We examined the impact of neighborhood characteristics both directly and indirectly as mediated by parent coaching and the parent/child affective relationship on behavioral and school adjustment in a sample of urban dwelling first graders. We used structural equations modeling to assess model fit and estimate direct, indirect, and total effects of neighborhood structural and social characteristics on parenting behavior and child outcomes. Observed physical incivilities in the neighborhood were associated with lower levels of parent eliciting behavior and higher levels of child behavior problems. The effects of neighborhood structural characteristics were mediated partially through neighborhood community involvement with children, which had a direct significant impact on parent eliciting behavior and an indirect effect on child behavior problems. Neighborhood community involvement with children was associated with higher levels of parent eliciting behavior and lower levels of child behavior problems. Observed physical incivilities had a significant indirect association with poor school adjustment and a marginally significant association with positive school adjustment to first grade. Neighborhood community involvement with children was more strongly associated with positive school adjustment than poor school adjustment.