Homes under $300K in Winter Haven, FL

333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 13 of 23

• 806 avenue l southeast, Winter Haven 33880 Active Under Contract $219,900 · 3 bd · 2 ba · 1,397 sqft
• 1429 lucerne loop road northeast, Winter Haven 33881 Active Under Contract $259,000 · 4 bd · 2 ba · 1,746 sqft
• 5850 cypress gardens boulevard 304, Winter Haven 33884 Off market since Sep 2026 $139,000 · 2 bd · 2 ba · 1,332 sqft
• 508 lakeside ranch way, Winter Haven 33881 Off market since Sep 2026 $79,000 · 2 bd · 2 ba · 1,128 sqft
• 1540 avenue c northeast, Winter Haven 33881 Off market since Jul 2026 $245,000 · 3 bd · 2 ba · 1,344 sqft
• 100 lakeside ranch drive, Winter Haven 33881 Off market since Sep 2026 $120,000 · 2 bd · 2 ba · 1,176 sqft
• 1561 vienna square drive, Winter Haven 33884 Off market since Sep 2026 $225,000 · 2 bd · 2 ba · 1,231 sqft
• 1787 white elephant loop, Winter Haven 33884 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,526 sqft
• 441 san jose drive, Winter Haven 33884 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,843 sqft
• 503 holt circle, Winter Haven 33880 Off market since Sep 2026 $160,000 · 3 bd · 2 ba · 1,305 sqft
• 6107 grand oaks drive southeast, Winter Haven 33884 Off market since Sep 2026 $179,900 · 2 bd · 2 ba · 1,340 sqft
• 4321 cherrywood street, Winter Haven 33880 Off market since Sep 2026 $108,000 · 2 bd · 2 ba · 1,488 sqft
• 6044 grand oaks drive southeast, Winter Haven 33884 Off market since Sep 2026 $145,000 · 2 bd · 2 ba · 1,248 sqft
• 689 lake howard drive northwest 1e, Winter Haven 33880 Off market since Sep 2026 $124,000 · 2 bd · 2 ba · 1,050 sqft
• 235 hibiscus street, Winter Haven 33881 Off market since Sep 2026 $274,400 · 5 bd · 3 ba · 2,527 sqft
• 123 osprey heights drive, Winter Haven 33880 Off market since Sep 2026 $250,000 · 3 bd · 2 ba · 1,329 sqft
• 683 broadmoor circle 683, Winter Haven 33884 Off market since Sep 2026 $193,000 · 2 bd · 2 ba · 1,139 sqft
• 2218 abbey road, Winter Haven 33880 Off market since Sep 2026 $179,999 · 2 bd · 2 ba · 1,252 sqft
• 1703 linz court, Winter Haven 33884 Off market since Sep 2026 $248,000 · 2 bd · 2 ba · 1,164 sqft
• 1224 vienna square drive, Winter Haven 33884 Off market since Sep 2026 $215,000 · 2 bd · 2 ba · 1,118 sqft
• 3931 avenue r northwest, Winter Haven 33881 Off market since Sep 2026 $185,000 · 3 bd · 2 ba · 928 sqft
• 912 avenue t southeast, Winter Haven 33880 Off market since Aug 2026 $295,000 · 3 bd · 2 ba · 2,149 sqft
• 215 10th wahneta street west, Winter Haven 33880 Off market since Sep 2026 $145,061 · 3 bd · 2 ba · 800 sqft
• 119 allen avenue, Winter Haven 33880 Off market since Sep 2026 $219,000 · 4 bd · 2 ba · 1,520 sqft
• 1700 6th street northwest a38, Winter Haven 33881 Off market since Jul 2026 $79,800 · 2 bd · 1 ba · 840 sqft
• 4246 cedarwood street, Winter Haven 33880 Off market since Sep 2026 $99,000 · 2 bd · 2 ba · 1,008 sqft
• 95 parson drive, Winter Haven 33884 Off market since Sep 2026 $75,000 · 3 bd · 2 ba · 1,176 sqft
• 14 enclave drive, Winter Haven 33884 Off market since Sep 2026 $219,900 · 2 bd · 2 ba · 1,368 sqft
• 3923 baldwin lane, Winter Haven 33884 Off market since Sep 2026 $253,900 · 3 bd · 2 ba · 1,719 sqft
• 11 casarena court, Winter Haven 33881 Off market since Sep 2026 $230,000 · 2 bd · 3 ba · 2,045 sqft
• 2817 wingfoot court, Winter Haven 33884 Off market since Sep 2026 $270,000 · 3 bd · 2 ba · 1,666 sqft
• 601 avenue u northeast, Winter Haven 33881 Off market since Sep 2026 $199,900 · 2 bd · 1 ba · 1,274 sqft
• 2638 san marco way, Winter Haven 33884 Off market since Jul 2026 $298,900 · 4 bd · 2 ba · 1,707 sqft
• 847 channing street, Winter Haven 33880 Off market since Jul 2026 $265,000 · 3 bd · 2 ba · 1,478 sqft
• 1414 26th street northwest, Winter Haven 33881 Off market since Aug 2026 $239,000 · 3 bd · 2 ba · 1,102 sqft
• 1012 medinah drive southeast, Winter Haven 33884 Off market since Sep 2026 $187,900 · 2 bd · 2 ba · 1,458 sqft
• 2720 northwest avenue v, Winter Haven 33881 Off market since Jul 2026 $235,000 · 3 bd · 2 ba · 1,333 sqft
• 1997 26th street northwest, Winter Haven 33881 Off market since Sep 2026 $189,900 · 3 bd · 2 ba · 1,166 sqft
• 1709 linz court, Winter Haven 33884 Off market since Sep 2026 $248,000 · 2 bd · 2 ba · 1,164 sqft
• 3715 avenue j northwest, Winter Haven 33881 Off market since Sep 2026 $217,000 · 3 bd · 2 ba · 892 sqft
• 2470 salzburg loop, Winter Haven 33884 Off market since Jul 2026 $280,000 · 3 bd · 2 ba · 1,935 sqft
• 3307 fox ridge drive, Winter Haven 33884 Off market since Sep 2026 $235,000 · 4 bd · 2 ba · 1,253 sqft
• 913 eagle rock terrace, Winter Haven 33880 Off market since Sep 2026 $289,500 · 4 bd · 2 ba · 1,728 sqft
• 136 madera drive, Winter Haven 33880 Off market since Sep 2026 $170,380 · 3 bd · 2 ba · 1,448 sqft
• 602 taylor boulevard, Winter Haven 33880 Off market since Sep 2026 $220,000 · 3 bd · 2 ba · 1,242 sqft
• 3843 eloise estates court, Winter Haven 33881 Off market since Sep 2026 $280,000 · 3 bd · 2 ba · 1,600 sqft
• 1740 2nd street northeast, Winter Haven 33881 Off market since Sep 2026 $225,000 · 3 bd · 2 ba · 1,683 sqft
• 649 broadmoor circle, Winter Haven 33884 Off market since Sep 2026 $122,000 · 2 bd · 2 ba · 1,278 sqft
• 6518 raintree lane northeast, Winter Haven 33881 Off market since Jul 2026 $165,000 · 2 bd · 2 ba · 1,525 sqft
• 2307 scarlet avenue, Winter Haven 33884 Off market since Sep 2026 $260,000 · 3 bd · 2 ba · 1,343 sqft