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There are growing concerns about substantial socio-economic differences between districts as well as gender achievement gaps in many developed nations. Yet limited attention has been given to how district contexts shape student educational outcomes across genders. Moreover, prior estimates may be influenced by unmeasured differences between districts. In this study, we exploit the within-district variation across six years in a multilevel framework to improve our current understanding of contextual factors in student educational development. Our findings, based on nationally representative Seoul Educational Longitudinal Study linked to Seoul Survey (2012 to 2017), show that boys benefit from district with higher levels of cultural satisfaction and social trust, beyond individual and school-level factors.