Born in Coalinga, California, in 1929, Barbara Winkelstein lived in Venezuela and Colorado before earning her BA at the University of Oregon, in 1950. She moved to San Francisco in 1956, where she met and married architect Peter Winkelstein. Together, they raised three children.

Barbara was a prolific and lauded professional portrait painter, known for capturing the essence of her subjects - many of whom would become lifelong friends. She also painted watercolors and oils of the California landscapes she loved, including Stinson Beach, Tennessee Valley, and Echo Lake. In her later years, she shared a Pier 70 studio with a close group of women artists who gathered there to paint portraits of live models. Her work has been shown at various galleries and at Open Studios in San Francisco, and graces the homes of the many clients and friends with whom she shared her life and art.