Homes under $1M in Winter Haven, FL

572 for sale · 1,886 homes listed · Updated September 27, 2026 · Page 18 of 38

• 840 piedmont drive southeast, Winter Haven 33880 Active Under Contract $425,000 · 3 bd · 2 ba · 1,870 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
• 4000 oak preserve drive, Winter Haven 33880 Active Under Contract $309,900 · 3 bd · 2 ba · 1,901 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
• 1210 west lake hamilton drive, Winter Haven 33881 Active Under Contract $615,000 · 4 bd · 2 ba · 2,701 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
• 1549 drexel avenue northeast, Winter Haven 33881 Active Under Contract $400,000 · 2 bd · 2 ba · 1,120 sqft
• 2075 isle royale court southeast 171, Winter Haven 33880 Active Under Contract $77,000 · 1 bd · 1 ba · 648 sqft
• 3312 queens cove loop, Winter Haven 33880 Active Under Contract $307,900 · 3 bd · 2 ba · 1,109 sqft
• 2634 rutledge court, Winter Haven 33884 Active Under Contract $240,000 · 2 bd · 2 ba · 1,536 sqft
• 2925 east lake hartridge drive, Winter Haven 33881 Active Under Contract $399,000 · 4 bd · 3 ba · 2,684 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
• 440 palma ceia road, Winter Haven 33884 Active Under Contract $750,000 · 4 bd · 3 ba · 2,575 sqft
• 2227 12th street northwest, Winter Haven 33881 Active Under Contract $285,000 · 3 bd · 2 ba · 1,773 sqft
• 419 pinellas road, Winter Haven 33884 Active Under Contract $399,999 · 4 bd · 3 ba · 2,248 sqft
• 3749 fieldstone circle, Winter Haven 33881 Active Under Contract $459,990 · 5 bd · 3 ba · 2,588 sqft
• 302 sterling drive, Winter Haven 33884 Active Under Contract $315,000 · 4 bd · 2 ba · 2,460 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
• 6549 crescent loop, Winter Haven 33884 Active Under Contract $300,000 · 4 bd · 3 ba · 1,883 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
• 1144 high seas street, Winter Haven 33880 Active Under Contract $289,900 · 3 bd · 2 ba · 1,716 sqft
• 1097 normandy heights circle, Winter Haven 33880 Active Under Contract $349,900 · 4 bd · 2 ba · 2,307 sqft
• 814 carlton court, Winter Haven 33884 Active Under Contract $415,000 · 4 bd · 3 ba · 2,371 sqft
• 650 avenue north southeast, Winter Haven 33880 Active Under Contract $225,000 · 4 bd · 3 ba · 1,839 sqft
• 1040 cambridge drive, Winter Haven 33881 Active Under Contract $235,000 · 3 bd · 2 ba · 1,727 sqft
• 832 cambridge drive, Winter Haven 33881 Active Under Contract $336,900 · 4 bd · 3 ba · 1,980 sqft
• 505 glad road, Winter Haven 33880 Active Under Contract $239,900 · 3 bd · 2 ba · 1,270 sqft
• 4925 jackson street, Winter Haven 33884 Active Under Contract $249,900 · 3 bd · 2 ba · 1,425 sqft
• 2760 sunset drive northwest, Winter Haven 33881 Active Under Contract $300,000 · 3 bd · 2 ba · 1,514 sqft
• 120 morning glory circle, Winter Haven 33884 Active Under Contract $345,000 · 3 bd · 2 ba · 1,930 sqft
• 2771 gladiola road, Winter Haven 33884 Active Under Contract $273,990 · 3 bd · 3 ba · 1,758 sqft
• 207 winter ridge boulevard 4, Winter Haven 33881 Active Under Contract $145,000 · 2 bd · 2 ba · 1,073 sqft
• 524 haines trail, Winter Haven 33881 Active Under Contract $279,999 · 4 bd · 2 ba · 1,980 sqft