Homes under $400K in Winter Haven, FL

505 for sale · 1,665 homes listed · Updated September 27, 2026 · Page 15 of 34

• 1640 northwest pearce road, Winter Haven 33881 Active Under Contract $330,000 · 3 bd · 2 ba · 1,421 sqft
• 1109 5th street southwest, Winter Haven 33880 Active Under Contract $195,000 · 3 bd · 2 ba · 1,238 sqft
• 880 oleander drive southeast, Winter Haven 33880 Active Under Contract $289,000 · 3 bd · 2 ba · 2,172 sqft
• 4127 sprucewood street, Winter Haven 33880 Active Under Contract $85,000 · 2 bd · 2 ba · 1,035 sqft
• 3228 country walk club circle, Winter Haven 33881 Active Under Contract $349,700 · 5 bd · 3 ba · 2,616 sqft
• 6346 bayberry boulevard northeast, Winter Haven 33881 Active Under Contract $189,900 · 3 bd · 2 ba · 1,440 sqft
• 731 canberra road, Winter Haven 33884 Active Under Contract $325,000 · 3 bd · 2 ba · 2,140 sqft
• 1150 high seas street, Winter Haven 33880 Active Under Contract $270,600 · 3 bd · 2 ba · 1,702 sqft
• 871 reflections loop east, Winter Haven 33884 Active Under Contract $213,000 · 3 bd · 2 ba · 1,264 sqft
• 2202 garden lake drive, Winter Haven 33884 Active Under Contract $249,000 · 3 bd · 2 ba · 1,442 sqft
• 6644 princeton drive northeast, Winter Haven 33881 Active Under Contract $129,900 · 2 bd · 2 ba · 1,296 sqft
• 1108 brenton manor drive, Winter Haven 33881 Active Under Contract $285,000 · 3 bd · 2 ba · 1,584 sqft
• 414 avenue c avenue northeast, Winter Haven 33881 Active Under Contract $214,999 · 2 bd · 2 ba · 1,140 sqft
• 345 24th street northwest 25, Winter Haven 33880 Active Under Contract $120,000 · 2 bd · 2 ba · 1,008 sqft
• 250 volusia drive, Winter Haven 33884 Active Under Contract $259,000 · 3 bd · 2 ba · 1,449 sqft
• 113 citrus drive, Winter Haven 33884 Active Under Contract $259,000 · 3 bd · 2 ba · 2,016 sqft
• 6518 crescent loop, Winter Haven 33884 Active Under Contract $230,000 · 3 bd · 2 ba · 1,894 sqft
• 4410 limewood street, Winter Haven 33880 Active Under Contract $110,000 · 2 bd · 2 ba · 1,152 sqft
• 3363 livingston way, Winter Haven 33884 Active Under Contract $235,000 · 2 bd · 2 ba · 1,118 sqft
• 345 24th street northwest 23, Winter Haven 33880 Active Under Contract $170,000 · 2 bd · 2 ba · 942 sqft
• 120 4th wahneta street east, Winter Haven 33880 Active Under Contract $150,000 · 3 bd · 2 ba · 864 sqft
• 1063 brimstone circle, Winter Haven 33884 Active Under Contract $336,000 · 4 bd · 3 ba · 2,476 sqft
• 1374 benevento drive, Winter Haven 33884 Active Under Contract $199,900 · 4 bd · 2 ba · 1,849 sqft
• 404 country lane northeast 404, Winter Haven 33881 Active Under Contract $80,000 · 2 bd · 2 ba · 1,252 sqft
• 3098 laurel oak lane, Winter Haven 33884 Active Under Contract $185,000 · 3 bd · 2 ba · 1,978 sqft
• 104 11th street southeast, Winter Haven 33880 Active Under Contract $267,500 · 3 bd · 3 ba · 1,792 sqft
• 6561 chinaberry drive northeast, Winter Haven 33881 Active Under Contract $155,900 · 2 bd · 2 ba · 1,596 sqft
• 15 lake howard drive northwest, Winter Haven 33880 Active Under Contract $240,000 · 6 bd · 4 ba · 2,883 sqft
• 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
• 2783 san marco way, Winter Haven 33884 Active Under Contract $312,990 · 4 bd · 3 ba · 2,298 sqft
• 2775 san marco way, Winter Haven 33884 Active Under Contract $319,990 · 4 bd · 3 ba · 2,298 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
• 116 mandolin drive, Winter Haven 33884 Active Under Contract $349,900 · 4 bd · 2 ba · 2,248 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