Homes under $500K in Winter Haven, FL
718 for sale · 1,258 homes listed · Updated September 25, 2026 · Page 2 of 26
- 335 columbo street, Winter Haven 33880 $385,900 · 4 bd · 3 ba · 2,242 sqft
- 344 alexzander way, Winter Haven 33881 $385,000 · 5 bd · 3 ba · 2,696 sqft
- 2307 scarlet avenue, Winter Haven 33884 $260,000 · 3 bd · 2 ba · 1,343 sqft
- 1601 roselawn street southwest, Winter Haven 33880 $256,500 · 2 bd · 1 ba · 1,099 sqft
- 6033 grand oaks drive southeast, Winter Haven 33884 $129,900 · 2 bd · 2 ba · 1,120 sqft
- 5331 mickey avenue, Winter Haven 33884 $354,999 · 4 bd · 3 ba · 2,670 sqft
- 400 el camino drive 223, Winter Haven 33884 $59,900 · 1 bd · 1 ba · 850 sqft
- 239 golf aire boulevard, Winter Haven 33884 $349,999 · 3 bd · 3 ba · 2,263 sqft
- 200 black skimmer lane, Winter Haven 33880 $285,000 · 3 bd · 2 ba · 1,265 sqft
- 6315 grove pointe drive southeast, Winter Haven 33884 $158,000 · 2 bd · 2 ba · 1,248 sqft
- 2739 rutledge court, Winter Haven 33884 $214,000 · 3 bd · 2 ba · 1,419 sqft
- 3971 island lakes drive, Winter Haven 33881 $434,900 · 3 bd · 2 ba · 2,023 sqft
- 1864 emily drive, Winter Haven 33884 $287,500 · 4 bd · 2 ba · 1,836 sqft
- 2270 firestone place, Winter Haven 33884 $180,000 · 2 bd · 2 ba · 1,439 sqft
- 5351 mickey avenue, Winter Haven 33884 $309,999 · 3 bd · 2 ba · 1,700 sqft
- 205 tifton street, Winter Haven 33880 $399,999 · 5 bd · 4 ba · 3,040 sqft
- 511 marcia loop, Winter Haven 33884 $259,900 · 4 bd · 3 ba · 2,159 sqft
- 3349 costello circle, Winter Haven 33884 $237,490 · 3 bd · 2 ba · 1,516 sqft
- 108 lake region boulevard north, Winter Haven 33881 $410,000 · 4 bd · 3 ba · 2,495 sqft
- 109 rebecca drive northeast, Winter Haven 33881 $239,500 · 3 bd · 2 ba · 1,560 sqft
- 271 inman boulevard, Winter Haven 33881 $340,000 · 5 bd · 3 ba · 2,274 sqft
- 469 muirfield court, Winter Haven 33884 $299,999 · 2 bd · 2 ba · 1,293 sqft
- 4251 cedarwood street, Winter Haven 33880 $106,000 · 2 bd · 2 ba · 1,216 sqft
- 3022 hickory street northwest, Winter Haven 33881 $265,000 · 3 bd · 1 ba · 1,602 sqft
- 4165 rolling oaks drive, Winter Haven 33880 $84,900 · 2 bd · 2 ba · 1,152 sqft
- 440 kensington view drive, Winter Haven 33880 $269,000 · 3 bd · 2 ba · 1,688 sqft
- 5197 pebble beach boulevard, Winter Haven 33884 $335,000 · 2 bd · 2 ba · 1,677 sqft
- 2795 adeline avenue, Winter Haven 33881 $301,900 · 5 bd · 2 ba · 1,708 sqft
- 4160 giorgio drive, Winter Haven 33884 $288,900 · 4 bd · 2 ba · 1,665 sqft
- 831 orchid springs drive #831, Winter Haven 33884 $112,000 · 2 bd · 2 ba · 851 sqft
- 2925 dayton drive, Winter Haven 33884 $284,500 · 3 bd · 2 ba · 2,109 sqft
- 951 lunar lane, Winter Haven 33884 $304,016 · 3 bd · 2 ba · 1,447 sqft
- 1301 evalyn drive southeast, Winter Haven 33880 $298,000 · 3 bd · 2 ba · 1,817 sqft
- 4577 back nine drive, Winter Haven 33884 $334,800 · 3 bd · 2 ba · 1,918 sqft
- 100 el camino drive 111, Winter Haven 33884 $65,000 · 1 bd · 1 ba · 931 sqft
- 129 lake otis road southeast, Winter Haven 33884 $325,000 · 5 bd · 3 ba · 2,579 sqft
- 3723 imperial drive, Winter Haven 33880 $250,000 · 3 bd · 2 ba · 1,264 sqft
- 7041 fairview village circle, Winter Haven 33881 $57,900 · 2 bd · 1 ba · 248 sqft
- 1726 hummingbird road, Winter Haven 33884 $310,990 · 3 bd · 2 ba · 1,593 sqft
- 1700 6th street northwest b24, Winter Haven 33881 $105,000 · 2 bd · 2 ba · 960 sqft
- 106 jardin lane, Winter Haven 33884 $399,900 · 3 bd · 2 ba · 2,319 sqft
- 4599 reynosa drive southwest, Winter Haven 33880 $309,999 · 3 bd · 2 ba · 2,309 sqft
- 6308 pinehurst loop, Winter Haven 33884 $452,000 · 3 bd · 2 ba · 2,045 sqft
- 525 squires grove drive, Winter Haven 33880 $290,000 · 4 bd · 2 ba · 1,872 sqft
- 940 oleander drive southeast, Winter Haven 33880 $250,000 · 2 bd · 2 ba · 1,527 sqft
- 6827 south lake henry drive northeast, Winter Haven 33881 $195,000 · 4 bd · 2 ba · 1,450 sqft
- 4913 jackson street, Winter Haven 33884 $232,000 · 3 bd · 2 ba · 1,425 sqft
- 148 lake otis road, Winter Haven 33884 $425,000 · 4 bd · 3 ba · 2,663 sqft
- 257 meadowbrook boulevard, Winter Haven 33881 $279,975 · 3 bd · 2 ba · 1,725 sqft
- 532 winter terrace, Winter Haven 33881 $164,000 · 3 bd · 2 ba · 1,073 sqft