft
3158 beauchamp court, Winter Haven 33884 Off market since Sep 2026 $488,500 · 4 bd · 3 ba · 2,552 sqft
2021 oliver place, Winter Haven 33881 Off market since Sep 2026 $274,990 · 3 bd · 2 ba · 1,507 sqft
392 kensington view drive, Winter Haven 33880 Off market since Sep 2026 $255,000 · 3 bd · 2 ba · 1,258 sqft
700 mirror terrace northwest 511, Winter Haven 33881 Off market since Sep 2026 $149,900 · 2 bd · 2 ba · 1,190 sqft
1700 6th street northwest c24, Winter Haven 33881 Off market since Sep 2026 $92,000 · 2 bd · 1 ba · 840 sqft
210 meadowbrook boulevard, Winter Haven 33881 Off market since Sep 2026 $380,000 · 5 bd · 3 ba · 2,696 sqft
297 meadowbrook boulevard, Winter Haven 33881 Off market since Sep 2026 $230,000 · 3 bd · 2 ba · 1,426 sqft
4132 martindale loop, Winter Haven 33884 Off market since Sep 2026 $399,900 · 4 bd · 3 ba · 1,894 sqft
2595 san marco way, Winter Haven 33884 Off market since Sep 2026 $320,000 · 4 bd · 2 ba · 2,004 sqft
6704 winterset gardens road, Winter Haven 33884 Off market since Sep 2026 $399,000 · 3 bd · 2 ba · 2,418 sqft
1714 upland lane, Winter Haven 33884 Off market since Sep 2026 $424,900 · 4 bd · 3 ba · 2,565 sqft
2435 5th street northeast, Winter Haven 33881 Off market since Aug 2026 $240,000 · 3 bd · 2 ba · 1,215 sqft
235 6th street northwest 307, Winter Haven 33881 Off market since Sep 2026 $125,000 · 1 bd · 1 ba · 714 sqft
650 9th street northeast, Winter Haven 33881 Off market since Sep 2026 $189,900 · 2 bd · 2 ba · 1,110 sqft
1973 carnostie road, Winter Haven 33884 Off market since Sep 2026 $237,500 · 4 bd · 2 ba · 1,828 sqft
2579 sage valley way, Winter Haven 33884 Off market since Sep 2026 $305,000 · 3 bd · 2 ba · 1,535 sqft
2508 avenue a southwest, Winter Haven 33880 Off market since Sep 2026 $205,000 · 3 bd · 1 ba · 850 sqft
906 avenue m southeast, Winter Haven 33880 Off market since Sep 2026 $349,900 · 3 bd · 2 ba · 1,890 sqft
1320 normandy heights circle, Winter Haven 33880 Off market since Sep 2026 $245,000 · 3 bd · 2 ba · 1,252 sqft
156 manseau drive, Winter Haven 33880 Off market since Sep 2026 $299,998 · 3 bd · 2 ba · 1,323 sqft
6022 grey heron drive, Winter Haven 33881 Off market since Sep 2026 $320,000 · 5 bd · 3 ba · 2,577 sqft
1705 sandalwood circle southwest, Winter Haven 33880 Off market since Sep 2026 $289,900 · 3 bd · 2 ba · 1,164 sqft