Heilbrun enjoyed solitude when working and, despite being a wife and mother of three, often spent time alone at various retreats over the years, including her luxury Manhattan apartment and a country home in upstate New York. She also had a Summer house in Alford, Massachusetts. At the age of 68, she purchased a new home to use by herself, as she wanted a private place. She held strong opinions on nearly every aspect of women's lives and also believed that ending one's own life was a basic human right. In keeping with her views on aging in "The Last Gift of Time: Life Beyond Sixty", she quit wearing high heels, hose, and form-fitting clothing in her early 60s. She adopted blouses and slacks as her daily attire. Heilbrun's son recalled, "My mother was a generous hostess when she was young, but lost interest in dinner parties as she got older. She preferred to order groceries from the local supermarket and have them sent to her apartment as she was too busy to waste time squeezing oranges at Fairway."