Homes under $500K in Winter Haven, FL
540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 4 of 36
- 408 coleman drive, Winter Haven 33884 $389,900 · 4 bd · 2 ba · 2,420 sqft
- 1425 engelberg street, Winter Haven 33881 $345,000 · 4 bd · 2 ba · 1,989 sqft
- 231 hayley street, Winter Haven 33884 $319,999 · 4 bd · 3 ba · 1,933 sqft
- 628 pavare court #1, Winter Haven 33884 $99,000 · 2 bd · 2 ba · 823 sqft
- 1213 8th street northwest, Winter Haven 33881 $189,000 · 2 bd · 2 ba · 972 sqft
- 207 avenue east southeast, Winter Haven 33880 $394,900 · 4 bd · 4 ba · 2,230 sqft
- 405 valley court, Winter Haven 33884 $465,000 · 4 bd · 2 ba · 2,463 sqft
- 2747 san marco way, Winter Haven 33884 $284,990 · 3 bd · 2 ba · 1,680 sqft
- 144 waterside circle, Winter Haven 33880 $299,000 · 3 bd · 2 ba · 1,847 sqft
- 2015 recker highway, Winter Haven 33880 $309,900 · 3 bd · 2 ba · 1,322 sqft
- 573 lucerne boulevard, Winter Haven 33881 $250,000 · 3 bd · 2 ba · 1,743 sqft
- 3349 costello circle, Winter Haven 33884 $237,490 · 3 bd · 2 ba · 1,516 sqft
- 1814 sandhill lane, Winter Haven 33884 $462,000 · 4 bd · 3 ba · 2,550 sqft
- 511 marcia loop, Winter Haven 33884 $259,900 · 4 bd · 3 ba · 2,159 sqft
- 137 lowell road, Winter Haven 33884 $271,000 · 3 bd · 2 ba · 1,435 sqft
- 831 orchid springs dr ##831, Winter Haven 33884 $112,000 · 2 bd · 2 ba · 851 sqft
- 2500 21st street northwest #58, Winter Haven 33881 $150,000 · 3 bd · 3 ba · 1,334 sqft
- 689 lake howard drive northwest #213, Winter Haven 33880 $145,000 · 2 bd · 2 ba · 1,072 sqft
- 4162 roberta drive, Winter Haven 33881 $414,999 · 5 bd · 4 ba · 2,905 sqft
- 107 sanderling drive, Winter Haven 33881 $385,000 · 4 bd · 2 ba · 2,567 sqft
- 345 24th street northwest #1, Winter Haven 33880 $110,000 · 2 bd · 2 ba · 942 sqft
- 1050 michelangelo lane, Winter Haven 33884 $335,000 · 3 bd · 2 ba · 1,659 sqft
- 817 reflections loop east, Winter Haven 33884 $350,000 · 4 bd · 2 ba · 2,257 sqft
- 224 crown court, Winter Haven 33880 $269,000 · 3 bd · 2 ba · 1,192 sqft
- 1678 linz court, Winter Haven 33884 $245,000 · 2 bd · 2 ba · 1,158 sqft
- 3941 warbler drive, Winter Haven 33880 $234,900 · 4 bd · 3 ba · 1,936 sqft
- 341 meredith boulevard, Winter Haven 33881 $289,990 · 4 bd · 2 ba · 1,624 sqft
- 1714 upland lane, Winter Haven 33884 $424,900 · 4 bd · 3 ba · 2,565 sqft
- 701 magnolia place, Winter Haven 33884 $239,900 · 3 bd · 2 ba · 1,180 sqft
- 117 rebecca drive northeast, Winter Haven 33881 $255,000 · 3 bd · 2 ba · 1,221 sqft
- 1508 majestic lane, Winter Haven 33880 $324,500 · 4 bd · 3 ba · 1,900 sqft
- 1436 axel circle, Winter Haven 33880 $340,000 · 5 bd · 3 ba · 3,022 sqft
- 819 andrew street, Winter Haven 33881 $399,990 · 4 bd · 3 ba · 2,061 sqft
- 1248 31st street northwest, Winter Haven 33881 $195,000 · 2 bd · 1 ba · 840 sqft
- 2206 san marcos circle southeast, Winter Haven 33880 $210,000 · 2 bd · 2 ba · 1,224 sqft
- 415 8th street northeast, Winter Haven 33881 $255,000 · 3 bd · 2 ba · 1,652 sqft
- 2105 9th street northeast, Winter Haven 33881 $239,000 · 3 bd · 1 ba · 1,042 sqft
- 3129 avenue west northwest, Winter Haven 33881 $212,000 · 3 bd · 1 ba · 1,500 sqft
- 4332 cherrywood street, Winter Haven 33880 $115,000 · 2 bd · 2 ba · 1,150 sqft
- 824 vienna drive, Winter Haven 33884 $259,000 · 3 bd · 2 ba · 1,402 sqft
- 823 andrew street, Winter Haven 33881 $365,190 · 4 bd · 3 ba · 2,061 sqft
- 205 thomas court, Winter Haven 33880 $440,000 · 3 bd · 3 ba · 2,352 sqft
- 3400 sunset drive west, Winter Haven 33881 $194,500 · 3 bd · 1 ba · 936 sqft
- 432 ituna circle, Winter Haven 33881 $335,560 · 3 bd · 2 ba · 2,005 sqft
- 133 nemo lane, Winter Haven 33881 $239,900 · 3 bd · 3 ba · 1,544 sqft
- 3151 laurel oak lane, Winter Haven 33884 $333,900 · 4 bd · 3 ba · 2,029 sqft
- 4491 rapallo avenue, Winter Haven 33884 $312,900 · 3 bd · 2 ba · 1,744 sqft
- 6450 hollyberry lane northeast, Winter Haven 33881 $151,000 · 2 bd · 2 ba · 1,144 sqft
- 136 madera drive, Winter Haven 33880 $170,380 · 3 bd · 2 ba · 1,448 sqft
- 437 broward terrace, Winter Haven 33884 $390,000 · 4 bd · 2 ba · 1,687 sqft