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With the rapid growth of cities worldwide, there is a need to better understand factors contributing to life satisfaction in urban environments. Using data from a long-term study of the Baltimore metropolitan region, we build on existing social scientific literature to examine a suite of theoretical factors that have been proposed to explain higher life satisfaction. We find support for many previous theoretical arguments in the literature. Importantly, however, our findings reveal that these results are strikingly scale dependent. For individuals, higher incomes contribute to higher levels of satisfaction, yet social capital does not. For neighborhoods, more social capital strongly increases satisfaction, but higher incomes do not; and access to a clean natural environment always contributes to higher satisfaction, regardless of the scale of analysis. Given these findings, we conclude with the observation that future research must carefully match the “scale” of life satisfaction measurements with the explanatory variables used.