This study used community contextual variables to investigate adolescent academic achievement, examining school districts and individual schools with 8th grade students. The first analyses were conducted for school year 1997-98. The school district model was replicated for 1996-97. Data came from the Department of Health and Human Services, Bureau of the Census, and Virginia Departments of Education and Health and Human Services. The study employed community social disorganization theory to explain variations in academic achievement as measured by standardized tests. It utilized structural equation modeling to reduce biased parameter estimates and investigate relationships between community contextual variables and determine whether contextual variables influenced academic achievement. The first structural equation model of the school district for 1997-98 accounted for 68 percent of the variance in adolescent academic achievement. When replicating the model for 1996-97, it accounted for 75 percent of the variance in academic achievement. When contextual variables at the school level were modeled, 65 percent of the variance was accounted for. Community social disorientation theory explained a significant amount of variance in academic achievement. The strongest variable throughout the analyses was student eligibility for free and reduced lunch, at both the school and district level. (Contains 31 references.) (SM)