Homes under $500K in Winter Haven, FL
660 for sale · 1,489 homes listed · Updated November 9, 2026 · Page 2 of 30
- 1340 Daisy Field Drive, Winter Haven 33884 $310,000 · 4 bd · 2 ba · 1,882 sqft
- 317 Avenue G Southeast, Winter Haven 33880 $239,900 · 4 bd · 3 ba · 1,610 sqft
- 221 Avenue C Northeast, Winter Haven 33881 $215,000 · 3 bd · 2 ba · 720 sqft
- 5009 Strada Drive, Winter Haven 33880 $415,000 · 4 bd · 3 ba · 2,434 sqft
- 5584 Taverna Loop, Winter Haven 33884 $274,470 · 3 bd · 2 ba · 1,504 sqft
- 1700 6th Street Northwest #A38, Winter Haven 33881 $78,800 · 2 bd · 1 ba · 840 sqft
- 128 North Lake Florence Drive, Winter Haven 33884 $384,900 · 3 bd · 2 ba · 2,167 sqft
- 2500 21st Street Northwest #22, Winter Haven 33881 $178,490 · 2 bd · 3 ba · 1,334 sqft
- 4123 Island Lakes Drive, Winter Haven 33881 $470,000 · 4 bd · 2 ba · 1,990 sqft
- 151 1st Street, Winter Haven 33880 $249,000 · 3 bd · 2 ba · 1,259 sqft
- 1746 Hummingbird Road, Winter Haven 33884 $326,150 · 3 bd · 2 ba · 1,593 sqft
- 1024 31st Street Northwest, Winter Haven 33881 $245,000 · 4 bd · 2 ba · 1,532 sqft
- 221 Golf Aire Boulevard, Winter Haven 33884 $275,000 · 3 bd · 2 ba · 1,645 sqft
- 6081 Southern Oaks Drive Southeast, Winter Haven 33884 $169,500 · 2 bd · 2 ba · 1,080 sqft
- 136 Krenson Bay Loop, Winter Haven 33881 $272,990 · 3 bd · 2 ba · 1,698 sqft
- 3971 Cypress Landing West, Winter Haven 33884 $288,900 · 3 bd · 2 ba · 1,674 sqft
- 302 Avenue P Northwest, Winter Haven 33881 $499,999 · 6 bd · 4 ba · 2,820 sqft
- 194 South Lake Mariam Drive, Winter Haven 33884 $390,000 · 2 bd · 2 ba · 1,538 sqft
- 357 Squires Grove Drive, Winter Haven 33880 $244,900 · 3 bd · 2 ba · 1,616 sqft
- 1207 32nd Street Northwest, Winter Haven 33881 $225,000 · 3 bd · 1 ba · 1,189 sqft
- 1700 6th Street Northwest #C31, Winter Haven 33881 $99,900 · 2 bd · 2 ba · 840 sqft
- 139 Avenue G Southeast, Winter Haven 33880 $170,000 · 2 bd · 1 ba · 896 sqft
- 217 4th Jpv Street, Winter Haven 33880 $214,000 · 3 bd · 1 ba · 1,064 sqft
- 6631 Thornhill Road, Winter Haven 33880 $320,000 · 3 bd · 2 ba · 1,221 sqft
- 4132 Martindale Loop, Winter Haven 33884 $399,900 · 4 bd · 3 ba · 1,894 sqft
- 410 Laurel Cove Way, Winter Haven 33884 $209,000 · 2 bd · 2 ba · 1,090 sqft
- 3408 Costello Circle, Winter Haven 33884 $315,000 · 4 bd · 2 ba · 1,713 sqft
- 1015 Carefree Cove Drive, Winter Haven 33881 $199,900 · 4 bd · 2 ba · 1,104 sqft
- 576 Ituna Circle, Winter Haven 33881 $309,900 · 3 bd · 2 ba · 1,545 sqft
- 540 Ituna Circle, Winter Haven 33881 $339,900 · 4 bd · 3 ba · 2,029 sqft
- 3339 Queens Cove Loop, Winter Haven 33880 $234,900 · 3 bd · 2 ba · 1,158 sqft
- 4246 Cedarwood Street, Winter Haven 33880 $99,000 · 2 bd · 2 ba · 1,008 sqft
- 820 26th Street Northwest, Winter Haven 33881 $249,000 · 3 bd · 2 ba · 1,122 sqft
- 8304 Waterview Way #8304, Winter Haven 33884 $154,900 · 2 bd · 2 ba · 930 sqft
- 1738 Hummingbird Road, Winter Haven 33884 $334,400 · 4 bd · 2 ba · 1,720 sqft
- 1757 Hummingbird Road, Winter Haven 33884 $423,900 · 4 bd · 3 ba · 2,336 sqft
- 333 Lake Howard Drive Northwest #211b, Winter Haven 33880 $149,900 · 3 bd · 2 ba · 1,218 sqft
- 1660 Hummingbird Road, Winter Haven 33884 $302,400 · 3 bd · 2 ba · 1,593 sqft
- 609 Lucerne Boulevard, Winter Haven 33881 $318,000 · 4 bd · 2 ba · 1,981 sqft
- 105 Laurel Cove Way #105, Winter Haven 33884 $189,000 · 2 bd · 2 ba · 1,090 sqft
- 265 Majestic Gardens Lane, Winter Haven 33880 $294,999 · 3 bd · 2 ba · 1,951 sqft
- 1500 Avenue G Northeast, Winter Haven 33881 $359,000 · 3 bd · 2 ba · 2,280 sqft
- 3695 Julius Estates Boulevard, Winter Haven 33881 $305,000 · 4 bd · 2 ba · 1,842 sqft
- 4919 St James Drive, Winter Haven 33881 $294,900 · 3 bd · 2 ba · 1,577 sqft
- 501 Avenue G Southeast, Winter Haven 33880 $319,900 · 4 bd · 2 ba · 1,816 sqft
- 2362 Brassie Court, Winter Haven 33884 $265,000 · 3 bd · 2 ba · 1,260 sqft
- 116 Harbor Drive, Winter Haven 33881 $289,900 · 4 bd · 2 ba · 1,476 sqft
- 790 Avenue Q Southeast, Winter Haven 33880 $185,000 · 2 bd · 1 ba · 934 sqft
- 5764 Royal Hills Circle, Winter Haven 33881 $324,000 · 4 bd · 3 ba · 2,278 sqft
- 218 5th Jpv Street, Winter Haven 33880 $223,900 · 5 bd · 2 ba · 1,240 sqft