Homes under $500K in Winter Haven, FL

540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 18 of 36

• 207 winter ridge boulevard 4, Winter Haven 33881 Active Under Contract $145,000 · 2 bd · 2 ba · 1,073 sqft
• 524 haines trail, Winter Haven 33881 Active Under Contract $279,999 · 4 bd · 2 ba · 1,980 sqft
• 112 palm drive, Winter Haven 33880 Active Under Contract $172,900 · 2 bd · 2 ba · 720 sqft
• 212 overlook drive, Winter Haven 33884 Active Under Contract $250,000 · 3 bd · 2 ba · 1,731 sqft
• 417 corso loop, Winter Haven 33884 Active Under Contract $290,000 · 4 bd · 2 ba · 1,851 sqft
• 233 mandolin drive, Winter Haven 33884 Active Under Contract $320,000 · 4 bd · 2 ba · 1,767 sqft
• 13 cactus circle east, Winter Haven 33880 Active Under Contract $175,000 · 3 bd · 2 ba · 1,560 sqft
• 3328 avenue t northwest, Winter Haven 33881 Active Under Contract $189,990 · 3 bd · 1 ba · 1,208 sqft
• 4052 phoenician way, Winter Haven 33884 Active Under Contract $409,000 · 3 bd · 2 ba · 1,956 sqft
• 256 oleander street, Winter Haven 33881 Active Under Contract $250,000 · 3 bd · 2 ba · 1,450 sqft
• 4112 island lakes drive, Winter Haven 33881 Active Under Contract $250,000 · 3 bd · 2 ba · 1,686 sqft
• 200 el camino drive 311, Winter Haven 33884 Active Under Contract $90,500 · 2 bd · 2 ba · 1,378 sqft
• 144 beverly drive, Winter Haven 33884 Active Under Contract $409,900 · 4 bd · 3 ba · 2,492 sqft
• 4604 crystal beach road, Winter Haven 33880 Active Under Contract $328,500 · 3 bd · 2 ba · 1,258 sqft
• 3221 oak tree lane, Winter Haven 33884 Active Under Contract $349,900 · 3 bd · 2 ba · 1,722 sqft
• 118 browning circle, Winter Haven 33884 Active Under Contract $269,900 · 3 bd · 2 ba · 1,738 sqft
• 506 thomas avenue, Winter Haven 33880 Active Under Contract $235,000 · 4 bd · 2 ba · 1,656 sqft
• 679 lake dexter circle, Winter Haven 33884 Active Under Contract $337,000 · 2 bd · 2 ba · 1,186 sqft
• 177 fish hawk drive, Winter Haven 33884 Active Under Contract $349,000 · 6 bd · 5 ba · 3,920 sqft
• 6115 grey heron drive, Winter Haven 33881 Active Under Contract $315,000 · 6 bd · 3 ba · 2,701 sqft
• 1514 lake thomas loop, Winter Haven 33880 Active Under Contract $315,000 · 3 bd · 2 ba · 1,754 sqft
• 344 winter ridge boulevard 344, Winter Haven 33881 Active Under Contract $164,999 · 3 bd · 2 ba · 1,073 sqft
• 1079 sunshine way southwest, Winter Haven 33880 Active Under Contract $260,000 · 3 bd · 2 ba · 1,348 sqft
• 1725 31st street northwest, Winter Haven 33881 Active Under Contract $199,900 · 3 bd · 2 ba · 874 sqft
• 2638 san marco way, Winter Haven 33884 Active Under Contract $279,900 · 4 bd · 2 ba · 1,707 sqft
• 4027 rolling oaks drive, Winter Haven 33880 Active Under Contract $70,000 · 2 bd · 2 ba · 1,200 sqft
• 415 avenue east southeast, Winter Haven 33880 Active Under Contract $160,000 · 2 bd · 2 ba · 720 sqft
• 205 whitman road, Winter Haven 33884 Active Under Contract $289,900 · 3 bd · 2 ba · 1,434 sqft
• 4134 bedford avenue, Winter Haven 33884 Active Under Contract $309,000 · 3 bd · 2 ba · 1,941 sqft
• 140 morning glory circle, Winter Haven 33884 Active Under Contract $280,000 · 3 bd · 2 ba · 1,730 sqft
• 235 6th street northwest 205, Winter Haven 33881 Active Under Contract $149,500 · 2 bd · 1 ba · 873 sqft
• 128 center street, Winter Haven 33880 Active Under Contract $189,900 · 2 bd · 1 ba · 806 sqft
• 105 byron place, Winter Haven 33884 Active Under Contract $285,000 · 4 bd · 2 ba · 1,836 sqft
• 4519 ashford drive, Winter Haven 33880 Active Under Contract $385,000 · 3 bd · 3 ba · 2,039 sqft
• 2824 san marco way, Winter Haven 33884 Active Under Contract $225,000 · 3 bd · 2 ba · 2,006 sqft
• 404 coleman drive, Winter Haven 33884 Active Under Contract $320,000 · 3 bd · 2 ba · 1,940 sqft
• 26 saint kitts circle, Winter Haven 33884 Active Under Contract $230,000 · 3 bd · 2 ba · 1,954 sqft
• 1986 avenue f, Winter Haven 33880 Active Under Contract $184,999 · 2 bd · 1 ba · 885 sqft
• 651 hart lake drive, Winter Haven 33884 Active Under Contract $495,000 · 4 bd · 3 ba · 2,160 sqft
• 100 el camino drive 309, Winter Haven 33884 Active Under Contract $94,900 · 2 bd · 2 ba · 1,579 sqft
• 2207 avenue b northwest, Winter Haven 33880 Active Under Contract $150,000 · 4 bd · 2 ba · 1,568 sqft
• 1307 innsbruck court, Winter Haven 33884 Active Under Contract $197,900 · 2 bd · 2 ba · 1,316 sqft
• 112 terrace drive, Winter Haven 33884 Active Under Contract $279,900 · 3 bd · 2 ba · 1,659 sqft
• 106 saint kitts circle, Winter Haven 33884 Active Under Contract $269,900 · 3 bd · 2 ba · 1,534 sqft
• 5641 royal hills drive, Winter Haven 33881 Active Under Contract $299,990 · 4 bd · 2 ba · 2,010 sqft
• 244 winter ridge boulevard 244, Winter Haven 33881 Active Under Contract $99,900 · 2 bd · 2 ba · 1,073 sqft
• 5939 silver fox drive, Winter Haven 33884 Active Under Contract $160,000 · 3 bd · 2 ba · 1,248 sqft
• 695 22nd street northwest, Winter Haven 33880 Active Under Contract $234,900 · 3 bd · 2 ba · 1,708 sqft
• 2802 sunset drive northwest, Winter Haven 33881 Active Under Contract $269,900 · 3 bd · 2 ba · 1,576 sqft
• 5230 thornhill road, Winter Haven 33880 Active Under Contract $329,900 · 3 bd · 2 ba · 1,400 sqft