This investigation examined the relationships between middle school-aged children’s perceptions of their social environments (home, school, neighborhood, and parental work) with self-reports of well-being. In the present study, well-being was defined by measures of physical health and psychological happiness. Data from the Nurturing Families Study were collected during in-person interviews with adolescents in dual-earner and single working parent families. Adolescents’ subjective assessments were analyzed through two hierarchical regression models: mothers’ (N = 149) and fathers’ (N = 150). Findings suggest that child gender, perceptions of the school environment, and parents coming home from work in a good mood significantly predict the variability in adolescent self-reports of well-being. The school environment was found to have the strongest predictive power over variations in adolescents’ well-being. Implications for practice and research, including improving supports within schools and focusing more attention on parental mood after work, are discussed.