Shortened sleep duration in adolescence has been found to be associated with adverse health outcomes. While several studies have explored individual predictors, few have examined the role of neighborhood-level factors, family, and peer contexts as predictors of sleep among adolescents. We examined contextual factors of sleep duration in a sample of 1,614 urban, public high school students from the 2008 Boston Youth Survey. Neighborhood data came from the 2008 Boston Neighborhood Survey of 1,710 adult Boston residents, the 2009 American Community Survey Census (ACS), and Boston Police. Using multilevel linear regression, adjusting for neighborhood and school clustering, age, race, and sex, we found concentrated neighborhood poverty to be positively associated with sleep duration (β = 0.09, p = .03). Family context was significantly associated with longer sleep duration: >1-3 hr of homework per night reported longer sleep compared with students reporting ≤1 hr per night (β = 0.20, p = .005). Students reporting lower levels of positive parenting influence had shorter sleep duration (0-25th percentile: β = -0.25, p = .01; 26th-50th β = -0.24, p = .03), compared with students in the highest percentile. Students who never ate dinner with family had shorter sleep duration as compared with those having dinner with family 5 or more times per week (β = -0.22, p = .05). Our findings focusing on neighborhood and family context represent potentially modifiable practices. These finding are important for public health advocates and health care providers as they seek to curb the epidemic of sleep deprivation in youth. (PsycINFO Database Record (c) 2018 APA, all rights reserved).