Homes under $500K in Winter Haven, FL

540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 29 of 36

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
1061 sawgrass drive, Winter Haven 33884 Off market since Sep 2026 $449,900 · 3 bd · 2 ba · 2,069 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
1814 sandhill lane, Winter Haven 33884 Off market since Sep 2026 $462,000 · 4 bd · 3 ba · 2,550 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
1826 6th street southeast, Winter Haven 33880 Off market since Sep 2026 $400,000 · 4 bd · 3 ba · 2,112 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
7902 waterview way, Winter Haven 33884 Off market since Sep 2026 $189,900 · 2 bd · 2 ba · 930 sqft
307 avenue x northeast, Winter Haven 33881 Off market since Sep 2026 $185,000 · 3 bd · 2 ba · 1,200 sqft
1753 hummingbird road, Winter Haven 33884 Off market since Sep 2026 $438,900 · 5 bd · 3 ba · 2,490 sqft
6666 briarhill drive northeast, Winter Haven 33881 Off market since Sep 2026 $140,000 · 2 bd · 2 ba · 1,144 sqft
1802 white elephant loop, Winter Haven 33884 Off market since Sep 2026 $314,900 · 4 bd · 2 ba · 1,863 sqft
1628 hummingbird road, Winter Haven 33884 Sold on Aug 14, 2026 $284,900 · 3 bd · 2 ba · 1,593 sqft
333 lake howard drive northwest 211b, Winter Haven 33880 Off market since Sep 2026 $149,900 · 3 bd · 2 ba · 1,218 sqft
444 avenue b northeast, Winter Haven 33881 Off market since Sep 2026 $179,000 · 4 bd · 2 ba · 1,464 sqft
1404 axel circle, Winter Haven 33880 Off market since Sep 2026 $365,000 · 5 bd · 3 ba · 2,523 sqft