Background: Homelessness is associated with health problems and with adverse childhood experiences (ACEs). The risk of chronic health conditions for homeless compared to housed youth, and how this risk interacts with ACEs remains unclear. This study investigated the relationship between ACEs, housing, and child health, and whether: 1) ACEs and health vary by housing context; 2) ACEs and homelessness confer independent health risks; and 3) ACEs interact with housing with regard to adolescent health. Methods: Using data from 119,254 8th–11th graders, we tested independent and joint effects of ACEs and past year housing status (housed, family homelessness, unaccompanied homelessness) on overall health and chronic health conditions, controlling for sociodemographic covariates. Results: The prevalence of ACEs varied by housing status, with 34.1% of housed youth experiencing ≥1 ACE vs. 56.3% of family-homeless and 85.5% of unaccompanied-homeless youth. Health status varied similarly. Homelessness and ACEs were independently associated with low overall health and chronic health conditions, after adjusting for covariates. Compared to housed youth, both family-homeless youth and unaccompanied-homeless youth had increased odds of low overall health and chronic physical and/or mental health conditions. All ACE x housing-status interactions were significant (all p < 0.001), such that ACE-related health risks were moderated by housing status. Conclusions: ACEs and housing status independently predict health status during adolescence beyond other sociodemographic risks. Experiencing homelessness, whether unaccompanied or with family, is associated with increased health risk, and every additional ACE increases this risk. Clinicians and health systems should advocate for policies that include stable housing as a protective factor.