Guided by the recidivism reduction principle, earlier research interest in children with parents or guardians who have experienced incarceration (CPGI) relies on a risk-focused model, collapsing our understanding of these children’s lives into one dimension: their parents’ or guardians’ imprisonment. Within this landscape, the present study seeks to deepen our understanding of the inherent heterogeneity of this population while adding social context, such as neighborhood characteristics, to the mix of possible protective and risk factors to inform interventions. We examined associations between school engagement and neighborhood characteristics, grouped into built social infrastructure and social support among CPGI. These associations were then tested in three groups: CPGI with (a) at least 4 Adverse Childhood Experiences (ACEs), (b) 2–3 ACEs, including PGI, and (c) only PGI as an ACE. Results indicate that sidewalks and a higher count of neighborhood amenities are associated with increased care about doing well in school. Higher count of detracting elements is associated with increased care about doing well in school in group A. We also observed a complementary relationship between built social infrastructure and social support factors, as they are associated with care about doing well at school and completing homework differently. Social capital and living in a supportive neighborhood are associated with both increased care about school and likelihood of completing homework. Accordingly, neighborhood-based policies are recommended to meet the needs of CPGI and their families.