Winters was first cast in the 1968 motion picture Me, Natalie, opposite Patty Duke, James Farentino, and Martin Balsam. She followed shortly afterwards with a second co-starring role opposite Michael Douglas in his first film, the 1969 Hail, Hero!, directed by David Miller. This was followed by a starring role in the CBS Playhouse production of The People Next Door which led to the motion picture remake the following year.