Homes under $300K in Winter Haven, FL
333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 15 of 23
- 1042 corso drive, Winter Haven 33884 Off market since Aug 2026 $289,900 · 4 bd · 2 ba · 1,730 sqft
- 6086 southern oaks drive southeast, Winter Haven 33884 Off market since Aug 2026 $180,000 · 2 bd · 2 ba · 1,040 sqft
- 447 san jose drive, Winter Haven 33884 Off market since Sep 2026 $224,900 · 2 bd · 2 ba · 1,600 sqft
- 6825 south lake henry drive northeast, Winter Haven 33881 Off market since Sep 2026 $220,000 · 2 bd · 2 ba · 1,790 sqft
- 4056 rolling oaks drive, Winter Haven 33880 Off market since Sep 2026 $114,900 · 2 bd · 2 ba · 1,104 sqft
- 1798 white elephant loop, Winter Haven 33884 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,526 sqft
- 1701 36th street northwest, Winter Haven 33881 Off market since Sep 2026 $257,999 · 4 bd · 2 ba · 1,815 sqft
- 3406 fox ridge street, Winter Haven 33884 Off market since Aug 2026 $275,000 · 3 bd · 2 ba · 1,392 sqft
- 1568 south lake shipp drive, Winter Haven 33880 Off market since Jul 2026 $254,700 · 3 bd · 2 ba · 1,032 sqft
- 208 lake howard drive northwest 104, Winter Haven 33880 Off market since Aug 2026 $174,900 · 2 bd · 2 ba · 1,152 sqft
- 3777 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $289,900 · 3 bd · 2 ba · 1,695 sqft
- 1581 oakview circle southeast, Winter Haven 33880 Off market since Sep 2026 $210,000 · 2 bd · 2 ba · 1,220 sqft
- 2362 brassie court, Winter Haven 33884 Off market since Sep 2026 $265,000 · 3 bd · 2 ba · 1,260 sqft
- 1700 6th street northwest c31, Winter Haven 33881 Off market since Jul 2026 $99,900 · 2 bd · 2 ba · 840 sqft
- 1380 35th street northwest, Winter Haven 33881 Off market since Aug 2026 $129,900 · 2 bd · 1 ba · 720 sqft
- 961 drexel avenue northeast, Winter Haven 33881 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,856 sqft
- 265 lake thomas drive, Winter Haven 33880 Off market since Sep 2026 $299,950 · 3 bd · 2 ba · 1,517 sqft
- 111 sunset drive east, Winter Haven 33881 Off market since Sep 2026 $190,000 · 4 bd · 1 ba · 2,078 sqft
- 4239 cedarwood street, Winter Haven 33880 Off market since Sep 2026 $125,000 · 2 bd · 2 ba · 1,368 sqft
- 125 edgewater drive, Winter Haven 33881 Off market since Sep 2026 $210,000 · 4 bd · 3 ba · 1,703 sqft
- 6433 jacaranda avenue northeast, Winter Haven 33881 Off market since Aug 2026 $145,000 · 2 bd · 2 ba · 912 sqft
- 8304 waterview way 8304, Winter Haven 33884 Off market since Sep 2026 $154,900 · 2 bd · 2 ba · 930 sqft
- 9705 lake bess road 715, Winter Haven 33884 Off market since Sep 2026 $119,000 · 2 bd · 2 ba · 792 sqft
- 3339 queens cove loop, Winter Haven 33880 Off market since Sep 2026 $234,900 · 3 bd · 2 ba · 1,158 sqft
- 2500 21st street northwest 23, Winter Haven 33881 Off market since Sep 2026 $169,000 · 2 bd · 3 ba · 1,334 sqft
- 111 krenson bay loop, Winter Haven 33881 Off market since Sep 2026 $280,000 · 3 bd · 2 ba · 1,543 sqft
- 1533 majestic lane, Winter Haven 33880 Off market since Sep 2026 $235,000 · 4 bd · 3 ba · 1,957 sqft
- 1910 40th street northwest, Winter Haven 33881 Off market since Sep 2026 $215,000 · 4 bd · 2 ba · 1,584 sqft
- 221 golf aire boulevard, Winter Haven 33884 Off market since Aug 2026 $299,999 · 3 bd · 2 ba · 1,645 sqft
- 1799 carnostie road, Winter Haven 33884 Off market since Sep 2026 $295,000 · 4 bd · 2 ba · 1,680 sqft
- 3316 white indigo road, Winter Haven 33884 Off market since Sep 2026 $292,900 · 3 bd · 2 ba · 1,504 sqft
- 3935 palazzo place, Winter Haven 33884 Off market since Sep 2026 $250,000 · 5 bd · 3 ba · 2,601 sqft
- 111 las flores, Winter Haven 33884 Off market since Sep 2026 $275,000 · 3 bd · 2 ba · 1,639 sqft
- 262 oleander street, Winter Haven 33881 Off market since Sep 2026 $274,900 · 4 bd · 2 ba · 1,743 sqft
- 1022 northwest 30th street, Winter Haven 33881 Off market since Jul 2026 $250,000 · 3 bd · 1 ba · 1,129 sqft
- 4019 carteret drive, Winter Haven 33884 Off market since Aug 2026 $262,500 · 2 bd · 2 ba · 1,719 sqft
- 638 lake dexter circle, Winter Haven 33884 Off market since Sep 2026 $239,900 · 3 bd · 2 ba · 1,316 sqft
- 5445 chandler drive, Winter Haven 33884 Off market since Sep 2026 $290,000 · 4 bd · 3 ba · 3,010 sqft
- 221 avenue l northeast, Winter Haven 33881 Off market since Jul 2026 $226,000 · 3 bd · 3 ba · 1,000 sqft
- 2790 adeline avenue, Winter Haven 33881 Off market since Sep 2026 $269,900 · 3 bd · 2 ba · 1,328 sqft
- 1678 linz court, Winter Haven 33884 Off market since Sep 2026 $245,000 · 2 bd · 2 ba · 1,158 sqft
- 1450 west lake cannon drive northwest, Winter Haven 33881 Off market since Sep 2026 $299,000 · 5 bd · 2 ba · 4,053 sqft
- 6332 bayberry boulevard northeast, Winter Haven 33881 Off market since Jul 2026 $106,000 · 2 bd · 2 ba · 1,012 sqft
- 1015 carefree cove drive, Winter Haven 33881 Off market since Sep 2026 $204,900 · 4 bd · 2 ba · 1,104 sqft
- 28 casarena court, Winter Haven 33881 Off market since Sep 2026 $135,000 · 2 bd · 3 ba · 2,045 sqft
- 357 squires grove drive, Winter Haven 33880 Off market since Sep 2026 $244,900 · 3 bd · 2 ba · 1,616 sqft
- 1727 second street northeast, Winter Haven 33881 Off market since Sep 2026 $260,000 · 3 bd · 2 ba · 1,470 sqft
- 1629 nantucket way, Winter Haven 33884 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,526 sqft
- 121 bates avenue southeast, Winter Haven 33880 Off market since Sep 2026 $179,000 · 2 bd · 1 ba · 1,080 sqft
- 5125 sylas jax avenue, Winter Haven 33884 Off market since Sep 2026 $259,900 · 3 bd · 2 ba · 1,358 sqft