Homes under $500K in Winter Haven, FL
540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 6 of 36
- 1903 3rd street northeast, Winter Haven 33881 $160,000 · 3 bd · 1 ba · 988 sqft
- 1124 sawgrass drive, Winter Haven 33884 $355,000 · 3 bd · 2 ba · 1,917 sqft
- 3023 caneel street, Winter Haven 33884 $235,000 · 2 bd · 2 ba · 1,385 sqft
- 1187 tyler loop, Winter Haven 33884 $350,000 · 5 bd · 3 ba · 2,254 sqft
- 5264 green drive, Winter Haven 33884 $315,000 · 3 bd · 2 ba · 2,011 sqft
- 628 lakeside ranch lane, Winter Haven 33881 $164,800 · 2 bd · 2 ba · 1,325 sqft
- 5 moonlight lane, Winter Haven 33884 $215,000 · 2 bd · 2 ba · 952 sqft
- 126 lake region circle, Winter Haven 33881 $400,000 · 4 bd · 2 ba · 2,142 sqft
- 4273 stafford drive, Winter Haven 33880 $399,900 · 3 bd · 2 ba · 1,475 sqft
- 125 lake hazel drive, Winter Haven 33884 $100,000 · 2 bd · 2 ba · 1,056 sqft
- 300 greenfield road, Winter Haven 33884 $425,000 · 4 bd · 3 ba · 2,350 sqft
- 5163 kinsley drive, Winter Haven 33884 $339,999 · 4 bd · 3 ba · 2,077 sqft
- 757 reggie road, Winter Haven 33884 $303,000 · 3 bd · 2 ba · 1,432 sqft
- 4599 reynosa drive southwest, Winter Haven 33880 $309,999 · 3 bd · 2 ba · 2,309 sqft
- 187 sweet circle, Winter Haven 33884 $75,000 · 2 bd · 2 ba · 864 sqft
- 3960 giorgio drive, Winter Haven 33884 $289,000 · 4 bd · 2 ba · 1,607 sqft
- 3964 giorgio drive, Winter Haven 33884 $325,000 · 4 bd · 3 ba · 2,387 sqft
- 3972 giorgio drive, Winter Haven 33884 $315,000 · 4 bd · 3 ba · 2,168 sqft
- 3928 giorgio drive, Winter Haven 33884 $279,150 · 4 bd · 2 ba · 1,607 sqft
- 5888 windridge drive, Winter Haven 33881 $330,000 · 4 bd · 3 ba · 2,836 sqft
- 6235 knotty pine drive southeast, Winter Haven 33884 $155,000 · 2 bd · 2 ba · 1,080 sqft
- 601 avenue u northeast, Winter Haven 33881 $199,900 · 2 bd · 1 ba · 1,274 sqft
- 136 lake mariam road southeast, Winter Haven 33884 $385,000 · 4 bd · 3 ba · 2,356 sqft
- 3430 fox ridge street, Winter Haven 33884 $239,000 · 3 bd · 2 ba · 1,369 sqft
- 321 orange blossom drive, Winter Haven 33880 $199,950 · 2 bd · 3 ba · 1,407 sqft
- listing-10673520033, Winter Haven 33884 $270,000 · 3 bd · 2 ba · 1,470 sqft
- 86 parson drive, Winter Haven 33884 $103,000 · 2 bd · 2 ba · 1,260 sqft
- 1705 sandalwood circle southwest, Winter Haven 33880 $289,900 · 3 bd · 2 ba · 1,164 sqft
- 3462 avenue t northwest, Winter Haven 33881 $220,000 · 3 bd · 1 ba · 1,339 sqft
- 95 parson drive, Winter Haven 33884 $75,000 · 3 bd · 2 ba · 1,176 sqft
- 258 terranova boulevard, Winter Haven 33880 $409,000 · 4 bd · 3 ba · 2,639 sqft
- 213 lakeside ranch circle, Winter Haven 33881 $54,900 · 2 bd · 1 ba · 672 sqft
- 150 el dorado #105, Winter Haven 33884 $94,900 · 2 bd · 2 ba · 1,372 sqft
- listing-10673523063, Winter Haven 33881 $265,000 · 2 bd · 1 ba · 2,142 sqft
- 6703 canterbury drive northeast, Winter Haven 33881 $158,500 · 2 bd · 2 ba · 1,404 sqft
- 132 alachua drive, Winter Haven 33884 $310,000 · 3 bd · 2 ba · 2,466 sqft
- 1774 white elephant loop, Winter Haven 33884 $370,900 · 5 bd · 3 ba · 2,336 sqft
- 6044 grand oaks drive southeast, Winter Haven 33884 $145,000 · 2 bd · 2 ba · 1,248 sqft
- 381 san jose drive, Winter Haven 33884 $229,900 · 3 bd · 2 ba · 1,651 sqft
- 400 el camino drive #210, Winter Haven 33884 $96,000 · 3 bd · 3 ba · 1,666 sqft
- 981 lunar lane, Winter Haven 33884 $335,924 · 4 bd · 2 ba · 1,919 sqft
- 5118 kinsley drive, Winter Haven 33884 $389,999 · 5 bd · 4 ba · 3,030 sqft
- 1700 6th street northwest #c24, Winter Haven 33881 $92,000 · 2 bd · 1 ba · 840 sqft
- 1620 17th street northwest, Winter Haven 33881 $449,000 · 2 bd · 3 ba · 965 sqft
- 1919 19th street northwest, Winter Haven 33881 $349,000 · 4 bd · 2 ba · 1,752 sqft
- 2270 firestone place, Winter Haven 33884 $180,000 · 2 bd · 2 ba · 1,439 sqft
- 111 krenson bay loop, Winter Haven 33881 $280,000 · 3 bd · 2 ba · 1,543 sqft
- 1042 corso drive, Winter Haven 33884 $275,000 · 3 bd · 2 ba · 1,730 sqft
- 509 sharon hill court, Winter Haven 33880 $229,900 · 3 bd · 2 ba · 1,728 sqft
- 339 lake smart circle, Winter Haven 33881 $324,900 · 3 bd · 3 ba · 2,173 sqft