A number of models have been proposed to explain the relationship between family structure and adolescent problem behaviors, including several that consider parent-child relations, family income, stress, and residential mobility. However, studies have not explored whether the different types of communities within which families reside affect the association between family structure and problem behaviors. A community context model also suggests that the relationship between family structure and problem behaviors may be conditioned by community characteristics. The results of a multilevel regression model that used data from the National Educational Longitudinal Study (NELS; n = 10,286) indicated that adolescents from homes with a recently divorced mother, a mother and stepfather, a single mother, or a single father reported more problem behaviors regardless of the community context. Moreover, adolescents living in communities with a high proportion of impoverished residents, female headed households, or jobless males reported more problem behaviors irrespective of family structure.