Neighborhoods are critical contexts for adolescent development, but little attention has been paid to how neighborhood characteristics play a role in positive youth development (PYD), notably among predominantly African American youth. This study examined distinct features of the neighborhood, including youth-serving institutional resources (YSI) and safety, as they relate to PYD among adolescents from low-income neighborhoods in an urban setting (n = 491, 68.6% African American). Because neighborhood experiences during adolescence often differ based on gender, we also examined moderation by gender. Results from cross-sectional, multilevel data suggest that neighborhood safety, YSIs, and gender are differentially associated with indicators of PYD (i.e., hope, mastery, friend support). The pattern of results suggested that when associated with mastery, YSIs may compensate for low-safety neighborhoods for adolescent females but not males. In terms of associations with friend support, YSIs may foster the development of PYD in low-safety neighborhoods for males but not females. Limitations of the current study and implications for future research are discussed.