Research on contextual and neighborhood effects has grown exponentially over the past decade as researchers have reacknowledged that community matters. Although empirical findings have consistently documented the significant influence of neighborhood context, the field is just beginning to investigate the varied and multiple pathways through which this influence is transmitted. The current study found support for both a direct and indirect influence of perceived neighborhood structural characteristics (i.e., neighborhood stability, income), measured at the block level, on neighborhood and youth outcomes. Directly, perceived neighborhood advantage led to significantly lower neighborhood rates of official delinquency and higher rates of prosocial activity. Indirectly, perceived neighborhood advantage significantly impacted outcomes by influencing more proximal constructs such as community social organization, informal social control, parenting practices, and affiliation with delinquent peers. Different pathways were significant across neighborhood and youth outcomes, yet perceived neighborhood advantage, in particular neighborhood stability, consistently exerted substantial effects, highlighting the need for more comprehensive and multilevel prevention efforts.