Homes under $500K in Winter Haven, FL
540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 25 of 36
- 205 arbuthnot street, Winter Haven 33881 Off market since Jul 2026 $299,777 · 3 bd · 2 ba · 1,447 sqft
- 909 cambridge drive, Winter Haven 33881 Off market since Sep 2026 $256,900 · 3 bd · 2 ba · 1,506 sqft
- 1192 normandy heights circle, Winter Haven 33880 Off market since Sep 2026 $337,000 · 4 bd · 3 ba · 2,093 sqft
- 3971 cypress landing west, Winter Haven 33884 Off market since Sep 2026 $289,900 · 3 bd · 2 ba · 1,674 sqft
- 4669 osprey way, Winter Haven 33881 Off market since Sep 2026 $309,000 · 4 bd · 2 ba · 1,992 sqft
- 3890 bedford avenue, Winter Haven 33884 Off market since Sep 2026 $395,000 · 4 bd · 3 ba · 2,322 sqft
- 3060 captain jax way, Winter Haven 33884 Off market since Aug 2026 $239,990 · 3 bd · 3 ba · 1,423 sqft
- 323 orange blossom drive 323, Winter Haven 33880 Off market since Sep 2026 $205,000 · 2 bd · 3 ba · 1,280 sqft
- 2747 san marco way, Winter Haven 33884 Off market since Sep 2026 $284,990 · 3 bd · 2 ba · 1,680 sqft
- 3420 avenue t northwest, Winter Haven 33881 Off market since Sep 2026 $225,000 · 3 bd · 3 ba · 1,088 sqft
- 3732 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $250,000 · 4 bd · 2 ba · 1,713 sqft
- 1742 upland lane, Winter Haven 33884 Off market since Sep 2026 $392,175 · 4 bd · 3 ba · 2,551 sqft
- 1726 upland lane, Winter Haven 33884 Off market since Sep 2026 $386,990 · 4 bd · 3 ba · 2,797 sqft
- 306 palmetto avenue northwest, Winter Haven 33881 Off market since Sep 2026 $179,000 · 3 bd · 1 ba · 768 sqft
- 202 saint lucie road, Winter Haven 33884 Off market since Sep 2026 $299,900 · 3 bd · 2 ba · 1,764 sqft
- 445 mckenna drive, Winter Haven 33881 Off market since Sep 2026 $299,000 · 4 bd · 2 ba · 1,694 sqft
- 314 terranova boulevard, Winter Haven 33884 Off market since Sep 2026 $350,000 · 3 bd · 2 ba · 1,884 sqft
- 2130 34th street northwest, Winter Haven 33881 Sold on Jul 10, 2026 $135,000 · 3 bd · 1 ba · 1,068 sqft
- 4038 rolling oaks drive, Winter Haven 33880 Off market since Sep 2026 $74,900 · 2 bd · 2 ba · 1,056 sqft
- 6114 grand oaks drive southeast, Winter Haven 33884 Off market since Sep 2026 $159,900 · 2 bd · 2 ba · 1,288 sqft
- 825 northwest avenue y avenue northwest, Winter Haven 33881 Off market since Aug 2026 $285,000 · 3 bd · 1 ba · 1,497 sqft
- 300 avenue v northeast, Winter Haven 33881 Off market since Sep 2026 $165,000 · 3 bd · 1 ba · 912 sqft
- 128 avenue d southwest, Winter Haven 33880 Off market since Sep 2026 $175,000 · 5 bd · 2 ba · 2,200 sqft
- 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
- 100 alachua drive, Winter Haven 33884 Off market since Sep 2026 $499,900 · 3 bd · 2 ba · 2,002 sqft
- 1633 nantucket way, Winter Haven 33884 Off market since Jul 2026 $338,900 · 4 bd · 2 ba · 1,863 sqft
- 2112 river hawk loop, Winter Haven 33880 Off market since Sep 2026 $429,900 · 4 bd · 3 ba · 2,378 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
- 258 terranova boulevard, Winter Haven 33880 Off market since Sep 2026 $409,000 · 4 bd · 3 ba · 2,639 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