Urban planners are often challenged with the task of developing design solutions which must meet multiple, and often contradictory, criteria. In this paper, we investigated the trade-offs between social, psychological, and energy potential of the fundamental elements of urban form: the street network and the building massing. Since formal methods to evaluate urban form from the psychological and social point of view are not readily available, we developed a methodological framework to quantify these criteria as the first contribution in this paper. To evaluate the psychological potential, we conducted a three-tiered empirical study starting from real world environments and then abstracting them to virtual environments. In each context, the implicit (physiological) response and explicit (subjective) response of pedestrians were measured. To quantify the social potential, we developed a street network centrality-based measure of social accessibility. For the energy potential, we created an energy model to analyze the impact of pure geometric form on the energy demand of the building stock. The second contribution of this work is a method to identify distinct clusters of urban form and, for each, explore the trade-offs between the select design criteria. We applied this method to two case studies identifying nine types of urban form and their respective potential trade-offs, which are directly applicable for the assessment of strategic decisions regarding urban form during the early planning stages.