Born in Beuthen, Upper Silesia (present-day Bytom, Poland), his family moved to Berlin after the Silesian Uprisings in 1921.
He studied violin and clarinet at the Academy of Music and played in jazz and swing dance orchestras to earn a living, later becoming a bandleader.
In 1948 he recorded the song Und jetzt ist es still, composed by Hans Lang, which, translated into English by Bert Reisfeld (It's Oh So Quiet), was covered by Betty Hutton in 1951 and popularized by Björk in 1995.
In the 1950s Winter performed in several revues and variety films with stars like Marika Rökk, but also played with jazz musicians like Hans Koller and Joe Zawinul.
His German entry Du hast mich so fasziniert (''You fascinated me so much'')" written by Robert Stolz finished seventh out of thirteen.