Residential mobility is one documented stressor contributing to higher delinquency and worse educational outcomes. Sensitive period life course models suggest that certain developmental stages make individuals more susceptible to the effects of an exposure, like residential mobility, on outcomes. However, most prior research is observational, and has not examined heterogeneity across age or gender that may inform sensitive periods, even though it may have important implications for the etiology of adolescent development. Moreover, there are important translational implications for identifying the groups most vulnerable to residential mobility to inform how to buffer adverse effects of moving. In this study, low-income families were randomized to residential mobility out of public housing into lower poverty neighborhoods using a rental subsidy voucher (“experimental voucher condition”), and were compared to control families remaining in public housing. The sample was comprised of 2829 youth (51% female; 62% Non-Hispanic Black, 31% Hispanic, 7% other race). At baseline, youth ranged from 5 to 16 years old. This study hypothesized that random assignment to the housing voucher condition would generate harmful effects on delinquency and educational problems, compared to the control group, among boys who were older at baseline. The results confirmed this hypothesis: random assignment to the experimental voucher condition generating residential mobility caused higher delinquency among boys who were 13–16 years old at baseline, compared to same-age, in-place public housing controls. However, residential mobility did not affect delinquency among girls regardless of age, or among boys who were 5–12 years old at baseline. The pattern of results for educational problems was similar but weaker. Families with teenage boys are particularly vulnerable to residential transitions. Incorporating additional supports into housing programs may help low-income, urban families to successfully transition to lower poverty neighborhoods.