Homes under $500K in Winter Haven, FL

540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 33 of 36

345 24th street northwest 1, Winter Haven 33880 Off market since Sep 2026 $110,000 · 2 bd · 2 ba · 942 sqft
107 sanderling drive, Winter Haven 33881 Off market since Sep 2026 $385,000 · 4 bd · 2 ba · 2,567 sqft
6631 thornhill road, Winter Haven 33880 Off market since Sep 2026 $320,000 · 3 bd · 2 ba · 1,221 sqft
106 majestic gardens court, Winter Haven 33880 Off market since Sep 2026 $275,000 · 3 bd · 2 ba · 1,661 sqft
1248 31st street northwest, Winter Haven 33881 Off market since Sep 2026 $195,000 · 2 bd · 1 ba · 840 sqft
2608 trinity circle northwest, Winter Haven 33881 Off market since Sep 2026 $239,900 · 2 bd · 2 ba · 1,092 sqft
300 greenfield road, Winter Haven 33884 Off market since Sep 2026 $425,000 · 4 bd · 3 ba · 2,350 sqft
3462 avenue t northwest, Winter Haven 33881 Off market since Sep 2026 $220,000 · 3 bd · 1 ba · 1,339 sqft
1187 tyler loop, Winter Haven 33884 Off market since Sep 2026 $350,000 · 5 bd · 3 ba · 2,254 sqft
6229 knotty pine drive southeast, Winter Haven 33884 Off market since Sep 2026 $180,000 · 3 bd · 2 ba · 1,504 sqft
207 avenue east southeast, Winter Haven 33880 Off market since Sep 2026 $394,900 · 4 bd · 4 ba · 2,230 sqft
5852 marsh landing drive, Winter Haven 33881 Off market since Sep 2026 $322,900 · 4 bd · 2 ba · 2,091 sqft
2500 21st street northwest 58, Winter Haven 33881 Off market since Sep 2026 $150,000 · 3 bd · 3 ba · 1,334 sqft
242 winter ridge boulevard 242, Winter Haven 33881 Off market since Sep 2026 $135,000 · 2 bd · 2 ba · 1,073 sqft
280 santa rosa drive, Winter Haven 33884 Off market since Sep 2026 $430,000 · 3 bd · 2 ba · 2,251 sqft
214 king road, Winter Haven 33880 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,124 sqft
723 24th street northwest, Winter Haven 33881 Off market since Sep 2026 $279,900 · 3 bd · 3 ba · 1,364 sqft
506 clayton circle, Winter Haven 33880 Off market since Sep 2026 $309,900 · 4 bd · 3 ba · 2,004 sqft
3735 imperial drive, Winter Haven 33880 Off market since Sep 2026 $244,900 · 3 bd · 2 ba · 1,393 sqft
662 eagle landing boulevard, Winter Haven 33880 Off market since Sep 2026 $345,000 · 4 bd · 3 ba · 2,300 sqft
3695 julius estates boulevard, Winter Haven 33881 Off market since Sep 2026 $310,000 · 4 bd · 2 ba · 1,842 sqft
1425 engelberg street, Winter Haven 33881 Off market since Sep 2026 $345,000 · 4 bd · 2 ba · 1,989 sqft
3329 fox ridge drive, Winter Haven 33884 Off market since Sep 2026 $259,900 · 3 bd · 2 ba · 1,317 sqft
6703 canterbury drive northeast, Winter Haven 33881 Off market since Sep 2026 $158,500 · 2 bd · 2 ba · 1,404 sqft
701 magnolia place, Winter Haven 33884 Off market since Sep 2026 $239,900 · 3 bd · 2 ba · 1,180 sqft
153 browning circle, Winter Haven 33884 Off market since Sep 2026 $269,000 · 3 bd · 2 ba · 1,144 sqft
5888 windridge drive, Winter Haven 33881 Off market since Sep 2026 $330,000 · 4 bd · 3 ba · 2,836 sqft
576 ituna circle, Winter Haven 33881 Off market since Sep 2026 $320,480 · 3 bd · 2 ba · 1,545 sqft
432 ituna circle, Winter Haven 33881 Off market since Sep 2026 $335,560 · 3 bd · 2 ba · 2,005 sqft
540 ituna circle, Winter Haven 33881 Off market since Sep 2026 $353,290 · 4 bd · 3 ba · 2,029 sqft
187 sweet circle, Winter Haven 33884 Off market since Sep 2026 $75,000 · 2 bd · 2 ba · 864 sqft
5638 royal hills street, Winter Haven 33881 Off market since Sep 2026 $299,500 · 4 bd · 2 ba · 2,012 sqft
715 ave c southwest, Winter Haven 33880 Off market since Sep 2026 $379,900 · 3 bd · 1 ba · 1,538 sqft
1370 salisbury drive, Winter Haven 33881 Off market since Sep 2026 $295,000 · 4 bd · 3 ba · 1,874 sqft
86 parson drive, Winter Haven 33884 Off market since Sep 2026 $103,000 · 2 bd · 2 ba · 1,260 sqft
4162 roberta drive, Winter Haven 33881 Off market since Sep 2026 $414,999 · 5 bd · 4 ba · 2,905 sqft
795 crosstower drive, Winter Haven 33880 Off market since Sep 2026 $435,000 · 3 bd · 2 ba · 1,572 sqft
5604 royal hills drive, Winter Haven 33881 Off market since Sep 2026 $357,000 · 5 bd · 4 ba · 3,756 sqft
534 lake dexter boulevard, Winter Haven 33884 Off market since Sep 2026 $270,000 · 3 bd · 2 ba · 1,470 sqft
1776 6th street northwest 409, Winter Haven 33881 Off market since Sep 2026 $119,000 · 2 bd · 2 ba · 1,347 sqft
845 avenue f northeast, Winter Haven 33881 Off market since Sep 2026 $309,900 · 3 bd · 2 ba · 1,552 sqft
501 avenue g southeast, Winter Haven 33880 Off market since Sep 2026 $319,900 · 4 bd · 2 ba · 1,816 sqft
213 lakeside ranch circle, Winter Haven 33881 Off market since Sep 2026 $54,900 · 2 bd · 1 ba · 672 sqft
344 ruby lake loop, Winter Haven 33884 Off market since Sep 2026 $409,000 · 4 bd · 2 ba · 2,215 sqft
215 santa rosa drive, Winter Haven 33884 Off market since Sep 2026 $304,900 · 4 bd · 2 ba · 2,355 sqft
233 kings pond avenue, Winter Haven 33880 Off market since Sep 2026 $264,950 · 3 bd · 2 ba · 1,220 sqft
418 majestic gardens boulevard, Winter Haven 33880 Off market since Sep 2026 $324,900 · 4 bd · 2 ba · 1,824 sqft
708 avenue east northeast, Winter Haven 33881 Off market since Sep 2026 $174,500 · 2 bd · 1 ba · 918 sqft
218 5th jpv street, Winter Haven 33880 Off market since Sep 2026 $258,610 · 5 bd · 2 ba · 820 sqft
981 lunar lane, Winter Haven 33884 Off market since Sep 2026 $335,924 · 4 bd · 2 ba · 1,919 sqft