Homes under $500K in Winter Haven, FL
733 homes for sale · Updated August 12, 2026 · Page 1 of 15
- 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
- 1004 avenue g northeast, Winter Haven 33881 $310,000 · 3 bd · 2 ba · 1,398 sqft
- 104 woden way, Winter Haven 33884 $379,000 · 3 bd · 2 ba · 2,218 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
- 4099 island lakes drive, Winter Haven 33881 $379,000 · 3 bd · 2 ba · 1,603 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
- 5135 kinsley drive, Winter Haven 33884 $319,950 · 4 bd · 2 ba · 1,919 sqft
- 5147 kinsley drive, Winter Haven 33884 $323,635 · 4 bd · 2 ba · 1,919 sqft
- 119 allen avenue, Winter Haven 33880 $250,000 · 4 bd · 2 ba · 1,520 sqft
- 621 vittorio drive, Winter Haven 33884 $305,000 · 4 bd · 2 ba · 1,857 sqft
- 3132 country club circle, Winter Haven 33881 $314,900 · 4 bd · 2 ba · 1,851 sqft
- 4246 cedarwood street, Winter Haven 33880 $105,000 · 2 bd · 2 ba · 1,008 sqft
- 5163 kinsley drive, Winter Haven 33884 $339,999 · 4 bd · 3 ba · 2,077 sqft
- 974 lunar lane, Winter Haven 33884 $341,066 · 4 bd · 2 ba · 1,816 sqft
- 959 lunar lane, Winter Haven 33884 $319,532 · 3 bd · 2 ba · 1,730 sqft
- 4273 stafford drive, Winter Haven 33880 $399,900 · 3 bd · 2 ba · 1,475 sqft
- 1908 crossroads boulevard, Winter Haven 33881 $395,000 · 4 bd · 3 ba · 2,781 sqft
- 1340 daisy field drive, Winter Haven 33884 $310,000 · 4 bd · 2 ba · 1,882 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
- 5171 kinsley drive, Winter Haven 33884 $336,899 · 4 bd · 3 ba · 2,050 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