Each year, >1 million American children and youth experience homelessness (Hammer, Finkelhor, & Sedlak, 2002; Office of Applied Studies, 2004). The transient nature of this population makes it difficult to study, but youth homelessness has been identified with a number of problematic outcomes as well as a pathway to chronic adult homelessness (Baker Collins, 2013; Chamberlain & Johnson, 2011). Yet, few empirical studies evaluate the effectiveness of a common intervention for homeless youth—transitional housing. In this paper, we describe the outcomes of homeless youth who participated in a youth-only transitional housing program. We analyze administrative data on 174 youth who entered and exited the Daybreak Transitional Housing program (Daybreak TH) between 2011 and 2014. We find that the majority of Daybreak TH participants were employed at least 20 h a week at program exit. Youth exited Daybreak TH with higher wages on average, while nearly half achieved educational gains from program entry to exit. Youth who resided in Daybreak TH for 12 months or longer were more likely to achieve positive program outcomes than youth who entered and exited the program in fewer than 12 months. Finally, youth who used drugs and alcohol were less likely than their peers to achieve desired program outcomes, as were those who suffered from chronic illnesses or attention deficit, conduct, or disruptive behavior disorders. We conclude with a discussion of policy implications and areas for future research.