Homes under $500K in Winter Haven, FL
660 for sale · 1,489 homes listed · Updated November 9, 2026 · Page 1 of 30
- 657 Ave C Southwest, Winter Haven 33880 $250,000 · 3 bd · 2 ba · 1,144 sqft
- 934 Cattleman Street, Winter Haven 33884 $350,000 · 5 bd · 3 ba · 2,215 sqft
- 469 Muirfield Court, Winter Haven 33884 $299,999 · 2 bd · 2 ba · 1,293 sqft
- 3829 Giorgio, Winter Haven 33884 $242,000 · 3 bd · 2 ba
- 3180 Country Club Circle, Winter Haven 33881 $260,000 · 3 bd · 2 ba · 1,732 sqft
- 330 Sterling Drive, Winter Haven 33884 $295,000 · 3 bd · 2 ba · 1,426 sqft
- 920 Cambridge Drive, Winter Haven 33881 $270,000 · 4 bd · 2 ba · 1,846 sqft
- 173 Tracy Circle, Winter Haven 33884 $310,000 · 3 bd · 2 ba · 1,788 sqft
- 412 Northeast Avenue M Northeast, Winter Haven 33881 $258,500 · 3 bd · 2 ba · 1,451 sqft
- 304 Corso Loop, Winter Haven 33884 $220,000 · 3 bd · 2 ba
- 4179 Rolling Oaks Drive, Winter Haven 33880 $104,900 · 2 bd · 2 ba · 1,056 sqft
- 220 King Road, Winter Haven 33880 $110,000 · 2 bd · 1 ba · 672 sqft
- 2579 Sage Valley Way, Winter Haven 33884 $305,000 · 3 bd · 2 ba · 1,535 sqft
- 909 Cambridge Drive, Winter Haven 33881 $236,900 · 3 bd · 2 ba · 1,506 sqft
- 329 Lake Daisy Loop, Winter Haven 33884 $320,000 · 3 bd · 2 ba · 1,563 sqft
- 1581 Oakview Circle Southeast, Winter Haven 33880 $210,000 · 2 bd · 2 ba · 1,220 sqft
- 300 Meredith Boulevard, Winter Haven 33881 $294,990 · 4 bd · 2 ba · 1,758 sqft
- 3022 Hickory Street Northwest, Winter Haven 33881 $265,000 · 3 bd · 1 ba · 1,602 sqft
- 700 Mirror Terrace Northwest #507, Winter Haven 33881 $159,900 · 2 bd · 2 ba · 1,351 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
- 380 Lake Smart Circle, Winter Haven 33881 $325,990 · 4 bd · 2 ba · 2,034 sqft
- 2215 Starboard Drive #29, Winter Haven 33881 $184,900 · 2 bd · 2 ba · 1,436 sqft
- 97 Parson Drive, Winter Haven 33884 $79,500 · 2 bd · 2 ba · 989 sqft
- 923 West Lake Cannon Drive Northwest, Winter Haven 33881 $240,000 · 3 bd · 2 ba · 1,375 sqft
- 605 Sarner Pass Way, Winter Haven 33881 $389,900 · 4 bd · 3 ba · 2,676 sqft
- 4212 Cedarwood Street, Winter Haven 33880 $129,900 · 2 bd · 2 ba · 1,265 sqft
- 1015 Corso Drive, Winter Haven 33884 $345,000 · 5 bd · 4 ba · 3,200 sqft
- 2824 San Marco Way, Winter Haven 33884 $272,800 · 3 bd · 2 ba · 2,006 sqft
- 255 Haines Boulevard, Winter Haven 33881 $275,000 · 4 bd · 2 ba · 1,793 sqft
- 4750 Osprey Way, Winter Haven 33881 $295,000 · 4 bd · 2 ba · 1,986 sqft
- 400 Bayou Road, Winter Haven 33884 $254,000 · 2 bd · 2 ba · 1,277 sqft
- 1114 Brimstone Circle, Winter Haven 33884 $399,000 · 4 bd · 3 ba · 2,476 sqft
- 21 Casarena Court, Winter Haven 33881 $285,000 · 2 bd · 3 ba · 2,045 sqft
- 603 Maggie Circle, Winter Haven 33880 $245,000 · 3 bd · 2 ba · 1,482 sqft
- 1710 Garden Lake Drive #1710, Winter Haven 33884 $170,000 · 2 bd · 2 ba · 1,103 sqft
- 851 Vienna Drive, Winter Haven 33884 $279,900 · 3 bd · 2 ba · 1,569 sqft
- 400 El Camino Drive #223, Winter Haven 33884 $59,900 · 1 bd · 1 ba · 850 sqft
- 1733 Sandalwood Circle Southwest, Winter Haven 33880 $250,000 · 3 bd · 2 ba · 1,075 sqft
- 1104 Tyler Loop, Winter Haven 33884 $299,000 · 3 bd · 2 ba · 1,540 sqft
- 1328 Daisy Field Drive, Winter Haven 33884 $375,000 · 5 bd · 3 ba · 2,696 sqft
- 1061 Sawgrass Drive, Winter Haven 33884 $449,900 · 3 bd · 2 ba · 2,069 sqft
- 1700 6th Street Northwest #C21, Winter Haven 33881 $92,000 · 2 bd · 2 ba · 840 sqft
- 109 Rebecca Drive Northeast, Winter Haven 33881 $239,500 · 3 bd · 2 ba · 1,560 sqft
- 2759 Gladiola Road, Winter Haven 33884 $290,490 · 3 bd · 3 ba · 1,673 sqft
- 2765 Gladiola Road, Winter Haven 33884 $292,990 · 3 bd · 3 ba · 1,673 sqft
- 3357 Timberline Road West, Winter Haven 33880 $255,000 · 4 bd · 2 ba · 1,675 sqft
- 1740 2nd Street Northeast, Winter Haven 33881 $225,000 · 3 bd · 2 ba · 1,683 sqft
- 700 Mirror Terrace Northwest #511, Winter Haven 33881 $149,900 · 2 bd · 2 ba · 1,190 sqft
- 1734 Hummingbird Road, Winter Haven 33884 $368,720 · 4 bd · 3 ba · 2,308 sqft