Research on programs offering senior-specific housing supports and enabling “aging in the right place” (AIRP) for “older persons with experiences of homelessness” (OPEH) is limited. This paper presents an environmental assessment of a “transitional housing program” (THP) in Metro Vancouver, Canada, for OPEH to AIRP. Data were collected using Aging in the Right Place Environmental (AIRP-ENV) and Secondary Observation (AIRP-ENV-SO) audit tools designed to evaluate multi-unit housing for OPEH. The 241-item AIRP-ENV tool was used to assess the built environmental features of four multi-unit buildings of the THP. The AIRP-ENV-SO tool was used to collect contextual data on the function, safety, and land use of the surrounding neighborhood. Findings identified built environment and urban design features that support THP residents’ safety, security, accessibility, functionality, social activity, autonomy, and identity. The THP buildings were rated ‘Good’ for accessibility, functionality, autonomy and identity, while ‘Satisfactory’ or ‘Poor’ for safety, security, and social activity. Findings point to the built environmental features (e.g., size and layout of spaces) required in the THP to create opportunities for increased social engagement among residents and enhanced safety and security. The AIRP-ENV and AIRP-ENV-SO audit tools can help inform programs across the housing continuum to develop supportive built environments that promote AIRP for OPEH.