Homes under $300K in Winter Haven, FL
418 for sale · 1,002 homes listed · Updated November 9, 2026 · Page 2 of 21
- 357 Squires Grove Drive, Winter Haven 33880 $244,900 · 3 bd · 2 ba · 1,616 sqft
- 1207 32nd Street Northwest, Winter Haven 33881 $225,000 · 3 bd · 1 ba · 1,189 sqft
- 1700 6th Street Northwest #C31, Winter Haven 33881 $99,900 · 2 bd · 2 ba · 840 sqft
- 139 Avenue G Southeast, Winter Haven 33880 $170,000 · 2 bd · 1 ba · 896 sqft
- 217 4th Jpv Street, Winter Haven 33880 $214,000 · 3 bd · 1 ba · 1,064 sqft
- 410 Laurel Cove Way, Winter Haven 33884 $209,000 · 2 bd · 2 ba · 1,090 sqft
- 1015 Carefree Cove Drive, Winter Haven 33881 $199,900 · 4 bd · 2 ba · 1,104 sqft
- 3339 Queens Cove Loop, Winter Haven 33880 $234,900 · 3 bd · 2 ba · 1,158 sqft
- 4246 Cedarwood Street, Winter Haven 33880 $99,000 · 2 bd · 2 ba · 1,008 sqft
- 820 26th Street Northwest, Winter Haven 33881 $249,000 · 3 bd · 2 ba · 1,122 sqft
- 8304 Waterview Way #8304, Winter Haven 33884 $154,900 · 2 bd · 2 ba · 930 sqft
- 333 Lake Howard Drive Northwest #211b, Winter Haven 33880 $149,900 · 3 bd · 2 ba · 1,218 sqft
- 105 Laurel Cove Way #105, Winter Haven 33884 $189,000 · 2 bd · 2 ba · 1,090 sqft
- 265 Majestic Gardens Lane, Winter Haven 33880 $294,999 · 3 bd · 2 ba · 1,951 sqft
- 4919 St James Drive, Winter Haven 33881 $294,900 · 3 bd · 2 ba · 1,577 sqft
- 2362 Brassie Court, Winter Haven 33884 $265,000 · 3 bd · 2 ba · 1,260 sqft
- 116 Harbor Drive, Winter Haven 33881 $289,900 · 4 bd · 2 ba · 1,476 sqft
- 790 Avenue Q Southeast, Winter Haven 33880 $185,000 · 2 bd · 1 ba · 934 sqft
- 218 5th Jpv Street, Winter Haven 33880 $223,900 · 5 bd · 2 ba · 1,240 sqft
- 4129 Giorgio Drive, Winter Haven 33884 $276,400 · 3 bd · 2 ba · 1,504 sqft
- 4049 Giorgio Drive, Winter Haven 33884 $281,400 · 3 bd · 2 ba · 1,504 sqft
- 5308 Green Drive, Winter Haven 33884 $245,000 · 3 bd · 2 ba · 1,495 sqft
- 6600 Scenic Point Drive Southeast, Winter Haven 33884 $220,000 · 2 bd · 2 ba · 1,664 sqft
- 1499 Avenue East Northeast, Winter Haven 33881 $245,000 · 3 bd · 1 ba · 1,508 sqft
- 638 Lake Dexter Circle, Winter Haven 33884 $234,900 · 3 bd · 2 ba · 1,316 sqft
- 6022 Grey Heron Drive, Winter Haven 33881 $250,000 · 5 bd · 3 ba · 2,577 sqft
- 1973 Carnostie Road, Winter Haven 33884 $199,000 · 4 bd · 2 ba · 1,828 sqft
- 625 Avenue B Southwest, Winter Haven 33880 $230,000 · 2 bd · 2 ba · 1,240 sqft
- 353 Wharf Way, Winter Haven 33881 $229,900 · 3 bd · 3 ba · 1,604 sqft
- 6114 Grand Oaks Drive Southeast, Winter Haven 33884 $159,900 · 2 bd · 2 ba · 1,288 sqft
- 333 Lake Howard Drive Northwest #302b, Winter Haven 33880 $99,000 · 2 bd · 2 ba · 1,030 sqft
- 333 Lake Howard Drive Northwest #204d, Winter Haven 33880 $139,999 · 3 bd · 2 ba · 1,226 sqft
- 1533 Majestic Lane, Winter Haven 33880 $235,000 · 4 bd · 3 ba · 1,957 sqft
- 2711 Gladiola Road, Winter Haven 33884 $284,490 · 3 bd · 3 ba · 1,673 sqft
- 1103 Cypress Gardens Boulevard #13, Winter Haven 33884 $123,000 · 1 bd · 1 ba · 475 sqft
- 1200 33rd Street Northwest, Winter Haven 33881 $269,900 · 3 bd · 2 ba · 1,138 sqft
- 1500 Avenue H Northeast, Winter Haven 33881 $219,500 · 4 bd · 2 ba · 1,784 sqft
- 679 Avenue L Southeast, Winter Haven 33880 $182,000 · 3 bd · 1 ba · 1,080 sqft
- 4114 Fishermans Landing, Winter Haven 33884 $295,000 · 3 bd · 2 ba · 1,992 sqft
- 4408 Glenns Landing, Winter Haven 33884 $265,000 · 3 bd · 2 ba · 1,668 sqft
- 6364 Lolly Bay Loop Northeast, Winter Haven 33881 $215,000 · 2 bd · 2 ba · 1,143 sqft
- 4160 Giorgio Drive, Winter Haven 33884 $286,400 · 4 bd · 2 ba · 1,665 sqft
- 3328 White Indigo Road, Winter Haven 33884 $287,400 · 3 bd · 2 ba · 1,302 sqft
- 2608 Trinity Circle Northwest, Winter Haven 33881 $239,900 · 2 bd · 2 ba · 1,092 sqft
- 6107 Grand Oaks Drive Southeast, Winter Haven 33884 $168,900 · 2 bd · 2 ba · 1,340 sqft
- 606 Pavare Court #606, Winter Haven 33884 $129,900 · 2 bd · 2 ba · 823 sqft
- 1100 Martinique Drive #203, Winter Haven 33884 $104,900 · 2 bd · 1 ba · 826 sqft
- 665 Broadmoor Circle, Winter Haven 33884 $165,000 · 2 bd · 2 ba · 1,139 sqft
- 503 Sweet Bay Circle, Winter Haven 33884 $224,500 · 2 bd · 2 ba · 1,090 sqft
- 200 El Camino Drive #306, Winter Haven 33884 $83,000 · 1 bd · 1 ba · 1,078 sqft