Homes under $500K in Winter Haven, FL
540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 5 of 36
- 1100 carefree cove drive, Winter Haven 33881 $200,000 · 3 bd · 2 ba · 1,019 sqft
- 101 sandburg lane, Winter Haven 33884 $309,000 · 4 bd · 2 ba · 1,925 sqft
- 1328 3rd street northeast, Winter Haven 33881 $199,999 · 3 bd · 2 ba · 1,118 sqft
- 3329 fox ridge drive, Winter Haven 33884 $259,900 · 3 bd · 2 ba · 1,317 sqft
- 3735 imperial drive, Winter Haven 33880 $244,900 · 3 bd · 2 ba · 1,393 sqft
- 406 lake daisy drive, Winter Haven 33884 $249,900 · 3 bd · 2 ba · 1,406 sqft
- listing-10668990118, Winter Haven 33881 $315,000 · 3 bd · 2 ba · 1,220 sqft
- 1210 32nd street northwest, Winter Haven 33881 $179,900 · 3 bd · 1 ba · 936 sqft
- 545 reddicks circle, Winter Haven 33884 $220,000 · 4 bd · 2 ba · 1,655 sqft
- 3005 captain jax way, Winter Haven 33884 $245,140 · 3 bd · 3 ba · 1,423 sqft
- 3915 avenue q northwest, Winter Haven 33881 $109,900 · 3 bd · 2 ba · 860 sqft
- 2710 woodlawn drive, Winter Haven 33881 $199,000 · 3 bd · 1 ba · 1,092 sqft
- 996 summer glen drive, Winter Haven 33880 $294,900 · 4 bd · 2 ba · 1,851 sqft
- 304 lake lucerne way, Winter Haven 33881 $210,000 · 5 bd · 2 ba · 2,618 sqft
- 121 bates avenue southeast, Winter Haven 33880 $179,000 · 2 bd · 1 ba · 1,080 sqft
- 6604 winterset gardens road, Winter Haven 33884 $399,900 · 4 bd · 3 ba · 2,459 sqft
- 1475 grand cayman circle, Winter Haven 33884 $359,000 · 3 bd · 2 ba · 2,066 sqft
- 689 lake howard drive northwest #1e, Winter Haven 33880 $124,000 · 2 bd · 2 ba · 1,050 sqft
- 1117 michelangelo lane, Winter Haven 33884 $375,000 · 4 bd · 3 ba · 2,626 sqft
- 1313 fairfax street northeast, Winter Haven 33881 $265,000 · 3 bd · 2 ba · 1,145 sqft
- 617 wexford court, Winter Haven 33884 $230,000 · 2 bd · 2 ba · 1,286 sqft
- 123 osprey heights drive, Winter Haven 33880 $250,000 · 3 bd · 2 ba · 1,329 sqft
- 1561 vienna square drive, Winter Haven 33884 $225,000 · 2 bd · 2 ba · 1,231 sqft
- 6315 grove pointe drive southeast, Winter Haven 33884 $158,000 · 2 bd · 2 ba · 1,248 sqft
- 372 lake daisy circle, Winter Haven 33884 $310,000 · 4 bd · 2 ba · 1,907 sqft
- 974 lunar lane, Winter Haven 33884 $341,066 · 4 bd · 2 ba · 1,816 sqft
- 951 lunar lane, Winter Haven 33884 $304,016 · 3 bd · 2 ba · 1,447 sqft
- 3843 eloise estates court, Winter Haven 33881 $280,000 · 3 bd · 2 ba · 1,600 sqft
- 4158 rolling oaks drive, Winter Haven 33880 $124,900 · 2 bd · 2 ba · 1,403 sqft
- 1755 beth lane, Winter Haven 33880 $435,000 · 3 bd · 2 ba · 2,702 sqft
- 645 broadmoor circle #645, Winter Haven 33884 $169,000 · 2 bd · 2 ba · 1,278 sqft
- 4807 plumwood street, Winter Haven 33880 $110,000 · 2 bd · 2 ba · 1,104 sqft
- 180 solis drive, Winter Haven 33880 $268,520 · 3 bd · 2 ba · 1,460 sqft
- 4228 cedarwood street, Winter Haven 33880 $118,000 · 2 bd · 2 ba · 1,104 sqft
- 1406 meadow drive northeast, Winter Haven 33881 $225,000 · 3 bd · 2 ba · 1,678 sqft
- 607 country lane northeast #607, Winter Haven 33881 $142,500 · 2 bd · 2 ba · 1,252 sqft
- 4132 sprucewood street, Winter Haven 33880 $129,000 · 2 bd · 2 ba · 1,344 sqft
- 108 lagoon road, Winter Haven 33884 $340,000 · 3 bd · 2 ba · 1,735 sqft
- 919 avenue south southeast, Winter Haven 33880 $330,000 · 3 bd · 2 ba · 1,751 sqft
- 257 meadowbrook boulevard, Winter Haven 33881 $279,975 · 3 bd · 2 ba · 1,725 sqft
- 1105 eagle pond drive #1105, Winter Haven 33884 $165,000 · 2 bd · 2 ba · 1,017 sqft
- 344 alexzander way, Winter Haven 33881 $385,000 · 5 bd · 3 ba · 2,696 sqft
- 4913 kaia avenue, Winter Haven 33884 $325,000 · 3 bd · 2 ba · 1,300 sqft
- 4234 rolling oaks drive, Winter Haven 33880 $139,900 · 2 bd · 2 ba · 1,804 sqft
- 4239 cedarwood street, Winter Haven 33880 $125,000 · 2 bd · 2 ba · 1,368 sqft
- 4 enclave drive, Winter Haven 33884 $240,000 · 3 bd · 2 ba · 1,526 sqft
- 4173 rolling oaks drive, Winter Haven 33880 $95,000 · 2 bd · 2 ba · 720 sqft
- 4577 back nine drive, Winter Haven 33884 $334,800 · 3 bd · 2 ba · 1,918 sqft
- 5197 pebble beach boulevard, Winter Haven 33884 $335,000 · 2 bd · 2 ba · 1,677 sqft
- 4253 cedarwood street, Winter Haven 33880 $99,000 · 2 bd · 2 ba · 1,056 sqft