Along the roadmap to a Sustainable Real Estate-Scape, energy retrofit campaigns on wide city compartments represent a pivotal task, where the importance of the collaboration between the public and private sectors is crucial. Energy retrofit programs on building assets are subject to multiple uncertainty factors (e.g., climate, energy-economy forecasts, etc.) that act as a primary barrier to investment in this field. This paper aims to discuss risk management techniques to understand better how to deal with this kind of uncertainty. The research specifically addresses the techniques of sensitivity analysis and Monte Carlo simulation, focusing first on the phase of variables selection and their probability definition, including climatic, environmental, energy, economic, financial, and stochastic parameters. In this article, it is suggested to include correlation coefficients in the input variables of risk analysis, preferring the two-dimension Monte Carlo simulation to its simple version, since the results are more reliable when separating aleatory from epistemic uncertainty; thus, the results are more reliable. Moreover, it is seen how a sensitivity analysis based on percentile variations of the inputs provides a more accurate representation of risk if compared to the most common sensitivity analysis based on percentage deviations of the inputs. Conducting a sensitivity analysis using percentile variations gives realistic and reliable results, reflecting the tailored definition of uncertainty around the inputs on the basis of specific market analyses or historical series.