Secondary data obtained through the 2015 point-in-time homelessness count and an administrative health care utilization database was used to identify differences in demographic characteristics, health service use, and predictors of health service use among people experiencing unsheltered and sheltered homelessness. Compared to sheltered participants, unsheltered participants had higher proportions of males and Caucasians, were younger, were more likely to use any type of health service and ED services, and used significantly more of any health service and ED and outpatient services. Results also confirm that health services utilization is a complex phenomenon predicted by a variety of predisposing, enabling, and need-related factors, including mental health problems. Together, these findings demonstrate important differences between people living unsheltered and those residing in shelters and they inform local health policy and program initiatives tailored towards these homeless populations.