Winter graduated from Traverse City High School (1905); attended Olivet College (1906-07); and the Chicago Academy of Fine Arts under Wellington J. Reynolds (1908-11). In 1911 he won the Prix de Rome which enabled him to study at the American Academy in Rome for three years. After some extended travel in Europe he returned to the United States in 1916.
Winter was primarily a muralist. His most famous work is the huge mural in the grand foyer of Radio City Music Hall in Rockefeller Center titled "Author of Life" or "Fountain of Youth." Other murals include those in the Cunard Building, New York City; Cornell University; New York Cotton Exchange; National Chamber of Commerce, Washington, DC; Union Trust Building, Detroit, Michigan; Clark Memorial, Vincennes, Indiana; Eastman Theatre, Rochester, New York; and the Library of Congress.
Winter married Vera Beaudette in 1911, whom he divorced in 1922. In 1932 he married Mrs. Patricia Murphy. During World War I, Winter designed camouflage for the U.S. Shipping Board. Winter committed suicide. A retrospective of his work was held at the Berkshire Museum in 1955.
To qualify as Academician, Winter submitted a watercolor, "Study for a Mural Decoration for the Cunard Office."
