Homes under $500K in Winter Haven, FL

540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 8 of 36

• 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
• 906 avenue m southeast, Winter Haven 33880 $349,900 · 3 bd · 2 ba · 1,890 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
• 2112 avenue c southwest, Winter Haven 33880 $379,000 · 4 bd · 2 ba · 2,011 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
• 4075 bedford avenue, Winter Haven 33884 $349,001 · 2 bd · 2 ba · 1,888 sqft
• 754 santa maria drive, Winter Haven 33884 $370,000 · 4 bd · 3 ba · 2,200 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
• 1196 lake elbert drive southeast, Winter Haven 33880 $459,900 · 5 bd · 3 ba · 2,242 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
• 845 avenue f northeast, Winter Haven 33881 $309,900 · 3 bd · 2 ba · 1,552 sqft
• listing-10673544235, Winter Haven 33884 $260,000 · 4 bd · 3 ba · 2,300 sqft
• 1531 fuji court, Winter Haven 33881 $440,000 · 4 bd · 3 ba · 3,058 sqft
• 4840 old lucerne park road, Winter Haven 33881 $415,000 · 3 bd · 2 ba · 1,927 sqft
• 967 lunar lane, Winter Haven 33884 $298,080 · 3 bd · 2 ba · 1,266 sqft
• 3971 island lakes drive, Winter Haven 33881 $434,900 · 3 bd · 2 ba · 2,023 sqft
• 508 eagle pond drive #508, Winter Haven 33884 $160,000 · 2 bd · 2 ba · 1,017 sqft
• 2796 whispering trails drive, Winter Haven 33884 $190,000 · 3 bd · 2 ba · 1,158 sqft
• 683 broadmoor circle #683, Winter Haven 33884 $193,000 · 2 bd · 2 ba · 1,139 sqft
• 664 clubhouse road, Winter Haven 33884 $229,000 · 2 bd · 2 ba · 1,395 sqft
• 10 enclave drive, Winter Haven 33884 $214,900 · 2 bd · 2 ba · 1,368 sqft
• 239 golf aire boulevard, Winter Haven 33884 $349,999 · 3 bd · 3 ba · 2,263 sqft
• 2436 edwin street northeast, Winter Haven 33881 $218,994 · 4 bd · 2 ba · 1,813 sqft
• 1268 salisbury drive, Winter Haven 33881 $255,000 · 3 bd · 2 ba · 1,728 sqft
• 1658 teagan lane, Winter Haven 33884 $315,990 · 4 bd · 3 ba · 1,933 sqft
• 567 eagle landing boulevard, Winter Haven 33880 $375,000 · 4 bd · 3 ba · 2,193 sqft
• 6666 briarhill drive northeast, Winter Haven 33881 $140,000 · 2 bd · 2 ba · 1,144 sqft
• 621 vittorio drive, Winter Haven 33884 $305,000 · 4 bd · 2 ba · 1,857 sqft
• 125 edgewater drive, Winter Haven 33881 $210,000 · 4 bd · 3 ba · 1,703 sqft
• 940 oleander drive southeast, Winter Haven 33880 $250,000 · 2 bd · 2 ba · 1,527 sqft
• 3268 country walk club circle, Winter Haven 33881 $295,000 · 3 bd · 2 ba · 1,690 sqft
• 2849 cathy boulevard, Winter Haven 33880 $325,000 · 4 bd · 2 ba · 1,928 sqft
• 1871 emily drive, Winter Haven 33884 $304,900 · 4 bd · 2 ba · 2,012 sqft
• 563 honey bell road, Winter Haven 33880 $299,900 · 4 bd · 2 ba · 1,851 sqft
• 1701 36th street northwest, Winter Haven 33881 $257,999 · 4 bd · 2 ba · 1,815 sqft