Homes under $300K in Winter Haven, FL

333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 12 of 23

• 1144 high seas street, Winter Haven 33880 Active Under Contract $289,900 · 3 bd · 2 ba · 1,716 sqft
• 650 avenue north southeast, Winter Haven 33880 Active Under Contract $225,000 · 4 bd · 3 ba · 1,839 sqft
• 1040 cambridge drive, Winter Haven 33881 Active Under Contract $235,000 · 3 bd · 2 ba · 1,727 sqft
• 505 glad road, Winter Haven 33880 Active Under Contract $239,900 · 3 bd · 2 ba · 1,270 sqft
• 4925 jackson street, Winter Haven 33884 Active Under Contract $249,900 · 3 bd · 2 ba · 1,425 sqft
• 2771 gladiola road, Winter Haven 33884 Active Under Contract $273,990 · 3 bd · 3 ba · 1,758 sqft
• 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
• 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
• 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
• 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
• 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
• 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
• 2824 san marco way, Winter Haven 33884 Active Under Contract $225,000 · 3 bd · 2 ba · 2,006 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
• 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
• 3722 fieldstone circle, Winter Haven 33881 Active Under Contract $298,900 · 4 bd · 2 ba · 1,835 sqft
• 5872 red fox drive, Winter Haven 33884 Active Under Contract $175,000 · 3 bd · 2 ba · 1,344 sqft
• 1668 roselawn street southwest, Winter Haven 33880 Active Under Contract $219,900 · 3 bd · 1 ba · 1,100 sqft
• 3729 fieldstone circle, Winter Haven 33881 Active Under Contract $290,000 · 4 bd · 2 ba · 1,797 sqft
• 136 whitman road, Winter Haven 33884 Active Under Contract $239,500 · 3 bd · 2 ba · 1,319 sqft
• 288 cherry laurel lane, Winter Haven 33880 Active Under Contract $235,000 · 3 bd · 2 ba · 1,276 sqft
• 209 avenue c northeast, Winter Haven 33881 Active Under Contract $180,000 · 3 bd · 2 ba · 1,000 sqft
• 4112 sprucewood street, Winter Haven 33880 Active Under Contract $119,900 · 2 bd · 2 ba · 912 sqft