The present study used data from 132 families that were homeless and a comparison group of 434 housed families in order to compare family functioning across the two groups. Family functioning was assessed by family support workers when the families sought help from one of seven family service agencies in Washington, DC. Multiple regression models showed that there were few differences between homeless and housed families; a difference that did emerge showed that homeless families fared better than housed families in terms of children's developmental stimulation. However, when considering the compounding effects of additional family risk factors, adverse effects of homelessness were observed. As compared with housed families, homeless families with a history of parental mental illness had limited access to support networks and poorer interactions with their children. Poor financial and living conditions were observed among homeless families with histories of substance use. Policy implications and directions for future research are discussed.