Homes under $300K in Winter Haven, FL
441 for sale · 807 homes listed · Updated September 25, 2026 · Page 1 of 17
- 5850 cypress gardens boulevard 304, Winter Haven 33884 $139,000 · 2 bd · 2 ba · 1,332 sqft
- 508 lakeside ranch way, Winter Haven 33881 $79,000 · 2 bd · 2 ba · 1,128 sqft
- 657 ave c southwest, Winter Haven 33880 $250,000 · 3 bd · 2 ba · 1,144 sqft
- 100 lakeside ranch drive, Winter Haven 33881 $120,000 · 2 bd · 2 ba · 1,176 sqft
- 1561 vienna square drive, Winter Haven 33884 $225,000 · 2 bd · 2 ba · 1,231 sqft
- 1787 white elephant loop, Winter Haven 33884 $279,900 · 3 bd · 2 ba · 1,526 sqft
- 441 san jose drive, Winter Haven 33884 $275,000 · 2 bd · 2 ba · 1,843 sqft
- 503 holt circle, Winter Haven 33880 $170,000 · 3 bd · 2 ba · 1,305 sqft
- 6044 grand oaks drive southeast, Winter Haven 33884 $145,000 · 2 bd · 2 ba · 1,248 sqft
- 689 lake howard drive northwest 1e, Winter Haven 33880 $124,000 · 2 bd · 2 ba · 1,050 sqft
- 235 hibiscus street, Winter Haven 33881 $274,400 · 5 bd · 3 ba · 2,527 sqft
- 123 osprey heights drive, Winter Haven 33880 $250,000 · 3 bd · 2 ba · 1,329 sqft
- 683 broadmoor circle 683, Winter Haven 33884 $193,000 · 2 bd · 2 ba · 1,139 sqft
- 2218 abbey road, Winter Haven 33880 $179,999 · 2 bd · 2 ba · 1,252 sqft
- 1703 linz court, Winter Haven 33884 $248,000 · 2 bd · 2 ba · 1,164 sqft
- 1224 vienna square drive, Winter Haven 33884 $215,000 · 2 bd · 2 ba · 1,118 sqft
- 3931 avenue r northwest, Winter Haven 33881 $185,000 · 3 bd · 2 ba · 928 sqft
- 119 allen avenue, Winter Haven 33880 $240,000 · 4 bd · 2 ba · 1,520 sqft
- 4246 cedarwood street, Winter Haven 33880 $99,000 · 2 bd · 2 ba · 1,008 sqft
- 95 parson drive, Winter Haven 33884 $75,000 · 3 bd · 2 ba · 1,176 sqft
- 14 enclave drive, Winter Haven 33884 $219,900 · 2 bd · 2 ba · 1,368 sqft
- 3923 baldwin lane, Winter Haven 33884 $253,900 · 3 bd · 2 ba · 1,719 sqft
- 2817 wingfoot court, Winter Haven 33884 $270,000 · 3 bd · 2 ba · 1,666 sqft
- 601 avenue u northeast, Winter Haven 33881 $199,900 · 2 bd · 1 ba · 1,274 sqft
- 1997 26th street northwest, Winter Haven 33881 $189,900 · 3 bd · 2 ba · 1,166 sqft
- 1709 linz court, Winter Haven 33884 $248,000 · 2 bd · 2 ba · 1,164 sqft
- 3715 avenue j northwest, Winter Haven 33881 $217,000 · 3 bd · 2 ba · 892 sqft
- 3307 fox ridge drive, Winter Haven 33884 $235,000 · 4 bd · 2 ba · 1,253 sqft
- 136 madera drive, Winter Haven 33880 $171,380 · 3 bd · 2 ba · 1,448 sqft
- 602 taylor boulevard, Winter Haven 33880 $220,000 · 3 bd · 2 ba · 1,242 sqft
- 3843 eloise estates court, Winter Haven 33881 $280,000 · 3 bd · 2 ba · 1,600 sqft
- 1740 2nd street northeast, Winter Haven 33881 $225,000 · 3 bd · 2 ba · 1,683 sqft
- 649 broadmoor circle, Winter Haven 33884 $124,000 · 2 bd · 2 ba · 1,278 sqft
- 2307 scarlet avenue, Winter Haven 33884 $260,000 · 3 bd · 2 ba · 1,343 sqft
- 1601 roselawn street southwest, Winter Haven 33880 $256,500 · 2 bd · 1 ba · 1,099 sqft
- 6033 grand oaks drive southeast, Winter Haven 33884 $129,900 · 2 bd · 2 ba · 1,120 sqft
- 400 el camino drive 223, Winter Haven 33884 $59,900 · 1 bd · 1 ba · 850 sqft
- 200 black skimmer lane, Winter Haven 33880 $285,000 · 3 bd · 2 ba · 1,265 sqft
- 6315 grove pointe drive southeast, Winter Haven 33884 $158,000 · 2 bd · 2 ba · 1,248 sqft
- 2739 rutledge court, Winter Haven 33884 $214,000 · 3 bd · 2 ba · 1,419 sqft
- 1864 emily drive, Winter Haven 33884 $287,500 · 4 bd · 2 ba · 1,836 sqft
- 2270 firestone place, Winter Haven 33884 $180,000 · 2 bd · 2 ba · 1,439 sqft
- 511 marcia loop, Winter Haven 33884 $259,900 · 4 bd · 3 ba · 2,159 sqft
- 3349 costello circle, Winter Haven 33884 $237,490 · 3 bd · 2 ba · 1,516 sqft
- 109 rebecca drive northeast, Winter Haven 33881 $239,500 · 3 bd · 2 ba · 1,560 sqft
- 469 muirfield court, Winter Haven 33884 $299,999 · 2 bd · 2 ba · 1,293 sqft
- 4251 cedarwood street, Winter Haven 33880 $106,000 · 2 bd · 2 ba · 1,216 sqft
- 3022 hickory street northwest, Winter Haven 33881 $265,000 · 3 bd · 1 ba · 1,602 sqft
- 4165 rolling oaks drive, Winter Haven 33880 $84,900 · 2 bd · 2 ba · 1,152 sqft
- 440 kensington view drive, Winter Haven 33880 $269,000 · 3 bd · 2 ba · 1,688 sqft