This chapter investigates a model to integrate performance measure and urban design in the context of a high-density urban environment. The objective of this research is to discuss how performance-based modeling can be used for addressing problems of energy self-sufficiency and thermal comfort in a vertical and complex urban environment, in which increasing density may cause climate and ecological consequences. An urban neighborhood in Misono of Tokyo’s metropolitan region is studied to test the relationship between vertical urban form and energy performance. Benchmarking the performance behind urban form and neighborhood typologies leads to criteria of high performance and low carbon emission. The chapter discusses the policy implications of performance-based urban design and development in the context of the Misono Smart City Project, a site for Tokyo’s 2020 Olympics, and proposes a transformative approach to generate better performance for an energy resilient and sustainable urban future.