Homes under $400K in Winter Haven, FL

505 for sale · 1,665 homes listed · Updated September 27, 2026 · Page 24 of 34

1213 8th street northwest, Winter Haven 33881 Off market since Sep 2026 $189,000 · 2 bd · 2 ba · 972 sqft
884 cambridge drive, Winter Haven 33881 Off market since Sep 2026 $279,000 · 4 bd · 3 ba · 2,368 sqft
218 dennis avenue, Winter Haven 33880 Off market since Sep 2026 $246,900 · 3 bd · 1 ba · 1,174 sqft
138 whittier lane, Winter Haven 33884 Off market since Sep 2026 $319,000 · 4 bd · 3 ba · 1,665 sqft
1558 drexel avenue northeast, Winter Haven 33881 Off market since Sep 2026 $329,900 · 3 bd · 2 ba · 1,160 sqft
780 overlook grove drive, Winter Haven 33884 Off market since Sep 2026 $269,900 · 4 bd · 2 ba · 1,583 sqft
811 22nd street northwest, Winter Haven 33881 Off market since Sep 2026 $269,990 · 3 bd · 3 ba · 1,408 sqft
6103 grey heron drive, Winter Haven 33881 Off market since Sep 2026 $295,000 · 4 bd · 2 ba · 1,828 sqft
1210 zambrana court, Winter Haven 33884 Off market since Sep 2026 $339,000 · 4 bd · 2 ba · 2,360 sqft
5393 san pietro drive, Winter Haven 33884 Off market since Sep 2026 $384,999 · 5 bd · 3 ba · 3,016 sqft
524 haines trail, Winter Haven 33881 Off market since Jul 2026 $299,000 · 3 bd · 2 ba · 1,980 sqft
1633 nantucket way, Winter Haven 33884 Off market since Jul 2026 $338,900 · 4 bd · 2 ba · 1,863 sqft
136 lake ring drive, Winter Haven 33884 Off market since Sep 2026 $299,900 · 3 bd · 2 ba · 1,728 sqft
2108 river hawk loop, Winter Haven 33880 Off market since Sep 2026 $384,900 · 4 bd · 2 ba · 2,032 sqft
2330 southeast royal isle, Winter Haven 33880 Off market since Sep 2026 $215,000 · 2 bd · 3 ba · 1,312 sqft
4253 cedarwood street, Winter Haven 33880 Off market since Sep 2026 $99,000 · 2 bd · 2 ba · 1,056 sqft
3307 costello circle, Winter Haven 33884 Off market since Sep 2026 $289,000 · 3 bd · 2 ba · 1,553 sqft
3151 laurel oak lane, Winter Haven 33884 Off market since Sep 2026 $333,900 · 4 bd · 3 ba · 2,029 sqft
604 sarner pass way, Winter Haven 33881 Off market since Sep 2026 $340,000 · 4 bd · 2 ba · 2,004 sqft
339 lake smart circle, Winter Haven 33881 Off market since Sep 2026 $324,900 · 3 bd · 3 ba · 2,173 sqft
507 short lane, Winter Haven 33881 Off market since Sep 2026 $340,000 · 4 bd · 2 ba · 1,867 sqft
4856 summerfield circle, Winter Haven 33881 Off market since Jul 2026 $299,900 · 4 bd · 2 ba · 1,688 sqft
125 andreas street, Winter Haven 33881 Off market since Sep 2026 $300,000 · 4 bd · 2 ba · 1,823 sqft
1303 37th street northwest, Winter Haven 33881 Off market since Sep 2026 $215,000 · 3 bd · 2 ba · 640 sqft
1405 avenue h southwest, Winter Haven 33880 Off market since Aug 2026 $240,000 · 3 bd · 2 ba · 1,502 sqft
1782 white elephant, Winter Haven 33884 Off market since Sep 2026 $314,900 · 4 bd · 2 ba · 1,863 sqft
207 avenue east southeast, Winter Haven 33880 Off market since Aug 2026 $399,900 · 4 bd · 4 ba · 2,093 sqft
4212 cedarwood street, Winter Haven 33880 Off market since Sep 2026 $129,900 · 2 bd · 2 ba · 1,265 sqft
3023 caneel street, Winter Haven 33884 Off market since Sep 2026 $235,000 · 2 bd · 2 ba · 1,385 sqft
1660 hummingbird road, Winter Haven 33884 Off market since Sep 2026 $286,900 · 3 bd · 2 ba · 1,593 sqft
567 eagle landing boulevard, Winter Haven 33880 Off market since Sep 2026 $375,000 · 4 bd · 3 ba · 2,193 sqft
317 avenue g southeast, Winter Haven 33880 Off market since Sep 2026 $250,000 · 4 bd · 3 ba · 1,610 sqft
137 lowell road, Winter Haven 33884 Off market since Sep 2026 $272,000 · 3 bd · 2 ba · 1,435 sqft
5373 san pietro drive, Winter Haven 33884 Off market since Sep 2026 $364,999 · 5 bd · 3 ba · 2,471 sqft
5377 san pietro drive, Winter Haven 33884 Off market since Sep 2026 $309,999 · 4 bd · 3 ba · 2,039 sqft
3155 country club circle, Winter Haven 33881 Off market since Sep 2026 $310,000 · 4 bd · 2 ba · 1,851 sqft
1004 medinah drive, Winter Haven 33884 Off market since Sep 2026 $165,000 · 2 bd · 2 ba · 1,278 sqft
1100 carefree cove drive, Winter Haven 33881 Off market since Sep 2026 $200,000 · 3 bd · 2 ba · 1,019 sqft
404 lake ned road, Winter Haven 33884 Off market since Sep 2026 $259,000 · 3 bd · 2 ba · 1,439 sqft
3924 giorgio drive, Winter Haven 33884 Off market since Jul 2026 $274,100 · 3 bd · 2 ba · 1,483 sqft
3964 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $325,000 · 4 bd · 3 ba · 2,387 sqft
419 avenue m northeast, Winter Haven 33881 Off market since Sep 2026 $244,999 · 3 bd · 2 ba · 1,232 sqft
10 enclave drive, Winter Haven 33884 Off market since Sep 2026 $214,900 · 2 bd · 2 ba · 1,368 sqft
6194 grey heron drive, Winter Haven 33881 Off market since Sep 2026 $290,000 · 3 bd · 2 ba · 1,711 sqft
329 lake daisy loop, Winter Haven 33884 Off market since Sep 2026 $320,000 · 3 bd · 2 ba · 1,563 sqft
702 country lane northeast 702, Winter Haven 33881 Off market since Sep 2026 $169,500 · 2 bd · 2 ba · 1,252 sqft
1871 emily drive, Winter Haven 33884 Off market since Sep 2026 $304,900 · 4 bd · 2 ba · 2,012 sqft
1473 lucerne loop road northeast, Winter Haven 33881 Off market since Aug 2026 $260,000 · 4 bd · 2 ba · 1,599 sqft
4114 fishermans landing, Winter Haven 33884 Off market since Sep 2026 $295,000 · 3 bd · 2 ba · 1,992 sqft
2122 river hawk loop, Winter Haven 33880 Off market since Sep 2026 $344,900 · 4 bd · 2 ba · 1,741 sqft