High school students with a disability often experience social isolation and exclusion. Previous research has not explored the extent to which youth with a disability feel connected to their school environment, their sense of school community. This study utilized data from The National Longitudinal Transition Study-2 (NLTS-2), a 10-year longitudinal dataset that includes high school students with various disabilities. The study proposed a theoretical framework for sense of school community through maximized school assets and minimized school challenges. The study sample included a total of 1,180 high school students, 11th (n = 443) and 12th (n = 737) graders who completed surveys. Multiple linear regression analysis revealed that a combination of school assets and school challenges of high school experience predicted sense of school community among 11th and 12th graders. Practical implications for increasing sense of school community and reducing social isolation are discussed.