Homes under $300K in Winter Haven, FL
333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 14 of 23
- 1601 roselawn street southwest, Winter Haven 33880 Off market since Sep 2026 $256,500 · 2 bd · 1 ba · 1,099 sqft
- 6033 grand oaks drive southeast, Winter Haven 33884 Off market since Sep 2026 $129,900 · 2 bd · 2 ba · 1,120 sqft
- 21 casarena court, Winter Haven 33881 Off market since Jul 2026 $285,000 · 2 bd · 3 ba · 2,045 sqft
- 400 el camino drive 223, Winter Haven 33884 Off market since Sep 2026 $59,900 · 1 bd · 1 ba · 850 sqft
- 200 black skimmer lane, Winter Haven 33880 Off market since Sep 2026 $285,000 · 3 bd · 2 ba · 1,265 sqft
- 6315 grove pointe drive southeast, Winter Haven 33884 Off market since Sep 2026 $158,000 · 2 bd · 2 ba · 1,248 sqft
- 5580 state road 542 west, Winter Haven 33880 Off market since Sep 2026 $235,000 · 4 bd · 3 ba · 2,174 sqft
- 2739 rutledge court, Winter Haven 33884 Off market since Sep 2026 $214,000 · 3 bd · 2 ba · 1,419 sqft
- 1864 emily drive, Winter Haven 33884 Off market since Sep 2026 $287,500 · 4 bd · 2 ba · 1,836 sqft
- 2270 firestone place, Winter Haven 33884 Off market since Sep 2026 $180,000 · 2 bd · 2 ba · 1,439 sqft
- 511 marcia loop, Winter Haven 33884 Off market since Sep 2026 $259,900 · 4 bd · 3 ba · 2,159 sqft
- 3349 costello circle, Winter Haven 33884 Off market since Sep 2026 $237,490 · 3 bd · 2 ba · 1,516 sqft
- 109 rebecca drive northeast, Winter Haven 33881 Off market since Sep 2026 $239,500 · 3 bd · 2 ba · 1,560 sqft
- 4251 cedarwood street, Winter Haven 33880 Off market since Sep 2026 $106,000 · 2 bd · 2 ba · 1,216 sqft
- 1085 brenton manor drive, Winter Haven 33881 Off market since Sep 2026 $288,500 · 3 bd · 2 ba · 1,770 sqft
- 3022 hickory street northwest, Winter Haven 33881 Off market since Sep 2026 $265,000 · 3 bd · 1 ba · 1,602 sqft
- 4165 rolling oaks drive, Winter Haven 33880 Off market since Sep 2026 $84,900 · 2 bd · 2 ba · 1,152 sqft
- 440 kensington view drive, Winter Haven 33880 Off market since Sep 2026 $269,000 · 3 bd · 2 ba · 1,688 sqft
- 4160 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $288,900 · 4 bd · 2 ba · 1,665 sqft
- 831 orchid springs drive #831, Winter Haven 33884 Off market since Sep 2026 $112,000 · 2 bd · 2 ba · 851 sqft
- 2925 dayton drive, Winter Haven 33884 Off market since Sep 2026 $284,500 · 3 bd · 2 ba · 2,109 sqft
- 1301 evalyn drive southeast, Winter Haven 33880 Off market since Sep 2026 $295,000 · 3 bd · 2 ba · 1,817 sqft
- 100 el camino drive 111, Winter Haven 33884 Off market since Sep 2026 $65,000 · 1 bd · 1 ba · 931 sqft
- 3723 imperial drive, Winter Haven 33880 Off market since Sep 2026 $250,000 · 3 bd · 2 ba · 1,264 sqft
- 7041 fairview village circle, Winter Haven 33881 Off market since Sep 2026 $57,900 · 2 bd · 1 ba · 248 sqft
- 1195 tyler loop, Winter Haven 33884 Off market since Aug 2026 $299,997 · 4 bd · 3 ba · 1,933 sqft
- 1700 6th street northwest b24, Winter Haven 33881 Off market since Sep 2026 $105,000 · 2 bd · 2 ba · 960 sqft
- 306 avenue a wahneta east, Winter Haven 33880 Off market since Jul 2026 $179,900 · 5 bd · 2 ba · 1,747 sqft
- 525 squires grove drive, Winter Haven 33880 Off market since Sep 2026 $290,000 · 4 bd · 2 ba · 1,872 sqft
- 940 oleander drive southeast, Winter Haven 33880 Off market since Sep 2026 $250,000 · 2 bd · 2 ba · 1,527 sqft
- 6827 south lake henry drive northeast, Winter Haven 33881 Off market since Sep 2026 $195,000 · 4 bd · 2 ba · 1,450 sqft
- 4913 jackson street, Winter Haven 33884 Off market since Sep 2026 $232,000 · 3 bd · 2 ba · 1,425 sqft
- 4420 limewood street, Winter Haven 33880 Off market since Jul 2026 $105,000 · 2 bd · 2 ba · 864 sqft
- 257 meadowbrook boulevard, Winter Haven 33881 Off market since Sep 2026 $279,975 · 3 bd · 2 ba · 1,725 sqft
- 1700 6th street northwest c1, Winter Haven 33881 Off market since Jul 2026 $109,900 · 2 bd · 2 ba · 840 sqft
- 532 winter terrace, Winter Haven 33881 Off market since Sep 2026 $164,000 · 3 bd · 2 ba · 1,073 sqft
- 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
- 123 ruby lake drive, Winter Haven 33884 Sold on Aug 26, 2026 $287,000 · 3 bd · 2 ba · 1,919 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
- 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
- 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