Homes under $300K in Winter Haven, FL

452 homes for sale · Updated August 12, 2026 · Page 1 of 10

• 5850 cypress gardens boulevard 304, Winter Haven 33884 $139,000 · 2 bd · 2 ba · 1,332 sqft
• 508 lakeside ranch way, Winter Haven 33881 $79,000 · 2 bd · 2 ba · 1,128 sqft
• 657 ave c southwest, Winter Haven 33880 $250,000 · 3 bd · 2 ba · 1,144 sqft
• 100 lakeside ranch drive, Winter Haven 33881 $120,000 · 2 bd · 2 ba · 1,176 sqft
• 6308 bayberry boulevard northeast, Winter Haven 33881 $155,700 · 2 bd · 2 ba · 1,152 sqft
• 1561 vienna square drive, Winter Haven 33884 $229,500 · 2 bd · 2 ba · 1,231 sqft
• 1787 white elephant loop, Winter Haven 33884 $279,900 · 3 bd · 2 ba · 1,526 sqft
• 441 san jose drive, Winter Haven 33884 $275,000 · 2 bd · 2 ba · 1,843 sqft
• 700 mirror terrace northwest 303, Winter Haven 33881 $99,900 · 2 bd · 2 ba · 1,029 sqft
• 6107 grand oaks drive southeast, Winter Haven 33884 $179,900 · 2 bd · 2 ba · 1,340 sqft
• 4321 cherrywood street, Winter Haven 33880 $108,000 · 2 bd · 2 ba · 1,488 sqft
• 6044 grand oaks drive southeast, Winter Haven 33884 $145,000 · 2 bd · 2 ba · 1,248 sqft
• 689 lake howard drive northwest 1e, Winter Haven 33880 $124,000 · 2 bd · 2 ba · 1,050 sqft
• 235 hibiscus street, Winter Haven 33881 $280,000 · 5 bd · 3 ba · 2,527 sqft
• 123 osprey heights drive, Winter Haven 33880 $250,000 · 3 bd · 2 ba · 1,329 sqft
• 683 broadmoor circle 683, Winter Haven 33884 $198,000 · 2 bd · 2 ba · 1,139 sqft
• 2218 abbey road, Winter Haven 33880 $179,999 · 2 bd · 2 ba · 1,252 sqft
• 1703 linz court, Winter Haven 33884 $259,000 · 2 bd · 2 ba · 1,164 sqft
• 1224 vienna square drive, Winter Haven 33884 $225,000 · 2 bd · 2 ba · 1,118 sqft
• 3931 avenue r northwest, Winter Haven 33881 $185,000 · 3 bd · 2 ba · 928 sqft
• 912 avenue t southeast, Winter Haven 33880 $295,000 · 3 bd · 2 ba · 2,149 sqft
• 215 10th wahneta street west, Winter Haven 33880 $145,088 · 3 bd · 2 ba · 800 sqft
• 119 allen avenue, Winter Haven 33880 $250,000 · 4 bd · 2 ba · 1,520 sqft
• 4246 cedarwood street, Winter Haven 33880 $105,000 · 2 bd · 2 ba · 1,008 sqft
• 95 parson drive, Winter Haven 33884 $75,000 · 3 bd · 2 ba · 1,176 sqft
• 14 enclave drive, Winter Haven 33884 $219,900 · 2 bd · 2 ba · 1,368 sqft
• 6056 navona way, Winter Haven 33884 $259,999 · 3 bd · 2 ba · 1,615 sqft
• 3923 baldwin lane, Winter Haven 33884 $263,900 · 3 bd · 2 ba · 1,719 sqft
• 11 casarena court, Winter Haven 33881 $230,000 · 2 bd · 3 ba · 2,045 sqft
• 2817 wingfoot court, Winter Haven 33884 $270,000 · 3 bd · 2 ba · 1,666 sqft
• 1414 26th street northwest, Winter Haven 33881 $239,000 · 3 bd · 2 ba · 1,102 sqft
• 1012 medinah drive southeast, Winter Haven 33884 $187,900 · 2 bd · 2 ba · 1,458 sqft
• 1109 5th street southwest, Winter Haven 33880 $195,000 · 3 bd · 2 ba · 1,238 sqft
• 1997 26th street northwest, Winter Haven 33881 $194,900 · 3 bd · 2 ba · 1,166 sqft
• 1709 linz court, Winter Haven 33884 $259,000 · 2 bd · 2 ba · 1,164 sqft
• 3715 avenue j northwest, Winter Haven 33881 $217,000 · 3 bd · 2 ba · 892 sqft
• 913 eagle rock terrace, Winter Haven 33880 $289,500 · 4 bd · 2 ba · 1,728 sqft
• 4127 sprucewood street, Winter Haven 33880 $85,000 · 2 bd · 2 ba · 1,035 sqft
• 3843 eloise estates court, Winter Haven 33881 $280,000 · 3 bd · 2 ba · 1,600 sqft
• 1740 2nd street northeast, Winter Haven 33881 $225,000 · 3 bd · 2 ba · 1,683 sqft
• 649 broadmoor circle, Winter Haven 33884 $137,500 · 2 bd · 2 ba · 1,278 sqft
• 2307 scarlet avenue, Winter Haven 33884 $260,000 · 3 bd · 2 ba · 1,343 sqft
• 1601 roselawn street southwest, Winter Haven 33880 $256,500 · 2 bd · 1 ba · 1,099 sqft
• 6033 grand oaks drive southeast, Winter Haven 33884 $129,900 · 2 bd · 2 ba · 1,120 sqft
• 400 el camino drive 223, Winter Haven 33884 $59,900 · 1 bd · 1 ba · 850 sqft
• 200 black skimmer lane, Winter Haven 33880 $285,000 · 3 bd · 2 ba · 1,265 sqft
• 6315 grove pointe drive southeast, Winter Haven 33884 $158,000 · 2 bd · 2 ba · 1,248 sqft
• 5580 state road 542 west, Winter Haven 33880 $235,000 · 4 bd · 3 ba · 2,174 sqft
• 2739 rutledge court, Winter Haven 33884 $215,000 · 3 bd · 2 ba · 1,419 sqft
• 1864 emily drive, Winter Haven 33884 $289,900 · 4 bd · 2 ba · 1,836 sqft