Homes under $500K in Winter Haven, FL
540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 14 of 36
- 5560 taverna loop, Winter Haven 33884 Pending $266,900 · 3 bd · 2 ba · 1,302 sqft
- 1355 benevento drive, Winter Haven 33884 Pending $319,900 · 4 bd · 3 ba · 1,964 sqft
- 3932 giorgio drive, Winter Haven 33884 Pending $274,190 · 3 bd · 2 ba · 1,695 sqft
- 3076 captain jax way, Winter Haven 33884 Pending $219,990 · 3 bd · 3 ba · 1,386 sqft
- 2018 marilyn avenue, Winter Haven 33881 Pending $299,900 · 3 bd · 2 ba · 1,651 sqft
- 1199 sophia boulevard, Winter Haven 33881 Pending $279,900 · 3 bd · 2 ba · 1,690 sqft
- 238 avenue f southeast, Winter Haven 33880 Pending $204,900 · 3 bd · 2 ba · 1,187 sqft
- 921 avenue east northeast, Winter Haven 33881 Pending $195,000 · 3 bd · 2 ba · 1,080 sqft
- 516 alachua drive, Winter Haven 33884 Pending $369,000 · 3 bd · 2 ba · 1,699 sqft
- 4663 ostero street, Winter Haven 33884 Pending $277,900 · 4 bd · 2 ba · 1,665 sqft
- 3009 captain jax way, Winter Haven 33884 Pending $219,990 · 3 bd · 3 ba · 1,386 sqft
- 3013 captain jax way, Winter Haven 33884 Pending $219,990 · 3 bd · 3 ba · 1,386 sqft
- 4045 giorgio drive, Winter Haven 33884 Pending $299,900 · 4 bd · 2 ba · 1,665 sqft
- 4079 lake marianna drive, Winter Haven 33881 Pending $184,900 · 3 bd · 2 ba · 1,054 sqft
- 1674 linz court, Winter Haven 33884 Pending $242,000 · 2 bd · 2 ba · 1,350 sqft
- 5337 hogan lane, Winter Haven 33884 Pending $355,000 · 3 bd · 2 ba · 1,833 sqft
- 2519 sage valley way, Winter Haven 33884 Pending $318,900 · 4 bd · 2 ba · 1,828 sqft
- 122 quailwood drive, Winter Haven 33880 Pending $359,900 · 3 bd · 2 ba · 1,666 sqft
- 1103 cypress gardens boulevard 30, Winter Haven 33884 Pending $115,000 · 1 bd · 1 ba · 475 sqft
- 6264 botticella boulevard, Winter Haven 33884 Pending $296,490 · 5 bd · 3 ba · 2,326 sqft
- 2531 sage valley way, Winter Haven 33884 Pending $321,900 · 4 bd · 2 ba · 1,828 sqft
- 2825 attwater loop, Winter Haven 33884 Pending $199,999 · 2 bd · 2 ba · 1,385 sqft
- 5437 san pietro drive, Winter Haven 33884 Pending $364,499 · 5 bd · 3 ba · 2,470 sqft
- 105 allen avenue, Winter Haven 33880 Pending $279,900 · 3 bd · 2 ba · 1,528 sqft
- 6253 botticella boulevard, Winter Haven 33884 Pending $252,990 · 4 bd · 3 ba · 1,880 sqft
- 132 lake mariam way, Winter Haven 33884 Pending $285,000 · 4 bd · 2 ba · 2,207 sqft
- 314 avenue y northeast, Winter Haven 33881 Pending $36,950 · 2 bd · 1 ba · 570 sqft
- 6276 botticella boulevard, Winter Haven 33884 Pending $305,490 · 5 bd · 3 ba · 2,326 sqft
- 6280 botticella boulevard, Winter Haven 33884 Pending $289,990 · 5 bd · 3 ba · 2,112 sqft
- 3334 white indigo road, Winter Haven 33884 Pending $289,900 · 3 bd · 2 ba · 1,504 sqft
- 5576 taverna loop, Winter Haven 33884 Pending $283,990 · 3 bd · 2 ba · 1,504 sqft
- 2741 gladiola road, Winter Haven 33884 Pending $273,990 · 3 bd · 3 ba · 1,758 sqft
- 2390 29th street northwest, Winter Haven 33881 Pending $209,900 · 4 bd · 2 ba · 1,048 sqft
- 2723 gladiola road, Winter Haven 33884 Pending $263,990 · 3 bd · 3 ba · 1,673 sqft
- 220 hartridge hills drive, Winter Haven 33881 Pending $369,900 · 3 bd · 3 ba · 2,383 sqft
- 516 reggie road, Winter Haven 33884 Pending $315,000 · 4 bd · 3 ba · 2,109 sqft
- 1749 south hummingbird road, Winter Haven 33884 Pending $408,700 · 4 bd · 3 ba · 2,336 sqft
- 1920 eloise cove drive, Winter Haven 33884 Pending $363,500 · 4 bd · 3 ba · 2,888 sqft
- 5820 taverna loop, Winter Haven 33884 Pending $305,990 · 5 bd · 3 ba · 2,326 sqft
- 2747 gladiola road, Winter Haven 33884 Pending $263,990 · 3 bd · 3 ba · 1,673 sqft
- 3022 firebrush lane, Winter Haven 33884 Pending $254,900 · 3 bd · 3 ba · 1,673 sqft
- 126 bermuda court, Winter Haven 33880 Pending $300,000 · 4 bd · 2 ba · 2,052 sqft
- 1502 eagle pond drive 15, Winter Haven 33884 Pending $159,900 · 2 bd · 2 ba · 1,017 sqft
- 2810 winterset park, Winter Haven 33884 Pending $340,000 · 3 bd · 2 ba · 1,898 sqft
- 1593 lemon avenue, Winter Haven 33881 Pending $285,000 · 4 bd · 2 ba · 1,761 sqft
- 3940 giorgio drive, Winter Haven 33884 Pending $292,490 · 3 bd · 2 ba · 1,269 sqft
- 713 bayside boulevard, Winter Haven 33881 Pending $279,900 · 3 bd · 2 ba · 1,479 sqft
- 611 ituna circle, Winter Haven 33881 Pending $303,900 · 3 bd · 2 ba · 1,644 sqft
- 724 bayside boulevard, Winter Haven 33881 Pending $291,680 · 3 bd · 2 ba · 1,486 sqft
- 512 ituna circle, Winter Haven 33881 Pending $324,625 · 3 bd · 2 ba · 1,545 sqft