After the end of World War II, Winters moved to New York City in 1946 where he was almost immediately engaged for the Broadway musical revue Call Me Mister, portraying a variety of smaller roles.
He portrayed several more roles with the NYCO over the next seven years, including Dessalines in William Grant Still's Troubled Island (1949), the four villains in Jacques Offenbach's The Tales of Hoffmann (1949), Escamillo in Georges Bizet's Carmen (1949), Tchelio in Sergei Prokofiev's The Love for Three Oranges (1950), Tonio in Ruggero Leoncavallo's Pagliacci (1950), Timur in Giacomo Puccini's Turandot (1950), Alfio in Cavalleria rusticana (1950), The Messenger in the world premiere of David Tamkin's The Dybbuk (1951), the title role in Giuseppe Verdi's Rigoletto (1951), King Balthazar in Gian Carlo Menotti's Amahl and the Night Visitors (1952), Colline in Puccini's La bohème (1952), the title role in Béla Bartók's Bluebeard's Castle (1953), Count Almaviva in Mozart's The Marriage of Figaro (1954), Joe in Show Boat (1954), Germont in Verdi's La Traviata (1955), and Diomede in the New York premiere of William Walton's Troilus and Cressida (1955) among others.
In 1950 he joined the roster of principal baritones at the Royal Swedish Opera where he sang a number of roles for two seasons.
In 1957 Winters became a principal baritone on the roster at the Deutsche Oper Berlin where he spent most of his time performing in operas through 1961.
He also sang in a number of roles with the Vienna State Opera and the San Francisco Opera during these years, including the title role in Carl Orff's Die Kluge, Amonasro, Fritz Kothner in Die Meistersinger von Nürnberg, Tonio, and Wolfram in Tannhäuser.
He returned to the Hamburg State Opera in 1961, working as a principal baritone with the company until his untimely death at the age of 50 in 1965.