Homes under $300K in Winter Haven, FL

333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 11 of 23

• 303 dillon street, Winter Haven 33880 Active Under Contract $275,000 · 3 bd · 2 ba · 1,464 sqft
• 1646 tressel court, Winter Haven 33881 Active Under Contract $275,000 · 4 bd · 2 ba · 1,846 sqft
• 4717 magnolia preserve avenue, Winter Haven 33880 Active Under Contract $289,900 · 3 bd · 2 ba · 1,874 sqft
• 305 arbuthnot street, Winter Haven 33881 Active Under Contract $280,000 · 3 bd · 2 ba · 1,758 sqft
• 3027 richmond drive, Winter Haven 33884 Active Under Contract $279,000 · 3 bd · 2 ba · 1,994 sqft
• 6004 kaley drive, Winter Haven 33880 Active Under Contract $274,990 · 4 bd · 2 ba · 2,128 sqft
• 3147 whispering trails street, Winter Haven 33884 Active Under Contract $235,000 · 3 bd · 2 ba · 1,303 sqft
• 554 eagle landing boulevard, Winter Haven 33880 Active Under Contract $265,000 · 4 bd · 2 ba · 1,628 sqft
• 316 lake smart circle, Winter Haven 33881 Active Under Contract $264,900 · 3 bd · 2 ba · 1,500 sqft
• 1665 teagan lane, Winter Haven 33884 Active Under Contract $210,000 · 3 bd · 1 ba · 1,060 sqft
• 2826 avenue q northwest, Winter Haven 33881 Active Under Contract $207,990 · 3 bd · 1 ba · 840 sqft
• 3006 elm street, Winter Haven 33881 Active Under Contract $195,000 · 3 bd · 2 ba · 1,172 sqft
• 3642 queens cove boulevard, Winter Haven 33880 Active Under Contract $229,000 · 3 bd · 2 ba · 1,396 sqft
• 341 avenue l northeast, Winter Haven 33881 Active Under Contract $170,000 · 3 bd · 1 ba · 1,188 sqft
• 4880 old lucerne park road, Winter Haven 33881 Active Under Contract $119,000 · 2 bd · 1 ba · 660 sqft
• 505 holt circle, Winter Haven 33880 Active Under Contract $185,000 · 4 bd · 2 ba · 1,304 sqft
• 333 lake howard drive northwest 304b, Winter Haven 33880 Active Under Contract $80,000 · 3 bd · 2 ba · 1,330 sqft
• 124 6th wahneta street west, Winter Haven 33880 Active Under Contract $92,000 · 3 bd · 2 ba · 868 sqft
• 3311 queens cove loop, Winter Haven 33880 Active Under Contract $239,999 · 3 bd · 2 ba · 1,109 sqft
• 333 lake howard drive northwest 302d, Winter Haven 33880 Active Under Contract $89,900 · 2 bd · 2 ba · 1,030 sqft
• 352 vail drive, Winter Haven 33884 Active Under Contract $260,000 · 3 bd · 2 ba · 2,040 sqft
• 3421 hickory street northwest, Winter Haven 33881 Active Under Contract $182,000 · 2 bd · 1 ba · 690 sqft
• 3821 avenue j northwest, Winter Haven 33881 Active Under Contract $203,900 · 3 bd · 2 ba · 1,252 sqft
• 3136 country club circle, Winter Haven 33881 Active Under Contract $280,000 · 3 bd · 2 ba · 1,690 sqft
• 1676 teagan lane, Winter Haven 33884 Active Under Contract $299,000 · 4 bd · 3 ba · 2,093 sqft
• 2600 lucerne park road 521, Winter Haven 33881 Active Under Contract $159,000 · 2 bd · 2 ba · 845 sqft
• 2710 avenue j northwest, Winter Haven 33881 Active Under Contract $149,000 · 2 bd · 1 ba · 672 sqft
• 542 lake dexter boulevard, Winter Haven 33884 Active Under Contract $220,000 · 3 bd · 2 ba · 1,131 sqft
• 1100 martinique drive 105, Winter Haven 33884 Active Under Contract $50,000 · 1 bd · 1 ba · 663 sqft
• 321 squires grove drive, Winter Haven 33880 Active Under Contract $229,900 · 3 bd · 2 ba · 1,616 sqft
• 435 village circle southwest, Winter Haven 33880 Active Under Contract $137,500 · 2 bd · 2 ba · 1,120 sqft
• 1109 brimstone circle, Winter Haven 33884 Active Under Contract $264,000 · 3 bd · 2 ba · 1,697 sqft
• 2456 bates avenue southwest, Winter Haven 33881 Active Under Contract $249,900 · 3 bd · 2 ba · 1,232 sqft
• 608 patrick avenue, Winter Haven 33880 Active Under Contract $204,000 · 2 bd · 1 ba · 980 sqft
• 1912 carnostie road, Winter Haven 33884 Active Under Contract $245,000 · 3 bd · 2 ba · 1,464 sqft
• 2075 isle royale court southeast 171, Winter Haven 33880 Active Under Contract $77,000 · 1 bd · 1 ba · 648 sqft
• 2634 rutledge court, Winter Haven 33884 Active Under Contract $240,000 · 2 bd · 2 ba · 1,536 sqft
• 312 donald lane, Winter Haven 33880 Active Under Contract $190,000 · 2 bd · 2 ba · 840 sqft
• 905 avenue east northeast, Winter Haven 33881 Active Under Contract $199,995 · 2 bd · 1 ba · 912 sqft
• 110 valencia street, Winter Haven 33880 Active Under Contract $134,500 · 3 bd · 1 ba · 1,210 sqft
• 410 avenue a wahneta east, Winter Haven 33880 Active Under Contract $154,900 · 3 bd · 2 ba · 1,040 sqft
• 3962 cypress landing west, Winter Haven 33884 Active Under Contract $269,900 · 2 bd · 3 ba · 1,775 sqft
• 1966 white hawk way, Winter Haven 33881 Active Under Contract $285,000 · 4 bd · 2 ba · 1,862 sqft
• 2227 12th street northwest, Winter Haven 33881 Active Under Contract $285,000 · 3 bd · 2 ba · 1,773 sqft
• 4622 cypress gardens road, Winter Haven 33884 Active Under Contract $254,900 · 3 bd · 2 ba · 1,706 sqft
• 1496 33rd street northwest, Winter Haven 33881 Active Under Contract $94,900 · 2 bd · 1 ba · 720 sqft
• 406 saint anns drive, Winter Haven 33884 Active Under Contract $225,000 · 3 bd · 2 ba · 1,252 sqft
• 232 lake lucerne way, Winter Haven 33881 Active Under Contract $275,000 · 3 bd · 2 ba · 1,965 sqft
• 200 el camino drive 111, Winter Haven 33884 Active Under Contract $125,000 · 2 bd · 2 ba · 1,378 sqft
• 132 longfellow road, Winter Haven 33884 Active Under Contract $175,000 · 3 bd · 2 ba · 1,341 sqft