Homes under $300K in Winter Haven, FL

333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 20 of 23

1831 carnostie road, Winter Haven 33884 Off market since Sep 2026 $278,000 · 4 bd · 2 ba · 1,680 sqft
3915 avenue q northwest, Winter Haven 33881 Off market since Sep 2026 $109,900 · 3 bd · 2 ba · 860 sqft
200 el camino drive 306, Winter Haven 33884 Off market since Sep 2026 $94,900 · 1 bd · 1 ba · 1,078 sqft
2753 gladiola road, Winter Haven 33884 Off market since Sep 2026 $263,990 · 3 bd · 3 ba · 1,673 sqft
2759 gladiola road, Winter Haven 33884 Off market since Sep 2026 $263,990 · 3 bd · 3 ba · 1,673 sqft
2765 gladiola road, Winter Haven 33884 Off market since Sep 2026 $263,990 · 3 bd · 3 ba · 1,673 sqft
3460 julius estates boulevard, Winter Haven 33881 Off market since Jul 2026 $170,000 · 3 bd · 2 ba · 2,013 sqft
2470 salzburg loop, Winter Haven 33884 Off market since Sep 2026 $280,000 · 3 bd · 2 ba · 1,935 sqft
2021 oliver place, Winter Haven 33881 Off market since Sep 2026 $274,990 · 3 bd · 2 ba · 1,507 sqft
392 kensington view drive, Winter Haven 33880 Off market since Sep 2026 $255,000 · 3 bd · 2 ba · 1,258 sqft
700 mirror terrace northwest 511, Winter Haven 33881 Off market since Sep 2026 $149,900 · 2 bd · 2 ba · 1,190 sqft
1700 6th street northwest c24, Winter Haven 33881 Off market since Sep 2026 $92,000 · 2 bd · 1 ba · 840 sqft
297 meadowbrook boulevard, Winter Haven 33881 Off market since Sep 2026 $230,000 · 3 bd · 2 ba · 1,426 sqft
2435 5th street northeast, Winter Haven 33881 Off market since Aug 2026 $240,000 · 3 bd · 2 ba · 1,215 sqft
235 6th street northwest 307, Winter Haven 33881 Off market since Sep 2026 $125,000 · 1 bd · 1 ba · 714 sqft
650 9th street northeast, Winter Haven 33881 Off market since Sep 2026 $189,900 · 2 bd · 2 ba · 1,110 sqft
1973 carnostie road, Winter Haven 33884 Off market since Sep 2026 $237,500 · 4 bd · 2 ba · 1,828 sqft
2508 avenue a southwest, Winter Haven 33880 Off market since Sep 2026 $205,000 · 3 bd · 1 ba · 850 sqft
1320 normandy heights circle, Winter Haven 33880 Off market since Sep 2026 $245,000 · 3 bd · 2 ba · 1,252 sqft
156 manseau drive, Winter Haven 33880 Off market since Sep 2026 $299,998 · 3 bd · 2 ba · 1,323 sqft
1705 sandalwood circle southwest, Winter Haven 33880 Off market since Sep 2026 $289,900 · 3 bd · 2 ba · 1,164 sqft
109 2nd jpv street, Winter Haven 33880 Off market since Sep 2026 $250,000 · 3 bd · 1 ba · 1,040 sqft
1536 axel circle, Winter Haven 33880 Sold on Aug 3, 2026 $280,000 · 4 bd · 2 ba
3334 avenue j northwest, Winter Haven 33881 Off market since Sep 2026 $249,765 · 3 bd · 2 ba · 1,473 sqft
1500 avenue h northeast, Winter Haven 33881 Off market since Sep 2026 $224,500 · 4 bd · 2 ba · 1,784 sqft
4807 plumwood street, Winter Haven 33880 Off market since Sep 2026 $110,000 · 2 bd · 2 ba · 1,104 sqft
2519 avenue east southwest, Winter Haven 33880 Off market since Sep 2026 $299,900 · 3 bd · 2 ba · 1,675 sqft
2523 avenue east southwest, Winter Haven 33880 Off market since Sep 2026 $298,900 · 3 bd · 2 ba · 1,930 sqft
3328 white indigo road, Winter Haven 33884 Off market since Sep 2026 $276,900 · 3 bd · 2 ba · 1,302 sqft
1100 martinique drive 106, Winter Haven 33884 Off market since Sep 2026 $129,500 · 2 bd · 1 ba · 826 sqft
665 broadmoor circle, Winter Haven 33884 Off market since Sep 2026 $165,000 · 2 bd · 2 ba · 1,139 sqft
1103 cypress gardens boulevard 13, Winter Haven 33884 Off market since Sep 2026 $124,800 · 1 bd · 1 ba · 475 sqft
790 avenue q southeast, Winter Haven 33880 Off market since Sep 2026 $185,000 · 2 bd · 1 ba · 934 sqft
2710 woodlawn drive, Winter Haven 33881 Off market since Sep 2026 $199,000 · 3 bd · 1 ba · 1,092 sqft
5580 taverna loop, Winter Haven 33884 Off market since Sep 2026 $269,990 · 3 bd · 2 ba · 1,302 sqft
296 meredith boulevard, Winter Haven 33881 Off market since Sep 2026 $289,990 · 4 bd · 2 ba · 1,625 sqft
113 lake hazel drive, Winter Haven 33884 Off market since Sep 2026 $115,000 · 2 bd · 2 ba · 1,368 sqft
434 avenue d southeast, Winter Haven 33880 Off market since Sep 2026 $209,000 · 2 bd · 1 ba · 900 sqft
5584 taverna loop, Winter Haven 33884 Off market since Sep 2026 $281,990 · 3 bd · 2 ba · 1,504 sqft
1105 eagle pond drive 1105, Winter Haven 33884 Off market since Sep 2026 $165,000 · 2 bd · 2 ba · 1,017 sqft
306 fern road, Winter Haven 33880 Off market since Sep 2026 $229,900 · 4 bd · 2 ba · 1,599 sqft
4052 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $276,900 · 3 bd · 2 ba · 1,504 sqft
851 avenue r northeast, Winter Haven 33881 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,384 sqft
4332 cherrywood street, Winter Haven 33880 Off market since Aug 2026 $125,000 · 2 bd · 2 ba · 1,150 sqft
2363 gerber dairy road, Winter Haven 33880 Off market since Sep 2026 $220,000 · 3 bd · 2 ba · 1,620 sqft
107 lake elizabeth drive b, Winter Haven 33884 Off market since Sep 2026 $119,000 · 1 bd · 1 ba · 625 sqft
3004 avenue south northwest, Winter Haven 33881 Off market since Sep 2026 $219,900 · 3 bd · 2 ba · 1,153 sqft
1207 32nd street northwest, Winter Haven 33881 Off market since Sep 2026 $229,000 · 3 bd · 1 ba · 1,189 sqft
1557 north lake shipp drive southwest, Winter Haven 33880 Off market since Sep 2026 $264,900 · 3 bd · 2 ba · 1,172 sqft
3941 warbler drive, Winter Haven 33880 Off market since Sep 2026 $234,900 · 4 bd · 3 ba · 1,936 sqft