Homes under $300K in Winter Haven, FL
333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 6 of 23
- 2796 whispering trails drive, Winter Haven 33884 $190,000 · 3 bd · 2 ba · 1,158 sqft
- 683 broadmoor circle #683, Winter Haven 33884 $193,000 · 2 bd · 2 ba · 1,139 sqft
- 664 clubhouse road, Winter Haven 33884 $229,000 · 2 bd · 2 ba · 1,395 sqft
- 10 enclave drive, Winter Haven 33884 $214,900 · 2 bd · 2 ba · 1,368 sqft
- 2436 edwin street northeast, Winter Haven 33881 $218,994 · 4 bd · 2 ba · 1,813 sqft
- 1268 salisbury drive, Winter Haven 33881 $255,000 · 3 bd · 2 ba · 1,728 sqft
- 6666 briarhill drive northeast, Winter Haven 33881 $140,000 · 2 bd · 2 ba · 1,144 sqft
- 125 edgewater drive, Winter Haven 33881 $210,000 · 4 bd · 3 ba · 1,703 sqft
- 940 oleander drive southeast, Winter Haven 33880 $250,000 · 2 bd · 2 ba · 1,527 sqft
- 3268 country walk club circle, Winter Haven 33881 $295,000 · 3 bd · 2 ba · 1,690 sqft
- 563 honey bell road, Winter Haven 33880 $299,900 · 4 bd · 2 ba · 1,851 sqft
- 1701 36th street northwest, Winter Haven 33881 $257,999 · 4 bd · 2 ba · 1,815 sqft
- 2122 lake boulevard, Winter Haven 33881 $248,000 · 3 bd · 1 ba · 985 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
- 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
- 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
- 444 avenue b northeast, Winter Haven 33881 $179,000 · 4 bd · 2 ba · 1,464 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
- 1004 medinah drive, Winter Haven 33884 $165,000 · 2 bd · 2 ba · 1,278 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
- 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
- 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
- 1550 36th street northwest, Winter Haven 33881 $174,900 · 3 bd · 1 ba · 1,226 sqft
- 1220 33rd street northwest, Winter Haven 33881 $150,000 · 3 bd · 1 ba · 1,141 sqft
- 146 8th street, Winter Haven 33880 $250,000 · 3 bd · 2 ba · 1,404 sqft
- 622 crystals boulevard, Winter Haven 33884 $229,500 · 3 bd · 2 ba · 1,328 sqft
- 428 mckenna drive, Winter Haven 33881 $260,000 · 4 bd · 2 ba · 1,840 sqft
- 2500 21st street northwest #15, Winter Haven 33881 $168,000 · 2 bd · 3 ba · 1,184 sqft
- 310 ogden street, Winter Haven 33880 $185,000 · 3 bd · 2 ba · 1,151 sqft
- 4140 sophia boulevard, Winter Haven 33880 $255,000 · 3 bd · 2 ba · 1,711 sqft
- 709 sarner pass way, Winter Haven 33881 $279,900 · 4 bd · 3 ba · 3,016 sqft
- 333 lake howard drive northwest #314d, Winter Haven 33880 $99,000 · 3 bd · 2 ba · 1,226 sqft
- 297 meadowbrook boulevard, Winter Haven 33881 $230,000 · 3 bd · 2 ba · 1,426 sqft
- 256 krenson bay loop, Winter Haven 33881 $290,000 · 3 bd · 2 ba · 1,720 sqft
- 1714 carnostie road, Winter Haven 33884 $285,000 · 3 bd · 2 ba · 1,515 sqft