Homes under $400K in Winter Haven, FL

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

528 mckenna drive, Winter Haven 33881 Off market since Sep 2026 $330,000 · 4 bd · 3 ba · 1,964 sqft
306 terranova boulevard, Winter Haven 33884 Off market since Sep 2026 $370,000 · 4 bd · 3 ba · 2,413 sqft
3025 captain jax way, Winter Haven 33884 Off market since Sep 2026 $245,140 · 3 bd · 3 ba · 1,423 sqft
516 reggie road, Winter Haven 33884 Off market since Jul 2026 $325,000 · 4 bd · 3 ba · 2,109 sqft
4049 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $286,900 · 3 bd · 2 ba · 1,504 sqft
1700 6th street northwest c21, Winter Haven 33881 Off market since Sep 2026 $92,000 · 2 bd · 2 ba · 840 sqft
681 lake dexter circle, Winter Haven 33884 Off market since Jul 2026 $349,000 · 3 bd · 3 ba · 1,320 sqft
622 crystals boulevard, Winter Haven 33884 Off market since Sep 2026 $229,500 · 3 bd · 2 ba · 1,328 sqft
204 4th jpv street, Winter Haven 33880 Off market since Jul 2026 $175,000 · 3 bd · 2 ba · 1,068 sqft
3530 evening star drive, Winter Haven 33881 Off market since Sep 2026 $315,000 · 4 bd · 2 ba · 1,822 sqft
105 lake sears drive, Winter Haven 33880 Off market since Aug 2026 $279,900 · 3 bd · 2 ba · 1,513 sqft
1454 austin street, Winter Haven 33884 Off market since Sep 2026 $320,000 · 5 bd · 3 ba · 2,254 sqft
6604 winterset gardens road, Winter Haven 33884 Off market since Jul 2026 $250,000 · 3 bd · 3 ba · 2,459 sqft
129 florida drive, Winter Haven 33881 Off market since Jul 2026 $140,000 · 3 bd · 1 ba · 1,088 sqft
2711 gladiola road, Winter Haven 33884 Off market since Sep 2026 $254,900 · 3 bd · 3 ba · 1,673 sqft
1738 hummingbird road, Winter Haven 33884 Off market since Sep 2026 $316,900 · 4 bd · 2 ba · 1,720 sqft
3129 avenue west northwest, Winter Haven 33881 Off market since Sep 2026 $212,000 · 3 bd · 1 ba · 1,500 sqft
1525 oakview circle southeast, Winter Haven 33880 Off market since Sep 2026 $199,000 · 2 bd · 2 ba · 1,333 sqft
4242 cedarwood street, Winter Haven 33880 Off market since Sep 2026 $110,000 · 2 bd · 2 ba · 1,056 sqft
5308 green drive, Winter Haven 33884 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,495 sqft
321 alexzander way, Winter Haven 33881 Off market since Sep 2026 $339,900 · 5 bd · 3 ba · 2,696 sqft
6053 southern oaks drive southeast, Winter Haven 33884 Off market since Jul 2026 $136,900 · 2 bd · 2 ba · 1,104 sqft
1642 teagan lane, Winter Haven 33884 Off market since Sep 2026 $329,900 · 4 bd · 3 ba · 1,896 sqft
2216 starboard, Winter Haven 33881 Off market since Sep 2026 $215,000 · 3 bd · 3 ba · 1,549 sqft
2230 west central avenue, Winter Haven 33880 Off market since Sep 2026 $314,500 · 3 bd · 2 ba · 1,788 sqft
406 lake daisy drive, Winter Haven 33884 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,406 sqft
1405 28th street northwest, Winter Haven 33881 Off market since Sep 2026 $220,000 · 2 bd · 1 ba · 1,137 sqft
3319 avenue u northwest, Winter Haven 33881 Off market since Sep 2026 $145,000 · 2 bd · 1 ba · 840 sqft
5445 san pietro drive, Winter Haven 33884 Off market since Sep 2026 $319,999 · 4 bd · 3 ba · 2,039 sqft
211 golf aire boulevard, Winter Haven 33884 Sold on Jul 21, 2026 $299,900 · 3 bd · 2 ba · 1,650 sqft
415 8th street northeast, Winter Haven 33881 Off market since Sep 2026 $255,000 · 3 bd · 2 ba · 1,652 sqft
3420 avenue r northwest, Winter Haven 33881 Off market since Sep 2026 $205,000 · 2 bd · 1 ba · 672 sqft
715 avenue b southwest, Winter Haven 33880 Off market since Sep 2026 $239,900 · 3 bd · 2 ba · 1,580 sqft
2865 whispering trails drive, Winter Haven 33884 Off market since Sep 2026 $234,900 · 3 bd · 2 ba · 1,253 sqft
1365 sheridan street southwest, Winter Haven 33880 Off market since Sep 2026 $222,000 · 2 bd · 1 ba · 1,199 sqft
1328 3rd street northeast, Winter Haven 33881 Off market since Sep 2026 $199,999 · 3 bd · 2 ba · 1,118 sqft
6235 knotty pine drive southeast, Winter Haven 33884 Off market since Sep 2026 $155,000 · 2 bd · 2 ba · 1,080 sqft
5449 san pietro drive, Winter Haven 33884 Off market since Sep 2026 $309,999 · 4 bd · 3 ba · 2,039 sqft
5394 san pietro drive, Winter Haven 33884 Off market since Sep 2026 $312,999 · 4 bd · 3 ba · 2,039 sqft
1 enclave drive, Winter Haven 33884 Off market since Sep 2026 $220,000 · 3 bd · 2 ba · 1,676 sqft
428 mckenna drive, Winter Haven 33881 Off market since Sep 2026 $260,000 · 4 bd · 2 ba · 1,840 sqft
5148 magnolia preserve boulevard, Winter Haven 33880 Off market since Sep 2026 $318,000 · 4 bd · 2 ba · 1,654 sqft
626 pavare court, Winter Haven 33884 Off market since Sep 2026 $129,900 · 2 bd · 2 ba · 851 sqft
372 lake daisy circle, Winter Haven 33884 Off market since Sep 2026 $310,000 · 4 bd · 2 ba · 1,907 sqft
233 kensington view boulevard, Winter Haven 33880 Off market since Sep 2026 $270,000 · 3 bd · 2 ba · 1,491 sqft
110 morning glory circle, Winter Haven 33884 Off market since Sep 2026 $265,000 · 3 bd · 3 ba · 1,685 sqft
308 vaniman avenue, Winter Haven 33880 Off market since Sep 2026 $229,900 · 3 bd · 2 ba · 1,228 sqft
5811 marsh landing drive, Winter Haven 33881 Off market since Sep 2026 $269,000 · 3 bd · 2 ba · 1,873 sqft
728 canberra road, Winter Haven 33884 Off market since Aug 2026 $330,000 · 3 bd · 2 ba · 2,253 sqft
931 summer glen drive, Winter Haven 33880 Off market since Sep 2026 $225,000 · 3 bd · 2 ba · 1,851 sqft