Previous urban sprawl studies have typically taken a cross-sectional approach without examining how sprawling urban areas are performing over time. Longitudinal studies of individual or household travel behavior and built-environment preference have made some progress in this direction, but very few studies have explored the longitudinal interaction of urban form with transportation and environmental outcomes. This study begins to fill this gap by evaluating the transportation and environmental impact dynamics of several key dimensions of urban sprawl: density, land use mix, centrality, and street connectivity. The central hypothesis is that while the built environment is durable and development patterns change slowly, the impacts of urban sprawl are dynamic rather than static and are accelerated in more sprawling cities relative to less sprawling cities. To test this hypothesis, a panel dataset of 7 years (2000–2007) was developed for 60 Metropolitan Statistical Areas of the US and a hybrid modeling framework that incorporates fixed and random effects is applied to evaluate different transportation and environmental outcomes over time. We found that the influence of urban centrality or the strength of urban sub-centers on the travel pattern of commuters and transit users is dynamic. This suggests that people living in cities with stronger centers drive less and use public transportation more over time. For environmental outcomes, we found that cities with higher density have experienced a significant decrease in ambient ozone and PM2.5 concentrations after controlling city-specific variables.