Positive Energy Districts (PEDs) transcribe an emerging energy transition paradigm for rapid upscaling of building energy efficiency programs to match the urgency of climate mitigation and adaptation. PEDs facilitate pro-active sharing of information and experiences, responsive learning and dissemination, and cooperation across sectors and disciplines. The rapid evolution of technologies for energy efficiency and integration of renewable energy in buildings requires a research-to-design approach. Therefore, it is imperative that a designer makes informed decisions at an early stage of design from an energy-efficiency perspective. However, since PED design involves a significant number of stakeholders, the design parameters could be highly uncertain, which eventually affect the quality of the design solution space. This study uses a bilateral process workflow to quantify risks using a nonprobabilistic technique and a PED roadmap structure. The workflow evaluates different PED scenarios and quantifies the PED potential for the city of Sint-Niklaas in Belgium. The results indicate that risk quantification significantly improves PED decision-making when evaluating collective solutions (district heating) for a district.