Homes under $500K in Winter Haven, FL
540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 24 of 36
- 5125 sylas jax avenue, Winter Haven 33884 Off market since Sep 2026 $259,900 · 3 bd · 2 ba · 1,358 sqft
- 4918 rosewood street, Winter Haven 33880 Off market since Sep 2026 $125,000 · 2 bd · 2 ba · 1,008 sqft
- 144 morning glory circle, Winter Haven 33884 Off market since Sep 2026 $279,000 · 3 bd · 2 ba · 1,433 sqft
- 607 country lane northeast 607, Winter Haven 33881 Off market since Sep 2026 $142,500 · 2 bd · 2 ba · 1,252 sqft
- 5444 san pietro drive, Winter Haven 33884 Off market since Sep 2026 $314,999 · 4 bd · 3 ba · 2,226 sqft
- 220 king road, Winter Haven 33880 Off market since Sep 2026 $119,000 · 2 bd · 1 ba · 672 sqft
- 900 lake jessie drive, Winter Haven 33881 Off market since Sep 2026 $410,000 · 3 bd · 3 ba · 1,828 sqft
- 551 lake smart boulevard, Winter Haven 33881 Off market since Sep 2026 $334,900 · 4 bd · 2 ba · 1,936 sqft
- 321 orange blossom drive, Winter Haven 33880 Off market since Sep 2026 $199,950 · 2 bd · 3 ba · 1,407 sqft
- 5347 mickey avenue, Winter Haven 33884 Off market since Sep 2026 $334,999 · 4 bd · 3 ba · 2,077 sqft
- 213 cleveland avenue, Winter Haven 33881 Off market since Sep 2026 $180,000 · 2 bd · 1 ba · 728 sqft
- 2105 9th street northeast, Winter Haven 33881 Off market since Sep 2026 $239,000 · 3 bd · 1 ba · 1,042 sqft
- 1522 eckart drive, Winter Haven 33881 Off market since Sep 2026 $349,999 · 3 bd · 2 ba · 1,524 sqft
- 6450 hollyberry lane northeast, Winter Haven 33881 Off market since Sep 2026 $151,000 · 2 bd · 2 ba · 1,144 sqft
- 125 lake hazel drive, Winter Haven 33884 Off market since Sep 2026 $100,000 · 2 bd · 2 ba · 1,056 sqft
- 6773 brentwood drive northeast, Winter Haven 33881 Off market since Sep 2026 $139,900 · 2 bd · 2 ba · 1,056 sqft
- 507 sharon hill court, Winter Haven 33880 Off market since Aug 2026 $254,999 · 4 bd · 2 ba · 2,356 sqft
- 236 west lake ina drive, Winter Haven 33881 Off market since Jul 2026 $430,000 · 3 bd · 4 ba · 2,576 sqft
- 2500 21st street northwest 15, Winter Haven 33881 Off market since Sep 2026 $170,000 · 2 bd · 3 ba · 1,184 sqft
- 1382 salisbury drive, Winter Haven 33881 Off market since Sep 2026 $293,899 · 4 bd · 3 ba · 1,764 sqft
- 6309 grove pointe drive southeast, Winter Haven 33884 Off market since Sep 2026 $154,000 · 2 bd · 2 ba · 1,248 sqft
- 542 eagle landing boulevard, Winter Haven 33880 Off market since Sep 2026 $257,000 · 3 bd · 2 ba · 1,292 sqft
- 4155 sprucewood street, Winter Haven 33880 Off market since Sep 2026 $115,000 · 2 bd · 2 ba · 1,200 sqft
- 1501 7th street southeast, Winter Haven 33880 Off market since Jul 2026 $360,000 · 5 bd · 3 ba · 2,806 sqft
- 131 ruby lake drive, Winter Haven 33884 Off market since Sep 2026 $359,000 · 3 bd · 2 ba · 1,914 sqft
- 1658 teagan lane, Winter Haven 33884 Off market since Sep 2026 $315,990 · 4 bd · 3 ba · 1,933 sqft
- 961 harold pass, Winter Haven 33884 Off market since Sep 2026 $247,990 · 3 bd · 2 ba · 1,432 sqft
- 204 kingshill court southeast, Winter Haven 33884 Off market since Sep 2026 $254,900 · 3 bd · 2 ba · 1,437 sqft
- 139 woden way, Winter Haven 33884 Off market since Jul 2026 $429,500 · 4 bd · 4 ba · 2,766 sqft
- 221 avenue f southeast, Winter Haven 33880 Sold on Jul 7, 2026 $185,000 · 2 bd · 2 ba · 804 sqft
- 6473 peppertree path northeast, Winter Haven 33881 Off market since Sep 2026 $146,000 · 2 bd · 2 ba · 1,107 sqft
- 144 beverly drive, Winter Haven 33884 Off market since Jul 2026 $389,900 · 4 bd · 3 ba · 2,492 sqft
- 4173 rolling oaks drive, Winter Haven 33880 Off market since Sep 2026 $95,000 · 2 bd · 2 ba · 720 sqft
- 231 avenue a northeast, Winter Haven 33881 Off market since Sep 2026 $195,000 · 3 bd · 1 ba · 1,144 sqft
- 1328 daisy field drive, Winter Haven 33884 Off market since Sep 2026 $380,000 · 5 bd · 3 ba · 2,696 sqft
- 2235 lakeridge drive, Winter Haven 33881 Off market since Jul 2026 $300,000 · 3 bd · 2 ba · 1,893 sqft
- 441 mckenna drive, Winter Haven 33881 Off market since Sep 2026 $335,000 · 4 bd · 3 ba · 2,360 sqft
- 4925 cypress gardens road 100, Winter Haven 33884 Off market since Jul 2026 $195,000 · 2 bd · 2 ba · 1,008 sqft
- 1392 axel circle, Winter Haven 33880 Off market since Jul 2026 $370,000 · 5 bd · 3 ba · 2,523 sqft
- 851 vienna drive, Winter Haven 33884 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,569 sqft
- 4140 sophia boulevard, Winter Haven 33880 Off market since Sep 2026 $255,000 · 3 bd · 2 ba · 1,711 sqft
- 292 arbuthnot street, Winter Haven 33881 Off market since Jul 2026 $299,900 · 3 bd · 2 ba · 1,305 sqft
- 2415 brassie court, Winter Haven 33884 Off market since Sep 2026 $289,900 · 3 bd · 2 ba · 1,629 sqft
- 1619 pearce road northwest, Winter Haven 33881 Off market since Sep 2026 $265,000 · 2 bd · 1 ba · 2,142 sqft
- 113 6th jpv street, Winter Haven 33880 Off market since Sep 2026 $250,000 · 3 bd · 2 ba · 1,035 sqft
- 2128 34th street northwest, Winter Haven 33881 Off market since Jul 2026 $190,000 · 4 bd · 2 ba · 1,437 sqft
- 665 broadmoor circle, Winter Haven 33884 Off market since Jul 2026 $170,000 · 2 bd · 2 ba · 1,139 sqft
- 800 ware avenue northeast, Winter Haven 33881 Off market since Sep 2026 $242,499 · 3 bd · 2 ba · 1,000 sqft
- 1783 white elephant loop, Winter Haven 33884 Off market since Sep 2026 $364,900 · 5 bd · 3 ba · 2,244 sqft
- 447 village circle southwest, Winter Haven 33880 Off market since Sep 2026 $145,000 · 2 bd · 2 ba · 1,000 sqft