Experiencing homelessness during young adulthood is associated with negative health outcomes and understanding housing trajectories of young adults experiencing homelessness may aid in the development of evidence-based public health programs designed to serve this at-risk age group. In the present study, the authors examined baseline predictors of 24-month trajectories of housing stability and unsheltered housing among a sample of 271 young adults aged 18 to 25 recruited from drop-in centers in Los Angeles. In multivariate models, the authors found that identifying as multi-racial/other and better friendship quality at baseline were associated with less steep increases in the likelihood of stable housing over time. Being employed at baseline was associated with a less steep decrease in the probability of being unsheltered over time, while illicit drug use days associated with a steeper decrease in the probability of being unsheltered over time. Continued research is needed to establish important factors determining young adults’ long-term housing trajectories in the effort to promote greater access and engagement with housing services.