The paper presents findings from a longitudinal study identifying different classes of homeless individuals in a mid-size Canadian city based on health-related characteristics and comparing the housing trajectories of these classes 2 years later. Using data collected through in-person interviews with a sample of 329 single persons who have experienced homelessness, the paper presents results of a latent class analysis. Results found four distinct latent classes characterized by different levels of severity of health problems--i.e., a class of individuals who are "Higher Functioning" (28.7%), a second class with "Substance Abuse Problems" (27.1%), a third class with "Mental Health Substance Abuse Problems" (22.6%), and a fourth class with "Complex Physical and Mental Health Problems" (21.6%) that included having diminished physical functioning, multiple chronic physical health conditions, mental health difficulties, and in some cases substance abuse problems. Follow-up interviews with 197 of these individuals (59.9%) 2 years later showed the class of individuals with substance abuse problems experiencing the greatest difficulty in exiting homelessness and achieving housing stability. Implications of these findings for social policy development and program planning are discussed.