Single‐site Housing First (HF) entails the provision of immediate, permanent, low‐barrier supportive housing to chronically homeless individuals within a single building. Studies have shown that greater time spent in HF is associated with reduced publicly funded service utilization and improved health outcomes, but more research is needed to clarify how HF programs might maximize housing stability. In this study, semistructured, qualitative interviews were conducted (N = 11) to document the experiences of continuously and discontinuously housed residents of single‐site HF. Grounded theory methods led to the identification of 3 dialectic themes: sense of community (seeking connection while seeking space), stability (seeking stability while having concerns about stagnation), and control (gaining autonomy while relinquishing control). Findings suggest that the community environment and the stability offered by single‐site HF support longer stays in housing and that ensuring adequate privacy and providing additional programming could further enhance residents’ ability to remain stably housed.