Homes under $500K in Winter Haven, FL
540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 22 of 36
- 1518 fuji court, Winter Haven 33881 Off market since Jul 2026 $285,900 · 3 bd · 2 ba · 1,537 sqft
- 400 el camino drive 210, Winter Haven 33884 Off market since Sep 2026 $96,000 · 3 bd · 3 ba · 1,666 sqft
- 2 casarena court, Winter Haven 33881 Off market since Jul 2026 $320,000 · 3 bd · 3 ba · 2,377 sqft
- 920 gotthard pass drive, Winter Haven 33881 Off market since Jul 2026 $394,999 · 4 bd · 3 ba · 2,654 sqft
- 1059 michelangelo lane, Winter Haven 33884 Off market since Jul 2026 $364,500 · 4 bd · 2 ba · 1,844 sqft
- 340 vail drive, Winter Haven 33884 Off market since Sep 2026 $365,000 · 4 bd · 3 ba · 2,042 sqft
- 123 ruby lake drive, Winter Haven 33884 Sold on Aug 26, 2026 $287,000 · 3 bd · 2 ba · 1,919 sqft
- 1280 denali drive, Winter Haven 33881 Off market since Sep 2026 $395,000 · 4 bd · 3 ba · 2,566 sqft
- 133 nemo lane, Winter Haven 33881 Off market since Sep 2026 $244,900 · 3 bd · 3 ba · 1,544 sqft
- 541 heather glen drive, Winter Haven 33884 Off market since Sep 2026 $269,999 · 3 bd · 2 ba · 1,453 sqft
- 1733 sandalwood circle southwest, Winter Haven 33880 Off market since Sep 2026 $260,000 · 3 bd · 2 ba · 1,075 sqft
- 878 killearn boulevard, Winter Haven 33880 Off market since Sep 2026 $245,000 · 3 bd · 2 ba · 1,467 sqft
- 2436 edwin street northeast, Winter Haven 33881 Off market since Sep 2026 $218,995 · 4 bd · 2 ba · 1,813 sqft
- 188 sweet circle drive, Winter Haven 33884 Off market since Sep 2026 $90,500 · 2 bd · 2 ba · 1,176 sqft
- 128 11th wahneta street west, Winter Haven 33880 Off market since Sep 2026 $214,500 · 3 bd · 1 ba · 1,008 sqft
- 6216 pinehurst loop, Winter Haven 33884 Off market since Aug 2026 $445,000 · 3 bd · 2 ba · 2,045 sqft
- 643 grove street, Winter Haven 33881 Off market since Sep 2026 $340,000 · 4 bd · 2 ba · 1,853 sqft
- 4228 cedarwood street, Winter Haven 33880 Off market since Sep 2026 $118,000 · 2 bd · 2 ba · 1,104 sqft
- 2285 avenue c southwest, Winter Haven 33880 Off market since Jul 2026 $275,900 · 4 bd · 2 ba · 2,325 sqft
- 5764 royal hills circle, Winter Haven 33881 Off market since Sep 2026 $329,000 · 4 bd · 3 ba · 2,278 sqft
- 6081 southern oaks drive southeast, Winter Haven 33884 Off market since Sep 2026 $169,500 · 2 bd · 2 ba · 1,080 sqft
- 2122 lake boulevard, Winter Haven 33881 Off market since Sep 2026 $248,000 · 3 bd · 1 ba · 985 sqft
- 4495 mandolin boulevard, Winter Haven 33884 Off market since Aug 2026 $335,000 · 4 bd · 2 ba · 1,903 sqft
- 1042 corso drive, Winter Haven 33884 Off market since Aug 2026 $289,900 · 4 bd · 2 ba · 1,730 sqft
- 6086 southern oaks drive southeast, Winter Haven 33884 Off market since Aug 2026 $180,000 · 2 bd · 2 ba · 1,040 sqft
- 447 san jose drive, Winter Haven 33884 Off market since Sep 2026 $224,900 · 2 bd · 2 ba · 1,600 sqft
- 6825 south lake henry drive northeast, Winter Haven 33881 Off market since Sep 2026 $220,000 · 2 bd · 2 ba · 1,790 sqft
- 4056 rolling oaks drive, Winter Haven 33880 Off market since Sep 2026 $114,900 · 2 bd · 2 ba · 1,104 sqft
- 1798 white elephant loop, Winter Haven 33884 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,526 sqft
- 1701 36th street northwest, Winter Haven 33881 Off market since Sep 2026 $257,999 · 4 bd · 2 ba · 1,815 sqft
- 3406 fox ridge street, Winter Haven 33884 Off market since Aug 2026 $275,000 · 3 bd · 2 ba · 1,392 sqft
- 1568 south lake shipp drive, Winter Haven 33880 Off market since Jul 2026 $254,700 · 3 bd · 2 ba · 1,032 sqft
- 208 lake howard drive northwest 104, Winter Haven 33880 Off market since Aug 2026 $174,900 · 2 bd · 2 ba · 1,152 sqft
- 194 south lake mariam drive, Winter Haven 33884 Off market since Sep 2026 $390,000 · 2 bd · 2 ba · 1,538 sqft
- 183 lake thomas, Winter Haven 33880 Off market since Sep 2026 $450,000 · 4 bd · 2 ba · 2,385 sqft
- 3777 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $289,900 · 3 bd · 2 ba · 1,695 sqft
- 3927 palazzo place, Winter Haven 33884 Off market since Jul 2026 $300,000 · 3 bd · 2 ba · 1,597 sqft
- 5264 green drive, Winter Haven 33884 Off market since Sep 2026 $315,000 · 3 bd · 2 ba · 2,011 sqft
- 1581 oakview circle southeast, Winter Haven 33880 Off market since Sep 2026 $210,000 · 2 bd · 2 ba · 1,220 sqft
- 2362 brassie court, Winter Haven 33884 Off market since Sep 2026 $265,000 · 3 bd · 2 ba · 1,260 sqft
- 1700 6th street northwest c31, Winter Haven 33881 Off market since Jul 2026 $99,900 · 2 bd · 2 ba · 840 sqft
- 1380 35th street northwest, Winter Haven 33881 Off market since Aug 2026 $129,900 · 2 bd · 1 ba · 720 sqft
- 961 drexel avenue northeast, Winter Haven 33881 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,856 sqft
- 3308 country walk club circle, Winter Haven 33881 Off market since Sep 2026 $314,990 · 4 bd · 2 ba · 1,851 sqft
- 132 alachua drive, Winter Haven 33884 Off market since Sep 2026 $310,000 · 3 bd · 2 ba · 2,466 sqft
- 265 lake thomas drive, Winter Haven 33880 Off market since Sep 2026 $299,950 · 3 bd · 2 ba · 1,517 sqft
- 111 sunset drive east, Winter Haven 33881 Off market since Sep 2026 $190,000 · 4 bd · 1 ba · 2,078 sqft
- 802 marcia loop, Winter Haven 33884 Off market since Sep 2026 $349,900 · 3 bd · 2 ba · 1,539 sqft
- 1015 corso drive, Winter Haven 33884 Off market since Sep 2026 $367,000 · 5 bd · 4 ba · 3,200 sqft
- 1023 corso drive, Winter Haven 33884 Off market since Jul 2026 $329,000 · 4 bd · 3 ba · 2,041 sqft