Homes under $300K in Winter Haven, FL

333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 5 of 23

• 6825 south lake henry drive northeast, Winter Haven 33881 $220,000 · 2 bd · 2 ba · 1,790 sqft
• 1776 6th street northwest #504, Winter Haven 33881 $147,500 · 2 bd · 2 ba · 1,347 sqft
• 3923 baldwin lane, Winter Haven 33884 $253,900 · 3 bd · 2 ba · 1,719 sqft
• 884 cambridge drive, Winter Haven 33881 $279,000 · 4 bd · 3 ba · 2,368 sqft
• 3334 avenue j northwest, Winter Haven 33881 $249,765 · 3 bd · 2 ba · 1,473 sqft
• 2925 dayton drive, Winter Haven 33884 $284,500 · 3 bd · 2 ba · 2,109 sqft
• 2415 brassie court, Winter Haven 33884 $289,900 · 3 bd · 2 ba · 1,629 sqft
• 447 san jose drive, Winter Haven 33884 $224,900 · 2 bd · 2 ba · 1,600 sqft
• 4242 cedarwood street, Winter Haven 33880 $110,000 · 2 bd · 2 ba · 1,056 sqft
• 602 taylor boulevard, Winter Haven 33880 $220,000 · 3 bd · 2 ba · 1,242 sqft
• 1333 lucerne loop road northeast, Winter Haven 33881 $259,000 · 4 bd · 2 ba · 1,746 sqft
• 1711 garden lake drive #1711, Winter Haven 33884 $170,000 · 1 bd · 1 ba · 828 sqft
• 1776 6th street northwest #308, Winter Haven 33881 $144,900 · 2 bd · 2 ba · 1,347 sqft
• 1776 6th street northwest #409, Winter Haven 33881 $119,000 · 2 bd · 2 ba · 1,347 sqft
• 700 mirror terrace northwest #506, Winter Haven 33881 $119,000 · 2 bd · 2 ba · 1,190 sqft
• 7158 summit place, Winter Haven 33884 $299,000 · 4 bd · 2 ba · 1,833 sqft
• 136 lake ring drive, Winter Haven 33884 $299,900 · 3 bd · 2 ba · 1,728 sqft
• 6204 knotty pine drive southeast, Winter Haven 33884 $165,000 · 2 bd · 2 ba · 1,014 sqft
• 1799 carnostie road, Winter Haven 33884 $295,000 · 4 bd · 2 ba · 1,680 sqft
• 6773 brentwood drive northeast, Winter Haven 33881 $139,900 · 2 bd · 2 ba · 1,056 sqft
• 4918 rosewood street, Winter Haven 33880 $125,000 · 2 bd · 2 ba · 1,008 sqft
• 214 king road, Winter Haven 33880 $249,900 · 3 bd · 2 ba · 1,124 sqft
• 323 orange blossom drive #323, Winter Haven 33880 $205,000 · 2 bd · 3 ba · 1,280 sqft
• 707 dolly ben court, Winter Haven 33880 $239,000 · 3 bd · 1 ba · 1,048 sqft
• 4155 sprucewood street, Winter Haven 33880 $115,000 · 2 bd · 2 ba · 1,200 sqft
• 100 el camino drive #104, Winter Haven 33884 $179,900 · 3 bd · 2 ba · 1,579 sqft
• 14 enclave drive, Winter Haven 33884 $219,900 · 2 bd · 2 ba · 1,368 sqft
• 1709 linz court, Winter Haven 33884 $248,000 · 2 bd · 2 ba · 1,164 sqft
• 232 kings pond avenue, Winter Haven 33880 $294,990 · 3 bd · 2 ba · 1,417 sqft
• 233 kings pond avenue, Winter Haven 33880 $264,950 · 3 bd · 2 ba · 1,220 sqft
• 2801 wingfoot court, Winter Haven 33884 $249,900 · 2 bd · 2 ba · 1,666 sqft
• 213 10th wahneta street west, Winter Haven 33880 $145,999 · 2 bd · 1 ba · 826 sqft
• 5780 lakeside landings boulevard, Winter Haven 33881 $299,900 · 4 bd · 3 ba · 2,526 sqft
• 5638 royal hills street, Winter Haven 33881 $299,500 · 4 bd · 2 ba · 2,012 sqft
• 4116 fishermans landing, Winter Haven 33884 $237,900 · 3 bd · 2 ba · 1,313 sqft
• 813 eagle rock terrace, Winter Haven 33880 $255,000 · 3 bd · 2 ba · 1,292 sqft
• 7041 fairview village circle, Winter Haven 33881 $57,900 · 2 bd · 1 ba · 248 sqft
• 111 sunset drive east, Winter Haven 33881 $190,000 · 4 bd · 1 ba · 2,078 sqft
• 2338 salzburg loop, Winter Haven 33884 $198,000 · 2 bd · 2 ba · 1,246 sqft
• 1703 linz court, Winter Haven 33884 $248,000 · 2 bd · 2 ba · 1,164 sqft
• 1776 6th street northwest #304, Winter Haven 33881 $98,500 · 2 bd · 2 ba · 1,347 sqft
• 2211 9th street northeast, Winter Haven 33881 $220,000 · 3 bd · 2 ba · 1,522 sqft
• 1945 8th street southeast, Winter Haven 33880 $225,000 · 2 bd · 2 ba · 1,787 sqft
• 851 avenue r northeast, Winter Haven 33881 $249,900 · 3 bd · 2 ba · 1,384 sqft
• 809 magnolia place, Winter Haven 33884 $235,000 · 2 bd · 2 ba · 1,308 sqft
• 6 golfview circle northeast, Winter Haven 33881 $299,900 · 3 bd · 3 ba · 1,892 sqft
• 4056 rolling oaks drive, Winter Haven 33880 $114,900 · 2 bd · 2 ba · 1,104 sqft
• listing-10673544235, Winter Haven 33884 $260,000 · 4 bd · 3 ba · 2,300 sqft
• 967 lunar lane, Winter Haven 33884 $298,080 · 3 bd · 2 ba · 1,266 sqft
• 508 eagle pond drive #508, Winter Haven 33884 $160,000 · 2 bd · 2 ba · 1,017 sqft