Homes under $500K in Winter Haven, FL
718 for sale · 1,258 homes listed · Updated September 27, 2026 · Page 3 of 26
- 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
- 1280 denali drive, Winter Haven 33881 $395,000 · 4 bd · 3 ba · 2,566 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
- 5764 royal hills circle, Winter Haven 33881 $329,000 · 4 bd · 3 ba · 2,278 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
- 194 south lake mariam drive, Winter Haven 33884 $390,000 · 2 bd · 2 ba · 1,538 sqft
- 183 lake thomas, Winter Haven 33880 $450,000 · 4 bd · 2 ba · 2,385 sqft
- 3777 giorgio drive, Winter Haven 33884 $289,900 · 3 bd · 2 ba · 1,695 sqft
- 5264 green drive, Winter Haven 33884 $315,000 · 3 bd · 2 ba · 2,011 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
- 3308 country walk club circle, Winter Haven 33881 $314,990 · 4 bd · 2 ba · 1,851 sqft
- 132 alachua drive, Winter Haven 33884 $310,000 · 3 bd · 2 ba · 2,466 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
- 802 marcia loop, Winter Haven 33884 $349,900 · 3 bd · 2 ba · 1,539 sqft
- 1015 corso drive, Winter Haven 33884 $367,000 · 5 bd · 4 ba · 3,200 sqft
- 3142 whispering trails street, Winter Haven 33884 $370,000 · 4 bd · 3 ba · 2,203 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
- 2118 edgewater circle, Winter Haven 33880 $369,000 · 4 bd · 3 ba · 2,763 sqft
- 9705 lake bess road 715, Winter Haven 33884 $119,000 · 2 bd · 2 ba · 792 sqft
- 605 sarner pass way, Winter Haven 33881 $399,000 · 4 bd · 3 ba · 2,676 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
- 953 cambridge drive, Winter Haven 33881 $395,000 · 4 bd · 3 ba · 2,364 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
- 111 las flores, Winter Haven 33884 $275,000 · 3 bd · 2 ba · 1,639 sqft