Homes under $300K in Winter Haven, FL
333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 19 of 23
- 204 4th jpv street, Winter Haven 33880 Off market since Jul 2026 $175,000 · 3 bd · 2 ba · 1,068 sqft
- 105 lake sears drive, Winter Haven 33880 Off market since Aug 2026 $279,900 · 3 bd · 2 ba · 1,513 sqft
- 6604 winterset gardens road, Winter Haven 33884 Off market since Jul 2026 $250,000 · 3 bd · 3 ba · 2,459 sqft
- 129 florida drive, Winter Haven 33881 Off market since Jul 2026 $140,000 · 3 bd · 1 ba · 1,088 sqft
- 2711 gladiola road, Winter Haven 33884 Off market since Sep 2026 $254,900 · 3 bd · 3 ba · 1,673 sqft
- 3129 avenue west northwest, Winter Haven 33881 Off market since Sep 2026 $212,000 · 3 bd · 1 ba · 1,500 sqft
- 1525 oakview circle southeast, Winter Haven 33880 Off market since Sep 2026 $199,000 · 2 bd · 2 ba · 1,333 sqft
- 4242 cedarwood street, Winter Haven 33880 Off market since Sep 2026 $110,000 · 2 bd · 2 ba · 1,056 sqft
- 5308 green drive, Winter Haven 33884 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,495 sqft
- 6053 southern oaks drive southeast, Winter Haven 33884 Off market since Jul 2026 $136,900 · 2 bd · 2 ba · 1,104 sqft
- 2216 starboard, Winter Haven 33881 Off market since Sep 2026 $215,000 · 3 bd · 3 ba · 1,549 sqft
- 406 lake daisy drive, Winter Haven 33884 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,406 sqft
- 1405 28th street northwest, Winter Haven 33881 Off market since Sep 2026 $220,000 · 2 bd · 1 ba · 1,137 sqft
- 3319 avenue u northwest, Winter Haven 33881 Off market since Sep 2026 $145,000 · 2 bd · 1 ba · 840 sqft
- 211 golf aire boulevard, Winter Haven 33884 Sold on Jul 21, 2026 $299,900 · 3 bd · 2 ba · 1,650 sqft
- 415 8th street northeast, Winter Haven 33881 Off market since Sep 2026 $255,000 · 3 bd · 2 ba · 1,652 sqft
- 3420 avenue r northwest, Winter Haven 33881 Off market since Sep 2026 $205,000 · 2 bd · 1 ba · 672 sqft
- 715 avenue b southwest, Winter Haven 33880 Off market since Sep 2026 $239,900 · 3 bd · 2 ba · 1,580 sqft
- 2865 whispering trails drive, Winter Haven 33884 Off market since Sep 2026 $234,900 · 3 bd · 2 ba · 1,253 sqft
- 1365 sheridan street southwest, Winter Haven 33880 Off market since Sep 2026 $222,000 · 2 bd · 1 ba · 1,199 sqft
- 1328 3rd street northeast, Winter Haven 33881 Off market since Sep 2026 $199,999 · 3 bd · 2 ba · 1,118 sqft
- 6235 knotty pine drive southeast, Winter Haven 33884 Off market since Sep 2026 $155,000 · 2 bd · 2 ba · 1,080 sqft
- 1 enclave drive, Winter Haven 33884 Off market since Sep 2026 $220,000 · 3 bd · 2 ba · 1,676 sqft
- 428 mckenna drive, Winter Haven 33881 Off market since Sep 2026 $260,000 · 4 bd · 2 ba · 1,840 sqft
- 626 pavare court, Winter Haven 33884 Off market since Sep 2026 $129,900 · 2 bd · 2 ba · 851 sqft
- 233 kensington view boulevard, Winter Haven 33880 Off market since Sep 2026 $270,000 · 3 bd · 2 ba · 1,491 sqft
- 110 morning glory circle, Winter Haven 33884 Off market since Sep 2026 $265,000 · 3 bd · 3 ba · 1,685 sqft
- 308 vaniman avenue, Winter Haven 33880 Off market since Sep 2026 $229,900 · 3 bd · 2 ba · 1,228 sqft
- 5811 marsh landing drive, Winter Haven 33881 Off market since Sep 2026 $269,000 · 3 bd · 2 ba · 1,873 sqft
- 931 summer glen drive, Winter Haven 33880 Off market since Sep 2026 $225,000 · 3 bd · 2 ba · 1,851 sqft
- 7902 waterview way, Winter Haven 33884 Off market since Sep 2026 $189,900 · 2 bd · 2 ba · 930 sqft
- 307 avenue x northeast, Winter Haven 33881 Off market since Sep 2026 $185,000 · 3 bd · 2 ba · 1,200 sqft
- 6666 briarhill drive northeast, Winter Haven 33881 Off market since Sep 2026 $140,000 · 2 bd · 2 ba · 1,144 sqft
- 1628 hummingbird road, Winter Haven 33884 Sold on Aug 14, 2026 $284,900 · 3 bd · 2 ba · 1,593 sqft
- 333 lake howard drive northwest 211b, Winter Haven 33880 Off market since Sep 2026 $149,900 · 3 bd · 2 ba · 1,218 sqft
- 444 avenue b northeast, Winter Haven 33881 Off market since Sep 2026 $179,000 · 4 bd · 2 ba · 1,464 sqft
- 3856 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $259,000 · 3 bd · 2 ba · 1,288 sqft
- 709 sarner pass way, Winter Haven 33881 Off market since Sep 2026 $279,900 · 4 bd · 3 ba · 3,016 sqft
- 706 avenue i northeast, Winter Haven 33881 Off market since Sep 2026 $295,000 · 3 bd · 2 ba · 1,925 sqft
- 1776 6th street northwest 807, Winter Haven 33881 Off market since Sep 2026 $162,000 · 2 bd · 2 ba · 1,347 sqft
- 221 avenue c northeast, Winter Haven 33881 Off market since Sep 2026 $215,000 · 3 bd · 2 ba · 720 sqft
- 139 avenue g southeast, Winter Haven 33880 Off market since Sep 2026 $180,000 · 2 bd · 1 ba · 896 sqft
- 629 avenue a northeast, Winter Haven 33881 Off market since Sep 2026 $225,000 · 2 bd · 2 ba · 1,293 sqft
- 1700 6th street northwest a38, Winter Haven 33881 Off market since Sep 2026 $78,800 · 2 bd · 1 ba · 840 sqft
- 362 holly ridge road, Winter Haven 33880 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,355 sqft
- 5 moonlight lane, Winter Haven 33884 Off market since Sep 2026 $215,000 · 2 bd · 2 ba · 952 sqft
- 4 enclave drive, Winter Haven 33884 Off market since Sep 2026 $240,000 · 3 bd · 2 ba · 1,526 sqft
- 4919 st james drive, Winter Haven 33881 Off market since Sep 2026 $299,900 · 3 bd · 2 ba · 1,577 sqft
- 5203 waterview way 5203, Winter Haven 33884 Off market since Sep 2026 $159,900 · 2 bd · 2 ba · 930 sqft
- 1903 3rd street northeast, Winter Haven 33881 Off market since Sep 2026 $160,000 · 3 bd · 1 ba · 988 sqft