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