He served as assistant county attorney of Crawford County, Kansas, in 1927 and 1928 and county attorney in 1929 and 1930. He served as commissioner of public utilities of Girard 1933–1935. He served as commissioner of finance of Girard 1936–1938.
Winter was elected as a Republican to the Seventy-sixth and to the three succeeding Congresses (January 3, 1939 – January 3, 1947). He was an unsuccessful candidate for renomination in 1946. He returned to Girard, Kansas, and continued to practice law. He died in Pittsburg, Kansas, November 7, 1951 and is interred in Park Cemetery, Columbus, Kansas.