Using data from the National Longitudinal Survey of Youth merged mother-child file, this article examines the relationship between living in four different family structures on key measures of youth well-being, studied separately by race. The authors also examine whether contextual factors mediate these associations. For Black youth, we find no effects of family structure on youth well-being; however, community context measures are associated with youth outcomes. For White youth, single parenthood and cohabitation are associated with poorer youth outcomes; however, in some cases, these associations are mediated with the inclusion of the community context measures. (Contains 3 tables.)