Homes under $500K in Winter Haven, FL

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

1406 meadow drive northeast, Winter Haven 33881 Off market since Sep 2026 $225,000 · 3 bd · 2 ba · 1,678 sqft
1220 33rd street northwest, Winter Haven 33881 Off market since Jul 2026 $139,987 · 3 bd · 1 ba · 1,141 sqft
307 sterling drive, Winter Haven 33884 Off market since Sep 2026 $260,000 · 3 bd · 2 ba · 1,444 sqft
215 kilmer lane, Winter Haven 33884 Off market since Sep 2026 $379,998 · 4 bd · 3 ba · 1,680 sqft
820 avenue z northwest, Winter Haven 33881 Off market since Sep 2026 $197,500 · 3 bd · 2 ba · 2,082 sqft
2207 avenue f northwest, Winter Haven 33880 Off market since Sep 2026 $236,900 · 3 bd · 2 ba · 1,310 sqft
3408 costello circle, Winter Haven 33884 Off market since Sep 2026 $315,000 · 4 bd · 2 ba · 1,713 sqft
4519 rapallo avenue, Winter Haven 33884 Off market since Sep 2026 $329,900 · 4 bd · 3 ba · 2,074 sqft
134 lake hazel drive, Winter Haven 33884 Off market since Sep 2026 $90,000 · 2 bd · 2 ba · 1,352 sqft
2026 kings crossing southwest, Winter Haven 33880 Off market since Aug 2026 $214,900 · 2 bd · 2 ba · 1,131 sqft
5312 nicklaus drive, Winter Haven 33884 Off market since Sep 2026 $334,900 · 3 bd · 2 ba · 1,700 sqft
704 eagle pond drive 704, Winter Haven 33884 Off market since Sep 2026 $169,900 · 2 bd · 2 ba · 1,017 sqft
700 mirror terrace northwest 507, Winter Haven 33881 Off market since Sep 2026 $164,900 · 2 bd · 2 ba · 1,351 sqft
3268 country walk club circle, Winter Haven 33881 Off market since Sep 2026 $295,000 · 3 bd · 2 ba · 1,690 sqft
2108 cartgate lane, Winter Haven 33884 Off market since Sep 2026 $309,000 · 3 bd · 2 ba · 1,961 sqft
419 greenfield road, Winter Haven 33884 Off market since Sep 2026 $334,990 · 3 bd · 2 ba · 1,924 sqft
1217 michelangelo lane, Winter Haven 33884 Off market since Sep 2026 $405,000 · 4 bd · 4 ba · 2,960 sqft
306 eagle pond drive, Winter Haven 33884 Off market since Sep 2026 $211,000 · 2 bd · 2 ba · 1,017 sqft
3097 buckeye pointe drive, Winter Haven 33881 Off market since Sep 2026 $430,000 · 5 bd · 3 ba · 2,577 sqft
132 duval road, Winter Haven 33884 Off market since Sep 2026 $299,500 · 2 bd · 2 ba · 1,260 sqft
1716 terry circle northeast, Winter Haven 33881 Off market since Sep 2026 $270,000 · 3 bd · 2 ba · 1,065 sqft
270 meadowbrook boulevard, Winter Haven 33881 Off market since Sep 2026 $355,900 · 5 bd · 3 ba · 2,696 sqft
5638 royal hills street, Winter Haven 33881 Off market since Aug 2026 $329,900 · 4 bd · 2 ba · 2,012 sqft
333 lake howard drive northwest 314d, Winter Haven 33880 Off market since Sep 2026 $99,000 · 3 bd · 2 ba · 1,226 sqft
3928 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $279,150 · 4 bd · 2 ba · 1,607 sqft
614 sidney circle, Winter Haven 33880 Off market since Sep 2026 $389,999 · 3 bd · 2 ba · 1,908 sqft
6 golfview circle northeast, Winter Haven 33881 Off market since Sep 2026 $299,900 · 3 bd · 3 ba · 1,892 sqft
996 summer glen drive, Winter Haven 33880 Off market since Sep 2026 $299,900 · 4 bd · 2 ba · 1,851 sqft
3038 thornhill road, Winter Haven 33880 Off market since Sep 2026 $359,950 · 3 bd · 2 ba · 1,467 sqft
1026 medinah drive, Winter Haven 33884 Off market since Sep 2026 $172,500 · 2 bd · 2 ba · 1,398 sqft
2049 san marcos drive southeast 127, Winter Haven 33880 Off market since Sep 2026 $149,900 · 1 bd · 1 ba · 666 sqft
217 4th jpv street, Winter Haven 33880 Off market since Sep 2026 $229,900 · 3 bd · 1 ba · 1,064 sqft
719 avenue q southeast, Winter Haven 33880 Off market since Sep 2026 $220,000 · 2 bd · 2 ba · 1,181 sqft
4132 sprucewood street, Winter Haven 33880 Off market since Sep 2026 $129,000 · 2 bd · 2 ba · 1,344 sqft
204 avenue d northeast, Winter Haven 33881 Off market since Sep 2026 $250,000 · 6 bd · 3 ba · 2,102 sqft
301 terranova boulevard, Winter Haven 33884 Off market since Sep 2026 $379,900 · 4 bd · 2 ba · 1,960 sqft
265 majestic gardens lane, Winter Haven 33880 Off market since Sep 2026 $299,999 · 3 bd · 2 ba · 1,951 sqft
151 1st street, Winter Haven 33880 Off market since Sep 2026 $258,000 · 3 bd · 2 ba · 1,259 sqft
563 honey bell road, Winter Haven 33880 Off market since Sep 2026 $299,900 · 4 bd · 2 ba · 1,851 sqft
4840 old lucerne park road, Winter Haven 33881 Off market since Sep 2026 $415,000 · 3 bd · 2 ba · 1,927 sqft
4158 rolling oaks drive, Winter Haven 33880 Off market since Sep 2026 $124,900 · 2 bd · 2 ba · 1,403 sqft
531 heather glen drive, Winter Haven 33884 Off market since Sep 2026 $265,000 · 3 bd · 2 ba · 1,535 sqft
146 lake ring drive, Winter Haven 33884 Off market since Sep 2026 $364,999 · 3 bd · 2 ba · 1,638 sqft
4129 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $284,900 · 3 bd · 2 ba · 1,504 sqft
3184 royal tern drive, Winter Haven 33881 Off market since Sep 2026 $286,900 · 3 bd · 2 ba · 1,725 sqft
124 center street, Winter Haven 33880 Off market since Sep 2026 $165,000 · 3 bd · 2 ba · 1,306 sqft
381 san jose drive, Winter Haven 33884 Off market since Sep 2026 $229,900 · 3 bd · 2 ba · 1,651 sqft
3357 timberline road west, Winter Haven 33880 Off market since Sep 2026 $265,000 · 4 bd · 2 ba · 1,675 sqft
2748 san marco way, Winter Haven 33884 Off market since Sep 2026 $322,750 · 3 bd · 2 ba · 1,734 sqft
3467 julius estates boulevard, Winter Haven 33881 Off market since Sep 2026 $269,000 · 3 bd · 2 ba · 1,750 sqft