Homes under $500K in Winter Haven, FL

739 homes for sale · Updated August 13, 2026 · Page 10 of 15

• 6272 botticella boulevard, Winter Haven 33884 $289,490 · 5 bd · 3 ba · 2,112 sqft
• 110 valencia street, Winter Haven 33880 $134,500 · 3 bd · 1 ba · 1,210 sqft
• 1620 17th street northwest, Winter Haven 33881 $469,000 · 2 bd · 3 ba · 965 sqft
• 2500 21st street northwest 22, Winter Haven 33881 $178,990 · 2 bd · 3 ba · 1,334 sqft
• 435 16th street northeast, Winter Haven 33881 $245,000 · 3 bd · 1 ba · 1,700 sqft
• 820 26th street northwest, Winter Haven 33881 $259,000 · 3 bd · 2 ba · 1,122 sqft
• 509 sharon hill court, Winter Haven 33880 $234,700 · 3 bd · 2 ba · 1,728 sqft
• 664 clubhouse road, Winter Haven 33884 $235,000 · 2 bd · 2 ba · 1,395 sqft
• 54 lake link circle southeast, Winter Haven 33884 $319,900 · 3 bd · 2 ba · 1,752 sqft
• 1966 white hawk way, Winter Haven 33881 $285,000 · 4 bd · 2 ba · 1,862 sqft
• 2452 salzburg loop, Winter Haven 33884 $300,000 · 2 bd · 2 ba · 1,729 sqft
• 136 lake mariam road southeast, Winter Haven 33884 $398,000 · 4 bd · 3 ba · 2,356 sqft
• 516 alachua drive, Winter Haven 33884 $369,000 · 3 bd · 2 ba · 1,699 sqft
• 4146 sprucewood street, Winter Haven 33880 $140,000 · 2 bd · 2 ba · 1,344 sqft
• 108 edgewater drive, Winter Haven 33881 $285,000 · 4 bd · 2 ba · 1,450 sqft
• 199 8th street southeast, Winter Haven 33880 $410,000 · 5 bd · 2 ba · 2,992 sqft
• 3614 plymouth drive, Winter Haven 33884 $310,000 · 3 bd · 2 ba · 2,109 sqft
• 2095 west hartridge terrace, Winter Haven 33881 $299,900 · 3 bd · 2 ba · 1,816 sqft
• 3749 fieldstone circle, Winter Haven 33881 $464,900 · 5 bd · 3 ba · 2,588 sqft
• 180 solis drive, Winter Haven 33880 $268,520 · 3 bd · 2 ba · 1,460 sqft
• 528 mckenna drive, Winter Haven 33881 $375,000 · 4 bd · 3 ba · 1,964 sqft
• 306 terranova boulevard, Winter Haven 33884 $375,000 · 4 bd · 3 ba · 2,413 sqft
• 3025 captain jax way, Winter Haven 33884 $239,990 · 3 bd · 3 ba · 1,423 sqft
• 4045 giorgio drive, Winter Haven 33884 $299,990 · 4 bd · 2 ba · 1,665 sqft
• 4049 giorgio drive, Winter Haven 33884 $286,990 · 3 bd · 2 ba · 1,504 sqft
• 4079 lake marianna drive, Winter Haven 33881 $184,900 · 3 bd · 2 ba · 1,054 sqft
• 1700 6th street northwest c21, Winter Haven 33881 $92,000 · 2 bd · 2 ba · 840 sqft
• 622 crystals boulevard, Winter Haven 33884 $239,900 · 3 bd · 2 ba · 1,328 sqft
• 302 sterling drive, Winter Haven 33884 $350,000 · 4 bd · 2 ba · 2,460 sqft
• 3530 evening star drive, Winter Haven 33881 $315,000 · 4 bd · 2 ba · 1,822 sqft
• 5337 hogan lane, Winter Haven 33884 $355,000 · 3 bd · 2 ba · 1,833 sqft
• 1496 33rd street northwest, Winter Haven 33881 $94,900 · 2 bd · 1 ba · 720 sqft
• 1454 austin street, Winter Haven 33884 $320,000 · 5 bd · 3 ba · 2,254 sqft
• 6549 crescent loop, Winter Haven 33884 $300,000 · 4 bd · 3 ba · 1,883 sqft
• 2711 gladiola road, Winter Haven 33884 $254,900 · 3 bd · 3 ba · 1,673 sqft
• 1738 hummingbird road, Winter Haven 33884 $314,900 · 4 bd · 2 ba · 1,720 sqft
• 3129 avenue west northwest, Winter Haven 33881 $230,000 · 3 bd · 1 ba · 1,500 sqft
• 1525 oakview circle southeast, Winter Haven 33880 $199,000 · 2 bd · 2 ba · 1,333 sqft
• 406 saint anns drive, Winter Haven 33884 $235,000 · 3 bd · 2 ba · 1,252 sqft
• 1061 sawgrass drive, Winter Haven 33884 $449,900 · 3 bd · 2 ba · 2,069 sqft
• 4242 cedarwood street, Winter Haven 33880 $120,000 · 2 bd · 2 ba · 1,056 sqft
• 5308 green drive, Winter Haven 33884 $255,000 · 3 bd · 2 ba · 1,495 sqft
• 1858 4th street southeast, Winter Haven 33880 $220,000 · 5 bd · 3 ba · 2,100 sqft
• 232 lake lucerne way, Winter Haven 33881 $275,000 · 3 bd · 2 ba · 1,965 sqft
• 321 alexzander way, Winter Haven 33881 $355,000 · 5 bd · 3 ba · 2,696 sqft
• 1642 teagan lane, Winter Haven 33884 $329,900 · 4 bd · 3 ba · 1,896 sqft
• 2216 starboard, Winter Haven 33881 $215,000 · 3 bd · 3 ba · 1,549 sqft
• 2230 west central avenue, Winter Haven 33880 $324,700 · 3 bd · 2 ba · 1,788 sqft
• 406 lake daisy drive, Winter Haven 33884 $259,900 · 3 bd · 2 ba · 1,406 sqft
• 1405 28th street northwest, Winter Haven 33881 $225,000 · 2 bd · 1 ba · 1,137 sqft