Background: The majority of older adults prefer to remain in their homes, or to “age-in-place.” To accomplish this goal, many older adults will rely upon home- and community-based services (HCBS) for support. However, the availability and accessibility of HCBS may differ based on whether the older adult lives in the community or in a senior housing apartment facility. Methods: This paper reports findings from the Pathways to Life Quality study of residential change and stability among seniors in upstate New York. Data were analyzed from 663 older adults living in one of three housing types: service-rich facilities, service-poor facilities, and community-dwelling in single-family homes. A multinomial logistic regression model was used to examine factors associated with residence type. A linear regression model was fitted to examine factors associated with HCBS utilization. Results: When compared to community-dwelling older adults, those residing in service-rich and service-poor facilities were more likely to be older, report more activity limitations, and provide less instrumental assistance to others. Those in service-poor facilities were more likely to have poorer mental health and lower perceived purpose in life. The three leading HCBS utilized were senior centers (20%), homemaker services (19%), and transportation services (18%). More HCBS utilization was associated with participants who resided in service-poor housing, were older, were female, and had more activity limitations. More HCBS utilization was also associated with those who received instrumental support, had higher perceived purpose in life, and poorer mental health. Conclusions: Findings suggest that older adults’ residential environment is associated with their health status and HCBS utilization. Building upon the Person–Environment Fit theories, dedicated efforts are needed to introduce and expand upon existing HCBS available to facility residents to address physical and mental health needs as well as facilitate aging-in-place.