Residential mobility and type of housing contributes to an individual’s likelihood and frequency of drug/alcohol use and committing criminal offenses. Little research has focused simultaneously on the influence of housing status on the use of drugs and criminal behavior. The present study examines how residential mobility (transitions in housing) and recent housing stability (prior 30 days) correlates with self-reported criminal activity and drug/alcohol use among a sample of 504 addicted, treatment-seeking opioid users with a history of criminal justice involvement. Findings suggest that those with a greater number of housing transitions were considerably less likely to self-report criminal activity, and criminal involvement was highest among those who were chronically homeless. Residential mobility was unassociated with days of drug and alcohol use; however, residing in regulated housing (halfway houses and homeless shelters) was associated with a decreased frequency of substance use. The finding that residing at sober-living housing facilities with regulations governing behavior (regulated housing) was associated with a lower likelihood of illicit substance use may suggest that regulated housing settings may influence behavior. Further research in this area should explore how social networks and other related variables moderate the effects of housing type and mobility on crime and substance use.