Abstract Despite the global call for a paradigm shift towards new environmentally conscious urban planning, little has changed in practice, especially in hot climatic regions. This paper helps bridge this gap by introducing an automated parametric workflow for performance driven urban design. The methodology was tested here in the climatic and urban Mediterranean context consists of a parametric typological analysis, automated through Grasshopper with a total of 1920 iterations. For each iteration the performative effects of both building (i.e. typology, window to wall ratio and glazing properties) and urban design parameters (i.e. distance between buildings, floor area ratio and the orientation) were evaluated for residential and office building uses. The performance metrics - monthly/hourly energy load match and spatial daylight autonomy - were calculated using Energyplus and Radiance, respectively, and recorded for each iteration. The main results indicate substantial performative differences between typologies under different design and density scenarios; the correlation between the shape factor and the energy load match index as well as the benefits of the courtyard typology in terms of energy balance, with its challenging daylight performance, were established. These results demonstrate the potential of this workflow to highlight the design trade-offs between form and environmental performance considerations by designers and thus provide a new way to bridge the performative gap between buildings and their urban surroundings. Its application should help designers and policy makers contextualize nearly zero energy block concepts as well as define new criteria and goals.