Homes under $500K in Winter Haven, FL
540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 20 of 36
- 974 lunar lane, Winter Haven 33884 Off market since Sep 2026 $341,066 · 4 bd · 2 ba · 1,816 sqft
- 959 lunar lane, Winter Haven 33884 Off market since Sep 2026 $319,532 · 3 bd · 2 ba · 1,730 sqft
- 4273 stafford drive, Winter Haven 33880 Off market since Sep 2026 $399,900 · 3 bd · 2 ba · 1,475 sqft
- 1908 crossroads boulevard, Winter Haven 33881 Off market since Sep 2026 $375,000 · 4 bd · 3 ba · 2,781 sqft
- 1340 daisy field drive, Winter Haven 33884 Off market since Sep 2026 $310,000 · 4 bd · 2 ba · 1,882 sqft
- 95 parson drive, Winter Haven 33884 Off market since Sep 2026 $75,000 · 3 bd · 2 ba · 1,176 sqft
- 14 enclave drive, Winter Haven 33884 Off market since Sep 2026 $219,900 · 2 bd · 2 ba · 1,368 sqft
- 3923 baldwin lane, Winter Haven 33884 Off market since Sep 2026 $253,900 · 3 bd · 2 ba · 1,719 sqft
- 11 casarena court, Winter Haven 33881 Off market since Sep 2026 $230,000 · 2 bd · 3 ba · 2,045 sqft
- 2817 wingfoot court, Winter Haven 33884 Off market since Sep 2026 $270,000 · 3 bd · 2 ba · 1,666 sqft
- 601 avenue u northeast, Winter Haven 33881 Off market since Sep 2026 $199,900 · 2 bd · 1 ba · 1,274 sqft
- 2638 san marco way, Winter Haven 33884 Off market since Jul 2026 $298,900 · 4 bd · 2 ba · 1,707 sqft
- 5323 mickey avenue, Winter Haven 33884 Off market since Jul 2026 $324,999 · 4 bd · 3 ba · 2,050 sqft
- 847 channing street, Winter Haven 33880 Off market since Jul 2026 $265,000 · 3 bd · 2 ba · 1,478 sqft
- 1414 26th street northwest, Winter Haven 33881 Off market since Aug 2026 $239,000 · 3 bd · 2 ba · 1,102 sqft
- 5171 kinsley drive, Winter Haven 33884 Off market since Sep 2026 $324,999 · 4 bd · 3 ba · 2,050 sqft
- 1012 medinah drive southeast, Winter Haven 33884 Off market since Sep 2026 $187,900 · 2 bd · 2 ba · 1,458 sqft
- 1818 6th street southeast, Winter Haven 33880 Off market since Sep 2026 $479,000 · 5 bd · 3 ba · 2,006 sqft
- 2720 northwest avenue v, Winter Haven 33881 Off market since Jul 2026 $235,000 · 3 bd · 2 ba · 1,333 sqft
- 905 cambridge drive, Winter Haven 33881 Off market since Sep 2026 $339,999 · 4 bd · 3 ba · 2,364 sqft
- 1997 26th street northwest, Winter Haven 33881 Off market since Sep 2026 $189,900 · 3 bd · 2 ba · 1,166 sqft
- 1709 linz court, Winter Haven 33884 Off market since Sep 2026 $248,000 · 2 bd · 2 ba · 1,164 sqft
- 3715 avenue j northwest, Winter Haven 33881 Off market since Sep 2026 $217,000 · 3 bd · 2 ba · 892 sqft
- 2470 salzburg loop, Winter Haven 33884 Off market since Jul 2026 $280,000 · 3 bd · 2 ba · 1,935 sqft
- 3307 fox ridge drive, Winter Haven 33884 Off market since Sep 2026 $235,000 · 4 bd · 2 ba · 1,253 sqft
- 913 eagle rock terrace, Winter Haven 33880 Off market since Sep 2026 $289,500 · 4 bd · 2 ba · 1,728 sqft
- 136 madera drive, Winter Haven 33880 Off market since Sep 2026 $170,380 · 3 bd · 2 ba · 1,448 sqft
- 602 taylor boulevard, Winter Haven 33880 Off market since Sep 2026 $220,000 · 3 bd · 2 ba · 1,242 sqft
- 3843 eloise estates court, Winter Haven 33881 Off market since Sep 2026 $280,000 · 3 bd · 2 ba · 1,600 sqft
- 1740 2nd street northeast, Winter Haven 33881 Off market since Sep 2026 $225,000 · 3 bd · 2 ba · 1,683 sqft
- 126 lake region circle, Winter Haven 33881 Off market since Sep 2026 $400,000 · 4 bd · 2 ba · 2,142 sqft
- 649 broadmoor circle, Winter Haven 33884 Off market since Sep 2026 $122,000 · 2 bd · 2 ba · 1,278 sqft
- 757 reggie road, Winter Haven 33884 Off market since Sep 2026 $303,000 · 3 bd · 2 ba · 1,432 sqft
- 6518 raintree lane northeast, Winter Haven 33881 Off market since Jul 2026 $165,000 · 2 bd · 2 ba · 1,525 sqft
- 1122 brimstone circle, Winter Haven 33884 Off market since Sep 2026 $325,000 · 3 bd · 2 ba · 1,690 sqft
- 919 avenue south southeast, Winter Haven 33880 Off market since Sep 2026 $330,000 · 3 bd · 2 ba · 1,751 sqft
- 2221 20th street northwest, Winter Haven 33881 Off market since Sep 2026 $319,999 · 4 bd · 2 ba · 1,727 sqft
- 335 columbo street, Winter Haven 33880 Off market since Sep 2026 $375,900 · 4 bd · 3 ba · 2,242 sqft
- 605 honey bell road, Winter Haven 33880 Off market since Aug 2026 $349,000 · 5 bd · 3 ba · 2,616 sqft
- 344 alexzander way, Winter Haven 33881 Off market since Sep 2026 $385,000 · 5 bd · 3 ba · 2,696 sqft
- 2307 scarlet avenue, Winter Haven 33884 Off market since Sep 2026 $260,000 · 3 bd · 2 ba · 1,343 sqft
- 1601 roselawn street southwest, Winter Haven 33880 Off market since Sep 2026 $256,500 · 2 bd · 1 ba · 1,099 sqft
- 6033 grand oaks drive southeast, Winter Haven 33884 Off market since Sep 2026 $129,900 · 2 bd · 2 ba · 1,120 sqft
- 5331 mickey avenue, Winter Haven 33884 Off market since Sep 2026 $354,999 · 4 bd · 3 ba · 2,670 sqft
- 21 casarena court, Winter Haven 33881 Off market since Jul 2026 $285,000 · 2 bd · 3 ba · 2,045 sqft
- 400 el camino drive 223, Winter Haven 33884 Off market since Sep 2026 $59,900 · 1 bd · 1 ba · 850 sqft
- 239 golf aire boulevard, Winter Haven 33884 Off market since Sep 2026 $349,999 · 3 bd · 3 ba · 2,263 sqft
- 326 meadowbrook boulevard, Winter Haven 33881 Off market since Sep 2026 $331,995 · 5 bd · 3 ba · 2,696 sqft
- 200 black skimmer lane, Winter Haven 33880 Off market since Sep 2026 $285,000 · 3 bd · 2 ba · 1,265 sqft
- 6315 grove pointe drive southeast, Winter Haven 33884 Off market since Sep 2026 $158,000 · 2 bd · 2 ba · 1,248 sqft