This study reports psychosocial characteristics of a sample of 111 children (K to 2nd grade) and their mothers who were living in urban supportive housings. The aim of this study was to document the various types and degree of risk endemic to this population. First, we describe the psychosocial characteristics of this homeless sample. Second, we compared this homeless sample with a grade-matched, high-risk, school-based sample of children (n = 146) who were identified as showing early symptoms of disruptive behaviors. Third, we compared the parents in both samples on mental health, parenting practices, and service utilization. Results showed that children living in supportive housing were in the at-risk range and had comparable levels of externalizing problems, internalizing problems, school problems and emotional strengths with the school-based risk sample receiving prevention services at a family support community agency. Mothers in supportive housing reported significantly higher psychological distress, less optimal parenting practices and greater service utilization. These findings are among the first to provide empirical support for the need to deliver prevention interventions in community sectors of care.