Homes under $300K in Winter Haven, FL
441 for sale · 807 homes listed · Updated September 25, 2026 · Page 2 of 17
- 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
- 1301 evalyn drive southeast, Winter Haven 33880 $298,000 · 3 bd · 2 ba · 1,817 sqft
- 100 el camino drive 111, Winter Haven 33884 $65,000 · 1 bd · 1 ba · 931 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
- 1700 6th street northwest b24, Winter Haven 33881 $105,000 · 2 bd · 2 ba · 960 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
- 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
- 3829 giorgio, Winter Haven 33884 $242,000 · 3 bd · 2 ba
- 400 el camino drive 210, Winter Haven 33884 $96,000 · 3 bd · 3 ba · 1,666 sqft
- 3180 country club circle, Winter Haven 33881 $260,000 · 3 bd · 2 ba · 1,732 sqft
- 133 nemo lane, Winter Haven 33881 $244,900 · 3 bd · 3 ba · 1,544 sqft
- 541 heather glen drive, Winter Haven 33884 $269,999 · 3 bd · 2 ba · 1,453 sqft
- 1733 sandalwood circle southwest, Winter Haven 33880 $260,000 · 3 bd · 2 ba · 1,075 sqft
- 878 killearn boulevard, Winter Haven 33880 $245,000 · 3 bd · 2 ba · 1,467 sqft
- 2436 edwin street northeast, Winter Haven 33881 $218,995 · 4 bd · 2 ba · 1,813 sqft
- 188 sweet circle drive, Winter Haven 33884 $95,500 · 2 bd · 2 ba · 1,176 sqft
- 128 11th wahneta street west, Winter Haven 33880 $214,500 · 3 bd · 1 ba · 1,008 sqft
- 4228 cedarwood street, Winter Haven 33880 $118,000 · 2 bd · 2 ba · 1,104 sqft
- 6081 southern oaks drive southeast, Winter Haven 33884 $169,500 · 2 bd · 2 ba · 1,080 sqft
- 2122 lake boulevard, Winter Haven 33881 $248,000 · 3 bd · 1 ba · 985 sqft
- 447 san jose drive, Winter Haven 33884 $224,900 · 2 bd · 2 ba · 1,600 sqft
- 6825 south lake henry drive northeast, Winter Haven 33881 $220,000 · 2 bd · 2 ba · 1,790 sqft
- 4056 rolling oaks drive, Winter Haven 33880 $119,000 · 2 bd · 2 ba · 1,104 sqft
- 1798 white elephant loop, Winter Haven 33884 $279,900 · 3 bd · 2 ba · 1,526 sqft
- 1701 36th street northwest, Winter Haven 33881 $257,999 · 4 bd · 2 ba · 1,815 sqft
- 3777 giorgio drive, Winter Haven 33884 $289,900 · 3 bd · 2 ba · 1,695 sqft
- 1581 oakview circle southeast, Winter Haven 33880 $210,000 · 2 bd · 2 ba · 1,220 sqft
- 2362 brassie court, Winter Haven 33884 $265,000 · 3 bd · 2 ba · 1,260 sqft
- 961 drexel avenue northeast, Winter Haven 33881 $279,900 · 3 bd · 2 ba · 1,856 sqft
- 265 lake thomas drive, Winter Haven 33880 $299,950 · 3 bd · 2 ba · 1,517 sqft
- 111 sunset drive east, Winter Haven 33881 $200,000 · 4 bd · 1 ba · 2,078 sqft
- 4239 cedarwood street, Winter Haven 33880 $125,000 · 2 bd · 2 ba · 1,368 sqft
- 125 edgewater drive, Winter Haven 33881 $210,000 · 4 bd · 3 ba · 1,703 sqft
- 8304 waterview way 8304, Winter Haven 33884 $154,900 · 2 bd · 2 ba · 930 sqft
- 9705 lake bess road 715, Winter Haven 33884 $119,000 · 2 bd · 2 ba · 792 sqft
- 3339 queens cove loop, Winter Haven 33880 $234,900 · 3 bd · 2 ba · 1,158 sqft
- 2500 21st street northwest 23, Winter Haven 33881 $169,000 · 2 bd · 3 ba · 1,334 sqft
- 111 krenson bay loop, Winter Haven 33881 $280,000 · 3 bd · 2 ba · 1,543 sqft
- 330 sterling drive, Winter Haven 33884 $295,000 · 3 bd · 2 ba · 1,426 sqft
- 1533 majestic lane, Winter Haven 33880 $235,000 · 4 bd · 3 ba · 1,957 sqft
- 1799 carnostie road, Winter Haven 33884 $295,000 · 4 bd · 2 ba · 1,680 sqft
- 3316 white indigo road, Winter Haven 33884 $292,900 · 3 bd · 2 ba · 1,504 sqft
- 3935 palazzo place, Winter Haven 33884 $265,000 · 5 bd · 3 ba · 2,601 sqft