This study examined how youth's neighborhood characteristics informed their expectations of racial discrimination concurrently and longitudinally. Secondary analyses were conducted on data from Waves 1, 3, 4, 5, and 6 of the Maryland Adolescent Development in Context Study, which permitted the examination of neighborhood influences among a socioeconomically diverse sample of African American parents and adolescents (n = 863; Mage = 12.29). Youth exposed to more neighborhood disadvantage in seventh grade reported more negative concurrent neighborhood perceptions, which, in turn, predicted greater expectations of racial discrimination in eighth grade; youth's expectations remained stable into adulthood. Thus, support was found for the mediating role of youth's subjective neighborhood perceptions in the longitudinal relation between neighborhood structure and expectations of racial discrimination.