Purpose: Women comprise almost one-third of academic medicine faculty 60 years of age and older. Gender disparities have been documented across many measures in medicine, including salary, promotion rates, and leadership positions and may impact long-term career and retirement decisions. The authors sought to describe gender differences in retirement decisions among late-career, full-time medical school faculty. Materials and Methods: The authors conducted a secondary analysis of cross-sectional survey data from a 2017 survey of faculty 55 years of age and older at 14 U.S. Medical Schools. Responses were compared for differences by gender using bivariate and multivariable analyses. Results: Among the 2,126 respondents (41% response rate), the majority were male (67%) and the average age was 62. Less than half (45%) had current plans to retire and 50% reported that they would consider working part time. Women faculty were less likely to be professors or on a tenure track and more likely to be single and report past and current caregiving responsibilities. Women differed from men in the personal and professional factors influencing retirement decisions with women more likely to identify health insurance, sense of burnout, lack of access to career advancing resources and opportunities, feeling devalued at work, and caregiving responsibilities as important issues. Conclusions: Women late-career faculty report unique and salient factors influencing retirement plans that may reflect cumulative gender-based career differences and disparities. Institutions should be aware of these differences and work to support women during late career and retirement transitions, including creating opportunities for faculty to remain engaged in meaningful work during retirement transitions if they desire to do so.