Recent studies found that providing low threshold access to housing increased housing stability in individuals experiencing long-term homelessness. The Housing First model, traditionally designed to assist those with complex needs, has become increasingly popular in North America and elsewhere. This study used data from semi-structured interviews with fifteen men who were enrolled in and received assistance with finding, financing and maintaining housing through a Housing First program called Transitions to Home (T2H) in Hamilton, Ontario, Canada. The objective of this paper was to describe men’s understandings, definitions, and experiences of housing stability once housed. When asked to provide definitions of stability, many of the men referred to factors associated with the concept of home such as comfort, safety and independence. We found that men’s descriptions of “housing stability” and “home” were multifaceted and included elements not traditionally captured in typical definitions of housing stability. The findings point to the importance of providing client-driven supports to assist men in achieving their ideal stable home environments.