Homes under $300K in Winter Haven, FL
333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 16 of 23
- 4918 rosewood street, Winter Haven 33880 Off market since Sep 2026 $125,000 · 2 bd · 2 ba · 1,008 sqft
- 144 morning glory circle, Winter Haven 33884 Off market since Sep 2026 $279,000 · 3 bd · 2 ba · 1,433 sqft
- 607 country lane northeast 607, Winter Haven 33881 Off market since Sep 2026 $142,500 · 2 bd · 2 ba · 1,252 sqft
- 220 king road, Winter Haven 33880 Off market since Sep 2026 $119,000 · 2 bd · 1 ba · 672 sqft
- 321 orange blossom drive, Winter Haven 33880 Off market since Sep 2026 $199,950 · 2 bd · 3 ba · 1,407 sqft
- 213 cleveland avenue, Winter Haven 33881 Off market since Sep 2026 $180,000 · 2 bd · 1 ba · 728 sqft
- 2105 9th street northeast, Winter Haven 33881 Off market since Sep 2026 $239,000 · 3 bd · 1 ba · 1,042 sqft
- 6450 hollyberry lane northeast, Winter Haven 33881 Off market since Sep 2026 $151,000 · 2 bd · 2 ba · 1,144 sqft
- 125 lake hazel drive, Winter Haven 33884 Off market since Sep 2026 $100,000 · 2 bd · 2 ba · 1,056 sqft
- 6773 brentwood drive northeast, Winter Haven 33881 Off market since Sep 2026 $139,900 · 2 bd · 2 ba · 1,056 sqft
- 507 sharon hill court, Winter Haven 33880 Off market since Aug 2026 $254,999 · 4 bd · 2 ba · 2,356 sqft
- 2500 21st street northwest 15, Winter Haven 33881 Off market since Sep 2026 $170,000 · 2 bd · 3 ba · 1,184 sqft
- 1382 salisbury drive, Winter Haven 33881 Off market since Sep 2026 $293,899 · 4 bd · 3 ba · 1,764 sqft
- 6309 grove pointe drive southeast, Winter Haven 33884 Off market since Sep 2026 $154,000 · 2 bd · 2 ba · 1,248 sqft
- 542 eagle landing boulevard, Winter Haven 33880 Off market since Sep 2026 $257,000 · 3 bd · 2 ba · 1,292 sqft
- 4155 sprucewood street, Winter Haven 33880 Off market since Sep 2026 $115,000 · 2 bd · 2 ba · 1,200 sqft
- 961 harold pass, Winter Haven 33884 Off market since Sep 2026 $247,990 · 3 bd · 2 ba · 1,432 sqft
- 204 kingshill court southeast, Winter Haven 33884 Off market since Sep 2026 $254,900 · 3 bd · 2 ba · 1,437 sqft
- 221 avenue f southeast, Winter Haven 33880 Sold on Jul 7, 2026 $185,000 · 2 bd · 2 ba · 804 sqft
- 6473 peppertree path northeast, Winter Haven 33881 Off market since Sep 2026 $146,000 · 2 bd · 2 ba · 1,107 sqft
- 4173 rolling oaks drive, Winter Haven 33880 Off market since Sep 2026 $95,000 · 2 bd · 2 ba · 720 sqft
- 231 avenue a northeast, Winter Haven 33881 Off market since Sep 2026 $195,000 · 3 bd · 1 ba · 1,144 sqft
- 4925 cypress gardens road 100, Winter Haven 33884 Off market since Jul 2026 $195,000 · 2 bd · 2 ba · 1,008 sqft
- 851 vienna drive, Winter Haven 33884 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,569 sqft
- 4140 sophia boulevard, Winter Haven 33880 Off market since Sep 2026 $255,000 · 3 bd · 2 ba · 1,711 sqft
- 292 arbuthnot street, Winter Haven 33881 Off market since Jul 2026 $299,900 · 3 bd · 2 ba · 1,305 sqft
- 2415 brassie court, Winter Haven 33884 Off market since Sep 2026 $289,900 · 3 bd · 2 ba · 1,629 sqft
- 1619 pearce road northwest, Winter Haven 33881 Off market since Sep 2026 $265,000 · 2 bd · 1 ba · 2,142 sqft
- 113 6th jpv street, Winter Haven 33880 Off market since Sep 2026 $250,000 · 3 bd · 2 ba · 1,035 sqft
- 2128 34th street northwest, Winter Haven 33881 Off market since Jul 2026 $190,000 · 4 bd · 2 ba · 1,437 sqft
- 665 broadmoor circle, Winter Haven 33884 Off market since Jul 2026 $170,000 · 2 bd · 2 ba · 1,139 sqft
- 800 ware avenue northeast, Winter Haven 33881 Off market since Sep 2026 $242,499 · 3 bd · 2 ba · 1,000 sqft
- 447 village circle southwest, Winter Haven 33880 Off market since Sep 2026 $145,000 · 2 bd · 2 ba · 1,000 sqft
- 205 arbuthnot street, Winter Haven 33881 Off market since Jul 2026 $299,777 · 3 bd · 2 ba · 1,447 sqft
- 909 cambridge drive, Winter Haven 33881 Off market since Sep 2026 $256,900 · 3 bd · 2 ba · 1,506 sqft
- 3971 cypress landing west, Winter Haven 33884 Off market since Sep 2026 $289,900 · 3 bd · 2 ba · 1,674 sqft
- 3060 captain jax way, Winter Haven 33884 Off market since Aug 2026 $239,990 · 3 bd · 3 ba · 1,423 sqft
- 323 orange blossom drive 323, Winter Haven 33880 Off market since Sep 2026 $205,000 · 2 bd · 3 ba · 1,280 sqft
- 2747 san marco way, Winter Haven 33884 Off market since Sep 2026 $284,990 · 3 bd · 2 ba · 1,680 sqft
- 3420 avenue t northwest, Winter Haven 33881 Off market since Sep 2026 $225,000 · 3 bd · 3 ba · 1,088 sqft
- 3732 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $250,000 · 4 bd · 2 ba · 1,713 sqft
- 306 palmetto avenue northwest, Winter Haven 33881 Off market since Sep 2026 $179,000 · 3 bd · 1 ba · 768 sqft
- 202 saint lucie road, Winter Haven 33884 Off market since Sep 2026 $299,900 · 3 bd · 2 ba · 1,764 sqft
- 445 mckenna drive, Winter Haven 33881 Off market since Sep 2026 $299,000 · 4 bd · 2 ba · 1,694 sqft
- 2130 34th street northwest, Winter Haven 33881 Sold on Jul 10, 2026 $135,000 · 3 bd · 1 ba · 1,068 sqft
- 4038 rolling oaks drive, Winter Haven 33880 Off market since Sep 2026 $74,900 · 2 bd · 2 ba · 1,056 sqft
- 6114 grand oaks drive southeast, Winter Haven 33884 Off market since Sep 2026 $159,900 · 2 bd · 2 ba · 1,288 sqft
- 825 northwest avenue y avenue northwest, Winter Haven 33881 Off market since Aug 2026 $285,000 · 3 bd · 1 ba · 1,497 sqft
- 300 avenue v northeast, Winter Haven 33881 Off market since Sep 2026 $165,000 · 3 bd · 1 ba · 912 sqft
- 128 avenue d southwest, Winter Haven 33880 Off market since Sep 2026 $175,000 · 5 bd · 2 ba · 2,200 sqft