Homes under $500K in Winter Haven, FL

739 homes for sale · Updated August 13, 2026 · Page 11 of 15

• 1144 high seas street, Winter Haven 33880 $289,900 · 3 bd · 2 ba · 1,716 sqft
• 3319 avenue u northwest, Winter Haven 33881 $150,000 · 2 bd · 1 ba · 840 sqft
• 5437 san pietro drive, Winter Haven 33884 $364,999 · 5 bd · 3 ba · 2,470 sqft
• 5445 san pietro drive, Winter Haven 33884 $329,999 · 4 bd · 3 ba · 2,039 sqft
• 415 8th street northeast, Winter Haven 33881 $275,000 · 3 bd · 2 ba · 1,652 sqft
• 1097 normandy heights circle, Winter Haven 33880 $355,000 · 4 bd · 2 ba · 2,307 sqft
• 3420 avenue r northwest, Winter Haven 33881 $205,000 · 2 bd · 1 ba · 672 sqft
• 1814 sandhill lane, Winter Haven 33884 $482,000 · 4 bd · 3 ba · 2,550 sqft
• 715 avenue b southwest, Winter Haven 33880 $249,000 · 3 bd · 2 ba · 1,580 sqft
• 1365 sheridan street southwest, Winter Haven 33880 $232,000 · 2 bd · 1 ba · 1,199 sqft
• 1328 3rd street northeast, Winter Haven 33881 $215,000 · 3 bd · 2 ba · 1,118 sqft
• 6235 knotty pine drive southeast, Winter Haven 33884 $159,900 · 2 bd · 2 ba · 1,080 sqft
• 5449 san pietro drive, Winter Haven 33884 $329,999 · 4 bd · 3 ba · 2,039 sqft
• 5394 san pietro drive, Winter Haven 33884 $324,999 · 4 bd · 3 ba · 2,039 sqft
• 1 enclave drive, Winter Haven 33884 $225,000 · 3 bd · 2 ba · 1,676 sqft
• 1826 6th street southeast, Winter Haven 33880 $400,000 · 4 bd · 3 ba · 2,112 sqft
• 428 mckenna drive, Winter Haven 33881 $270,000 · 4 bd · 2 ba · 1,840 sqft
• 132 lake mariam way, Winter Haven 33884 $300,000 · 4 bd · 2 ba · 2,207 sqft
• 5148 magnolia preserve boulevard, Winter Haven 33880 $318,000 · 4 bd · 2 ba · 1,654 sqft
• 626 pavare court, Winter Haven 33884 $139,900 · 2 bd · 2 ba · 851 sqft
• 4925 jackson street, Winter Haven 33884 $279,900 · 3 bd · 2 ba · 1,425 sqft
• 372 lake daisy circle, Winter Haven 33884 $310,000 · 4 bd · 2 ba · 1,907 sqft
• 233 kensington view boulevard, Winter Haven 33880 $270,000 · 3 bd · 2 ba · 1,491 sqft
• 110 morning glory circle, Winter Haven 33884 $265,000 · 3 bd · 3 ba · 1,685 sqft
• 308 vaniman avenue, Winter Haven 33880 $229,900 · 3 bd · 2 ba · 1,228 sqft
• 934 cattleman street, Winter Haven 33884 $350,000 · 5 bd · 3 ba · 2,215 sqft
• 5811 marsh landing drive, Winter Haven 33881 $274,000 · 3 bd · 2 ba · 1,873 sqft
• 728 canberra road, Winter Haven 33884 $330,000 · 3 bd · 2 ba · 2,253 sqft
• 6249 botticella boulevard, Winter Haven 33884 $303,990 · 5 bd · 3 ba · 2,326 sqft
• 931 summer glen drive, Winter Haven 33880 $250,000 · 3 bd · 2 ba · 1,851 sqft
• 7902 waterview way, Winter Haven 33884 $189,900 · 2 bd · 2 ba · 930 sqft
• 307 avenue x northeast, Winter Haven 33881 $185,000 · 3 bd · 2 ba · 1,200 sqft
• 6280 botticella boulevard, Winter Haven 33884 $289,990 · 5 bd · 3 ba · 2,112 sqft
• 3334 white indigo road, Winter Haven 33884 $288,900 · 3 bd · 2 ba · 1,504 sqft
• 1753 hummingbird road, Winter Haven 33884 $425,585 · 5 bd · 3 ba · 2,490 sqft
• 6666 briarhill drive northeast, Winter Haven 33881 $140,000 · 2 bd · 2 ba · 1,144 sqft
• 5576 taverna loop, Winter Haven 33884 $283,990 · 3 bd · 2 ba · 1,504 sqft
• 1802 white elephant loop, Winter Haven 33884 $314,900 · 4 bd · 2 ba · 1,863 sqft
• 1628 hummingbird road, Winter Haven 33884 $284,900 · 3 bd · 2 ba · 1,593 sqft
• 333 lake howard drive northwest 211b, Winter Haven 33880 $149,900 · 3 bd · 2 ba · 1,218 sqft
• 444 avenue b northeast, Winter Haven 33881 $210,000 · 4 bd · 2 ba · 1,464 sqft
• 1404 axel circle, Winter Haven 33880 $365,000 · 5 bd · 3 ba · 2,523 sqft
• 2741 gladiola road, Winter Haven 33884 $273,990 · 3 bd · 3 ba · 1,758 sqft
• 2771 gladiola road, Winter Haven 33884 $273,990 · 3 bd · 3 ba · 1,758 sqft
• 2390 29th street northwest, Winter Haven 33881 $226,700 · 4 bd · 2 ba · 1,048 sqft
• 41 greenfield court, Winter Haven 33884 $370,000 · 3 bd · 2 ba · 2,054 sqft
• 3856 giorgio drive, Winter Haven 33884 $260,000 · 3 bd · 2 ba · 1,288 sqft
• 709 sarner pass way, Winter Haven 33881 $310,000 · 4 bd · 3 ba · 3,016 sqft
• 516 reggie road, Winter Haven 33884 $315,000 · 4 bd · 3 ba · 2,109 sqft
• 1776 6th street northwest 807, Winter Haven 33881 $162,000 · 2 bd · 2 ba · 1,347 sqft