Homes under $500K in Winter Haven, FL
540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 9 of 36
- 2122 lake boulevard, Winter Haven 33881 $248,000 · 3 bd · 1 ba · 985 sqft
- 1404 axel circle, Winter Haven 33880 $365,000 · 5 bd · 3 ba · 2,523 sqft
- 107 lake elizabeth drive #b, Winter Haven 33884 $119,000 · 1 bd · 1 ba · 625 sqft
- 2307 scarlet avenue, Winter Haven 33884 $260,000 · 3 bd · 2 ba · 1,343 sqft
- 205 tifton street, Winter Haven 33880 $399,999 · 5 bd · 4 ba · 3,040 sqft
- 1122 brimstone circle, Winter Haven 33884 $325,000 · 3 bd · 2 ba · 1,690 sqft
- 100 el camino drive #111, Winter Haven 33884 $65,000 · 1 bd · 1 ba · 931 sqft
- 1382 salisbury drive, Winter Haven 33881 $293,899 · 4 bd · 3 ba · 1,764 sqft
- 1550 11th street northeast #g6, Winter Haven 33881 $139,000 · 2 bd · 2 ba · 1,148 sqft
- 6458 hollyberry lane northeast, Winter Haven 33881 $179,000 · 2 bd · 2 ba · 1,248 sqft
- 5445 chandler drive, Winter Haven 33884 $290,000 · 4 bd · 3 ba · 3,010 sqft
- 6627 westchester drive northeast, Winter Haven 33881 $198,000 · 2 bd · 2 ba · 1,856 sqft
- 6455 hollyberry lane northeast, Winter Haven 33881 $152,000 · 2 bd · 2 ba · 1,144 sqft
- 704 eagle pond drive #704, Winter Haven 33884 $169,900 · 2 bd · 2 ba · 1,017 sqft
- 1116 40th street northwest, Winter Haven 33881 $44,900 · 3 bd · 2 ba · 988 sqft
- 199 8th street southeast, Winter Haven 33880 $405,000 · 5 bd · 2 ba · 2,992 sqft
- 6309 grove pointe drive southeast, Winter Haven 33884 $154,000 · 2 bd · 2 ba · 1,248 sqft
- 2021 oliver place, Winter Haven 33881 $274,990 · 3 bd · 2 ba · 1,507 sqft
- 4519 rapallo avenue, Winter Haven 33884 $329,900 · 4 bd · 3 ba · 2,074 sqft
- 444 avenue b northeast, Winter Haven 33881 $179,000 · 4 bd · 2 ba · 1,464 sqft
- 183 lake thomas, Winter Haven 33880 $450,000 · 4 bd · 2 ba · 2,385 sqft
- 128 11th wahneta street west, Winter Haven 33880 $214,500 · 3 bd · 1 ba · 1,008 sqft
- 5621 forest ridge drive, Winter Haven 33881 $249,900 · 3 bd · 2 ba · 1,256 sqft
- 2118 edgewater circle, Winter Haven 33880 $369,000 · 4 bd · 3 ba · 2,763 sqft
- 1004 medinah drive, Winter Haven 33884 $165,000 · 2 bd · 2 ba · 1,278 sqft
- 301 terranova boulevard, Winter Haven 33884 $379,900 · 4 bd · 2 ba · 1,960 sqft
- 321 alexzander way, Winter Haven 33881 $339,900 · 5 bd · 3 ba · 2,696 sqft
- 5394 san pietro drive, Winter Haven 33884 $312,999 · 4 bd · 3 ba · 2,039 sqft
- 5390 san pietro drive, Winter Haven 33884 $384,999 · 5 bd · 3 ba · 3,016 sqft
- 507 short lane, Winter Haven 33881 $339,000 · 4 bd · 2 ba · 1,867 sqft
- 1864 emily drive, Winter Haven 33884 $287,500 · 4 bd · 2 ba · 1,836 sqft
- 1716 terry circle northeast, Winter Haven 33881 $270,000 · 3 bd · 2 ba · 1,065 sqft
- 271 inman boulevard, Winter Haven 33881 $340,000 · 5 bd · 3 ba · 2,274 sqft
- 937 cattleman street, Winter Haven 33881 $340,000 · 4 bd · 2 ba · 1,828 sqft
- 4629 palmetto drive, Winter Haven 33881 $320,000 · 3 bd · 2 ba · 1,558 sqft
- 7060 fairview village circle, Winter Haven 33881 $134,990 · 1 bd · 1 ba · 481 sqft
- 9705 lake bess road #715, Winter Haven 33884 $119,000 · 2 bd · 2 ba · 792 sqft
- 477 kensington view drive, Winter Haven 33880 $300,000 · 3 bd · 2 ba · 1,750 sqft
- 3344 timberline road west, Winter Haven 33880 $229,000 · 2 bd · 2 ba · 904 sqft
- 345 avenue p northeast, Winter Haven 33881 $189,000 · 3 bd · 1 ba · 744 sqft
- 24 flamingo boulevard, Winter Haven 33880 $229,900 · 3 bd · 2 ba · 1,344 sqft
- 5441 san pietro drive, Winter Haven 33884 $364,999 · 5 bd · 3 ba · 2,470 sqft
- 464 terranova street, Winter Haven 33884 $359,900 · 3 bd · 2 ba · 1,893 sqft
- 4669 osprey way, Winter Haven 33881 $309,000 · 4 bd · 2 ba · 1,992 sqft
- 1550 36th street northwest, Winter Haven 33881 $174,900 · 3 bd · 1 ba · 1,226 sqft
- 1742 upland lane, Winter Haven 33884 $392,175 · 4 bd · 3 ba · 2,551 sqft
- 1726 upland lane, Winter Haven 33884 $386,990 · 4 bd · 3 ba · 2,797 sqft
- 2252 labrador loop, Winter Haven 33884 $341,565 · 3 bd · 2 ba · 1,815 sqft
- 2240 labrador loop, Winter Haven 33884 $323,965 · 3 bd · 2 ba · 1,549 sqft
- 2236 labrador loop, Winter Haven 33884 $350,165 · 4 bd · 2 ba · 2,021 sqft