Within the areas of literature on both population aging and health and homelessness, little attention has been given to the opportunities and barriers to healthy aging among older persons with a history of homelessness. Set in the context of inner-city Toronto, Canada, this article reports on the findings from qualitative interviews with 29 formerly homeless older persons. The findings illustrate participants' experiences of positive health change since moving into a stable housing environment and the aspects of housing they perceive to have improved their health and wellbeing. The qualitative findings also draw attention to the ongoing barriers to healthy aging that can be experienced among older persons with a history of homelessness. Overall, this study draws on the lived experiences of formerly homeless older persons to offer a better understanding of the long-term effects of homelessness on health, wellbeing, and aging.