Homes under $500K in Winter Haven, FL
718 for sale · 1,258 homes listed · Updated September 25, 2026 · Page 1 of 26
- 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
- 821 sun burst road, Winter Haven 33880 $360,000 · 5 bd · 3 ba · 2,601 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
- 1561 vienna square drive, Winter Haven 33884 $225,000 · 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
- 503 holt circle, Winter Haven 33880 $170,000 · 3 bd · 2 ba · 1,305 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 $274,400 · 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 $193,000 · 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 $248,000 · 2 bd · 2 ba · 1,164 sqft
- 4099 island lakes drive, Winter Haven 33881 $379,000 · 3 bd · 2 ba · 1,603 sqft
- 934 cattleman street, Winter Haven 33884 $350,000 · 5 bd · 3 ba · 2,215 sqft
- 1224 vienna square drive, Winter Haven 33884 $215,000 · 2 bd · 2 ba · 1,118 sqft
- 3931 avenue r northwest, Winter Haven 33881 $185,000 · 3 bd · 2 ba · 928 sqft
- 5147 kinsley drive, Winter Haven 33884 $324,999 · 4 bd · 2 ba · 1,919 sqft
- 119 allen avenue, Winter Haven 33880 $240,000 · 4 bd · 2 ba · 1,520 sqft
- 621 vittorio drive, Winter Haven 33884 $305,000 · 4 bd · 2 ba · 1,857 sqft
- 4246 cedarwood street, Winter Haven 33880 $99,000 · 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 $375,000 · 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
- 3923 baldwin lane, Winter Haven 33884 $253,900 · 3 bd · 2 ba · 1,719 sqft
- 2817 wingfoot court, Winter Haven 33884 $270,000 · 3 bd · 2 ba · 1,666 sqft
- 601 avenue u northeast, Winter Haven 33881 $199,900 · 2 bd · 1 ba · 1,274 sqft
- 1818 6th street southeast, Winter Haven 33880 $479,000 · 5 bd · 3 ba · 2,006 sqft
- 1997 26th street northwest, Winter Haven 33881 $189,900 · 3 bd · 2 ba · 1,166 sqft
- 1709 linz court, Winter Haven 33884 $248,000 · 2 bd · 2 ba · 1,164 sqft
- 3715 avenue j northwest, Winter Haven 33881 $217,000 · 3 bd · 2 ba · 892 sqft
- 3307 fox ridge drive, Winter Haven 33884 $235,000 · 4 bd · 2 ba · 1,253 sqft
- 136 madera drive, Winter Haven 33880 $171,380 · 3 bd · 2 ba · 1,448 sqft
- 602 taylor boulevard, Winter Haven 33880 $220,000 · 3 bd · 2 ba · 1,242 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
- 126 lake region circle, Winter Haven 33881 $400,000 · 4 bd · 2 ba · 2,142 sqft
- 649 broadmoor circle, Winter Haven 33884 $124,000 · 2 bd · 2 ba · 1,278 sqft
- 757 reggie road, Winter Haven 33884 $303,000 · 3 bd · 2 ba · 1,432 sqft
- 1122 brimstone circle, Winter Haven 33884 $325,000 · 3 bd · 2 ba · 1,690 sqft
- 919 avenue south southeast, Winter Haven 33880 $330,000 · 3 bd · 2 ba · 1,751 sqft