The objective of this investigation was to examine the associations among neighborhood conditions, neighborhood collective efficacy, family economic disadvantage, parental control behaviors, and children’s behavioral outcomes using multilevel and cross-level analyses. The proposed conceptual model incorporated propositions advanced by social disorganization theory, the structural-process model, as well as the Family Stress Model. Data were collected from a nationally representative sample of 1,337 families with children between 3 and 6 years (668 boys) drawn from 45 communities in Trinidad and Tobago. Neighborhood level indicators were assessed using census as well as parent reports whereas individual level constructs were assessed using parent reports. Findings indicated support for the Family Stress Model in that harsh punishment and parental monitoring functioned as mediators of the relationship between family economic disadvantage and behavioral difficulties (parental monitoring for prosocial behaviors). Findings from the multilevel analyses indicated that the relationship between neighborhood infrastructure deprivation and children’s behavioral difficulties and prosocial behaviors was mediated through neighborhood collective efficacy and parental harsh punishment. Cross-level interactions indicated that neighborhood collective efficacy buffered the relationship between parental discipline, monitoring, harsh discipline and behavioral difficulties. Given the importance of communities and families in influencing children’s behavioral outcomes, due consideration must be given to utilizing multilevel and cross-level perspectives both in research as well as in the development of intervention programs. Policies and programs designed to improve neighborhoods conditions, promote neighborhood collective efficacy, and advance the socioeconomic opportunities for families can help enhance the well-being of children.