Winter Haven is located five miles north of Carrizo Springs on Farm Road 1407 in north central Dimmit County. The town was established in 1911 by Floridians, who named it after their home. Winter Haven was one of several new settlements in Dimmit County between 1909 and 1917. A post office opened in 1927. Eight businesses were reported in 1931, but only three in 1949; meanwhile, the population rose from fifty in 1939, the first year for which figures were available, to eighty in 1949. The town had no businesses by 1980. It had a population of 112 in 1990. The population remained the same in 2000.