The residential building stock represents one of the major players in energy use and greenhouse gas emissions; thus, it is fundamental to reduce the energy used. Simulation tools are becoming more and more accurate in compliance with the new requirements both at the single-building and at the district scale, although they are not affordable by non-specialist users such as policymakers. The research concerns the evaluation of the energy demand for space heating for a historical district that is representative of the Italian building stock. The work compares dynamic and specialist-oriented urban scale tools such as Energy Urban Resistance Capacitance Approach (EUReCA) and City Energy Analyst (CEA)) as well as a quasi-steady-state calculation method (Excel spreadsheet), which is more affordable for non-specialist users. The work was carried out to assess the possible deviation of the results between the dynamic and quasi-steady-state calculation methods, as well as to identify any limits and opportunities in the application of the latter procedure, which is currently the official national calculation tool for the implementation of Directive 2010/31/EU. The study shows how the quasi-steady-state method predicts a reliable building energy demand, in line with the results obtained by the two dynamic tools, when considering only geometry and infiltrations as input. However, the limits of the quasi-steady-state method emerge when introducing internal loads, significantly underestimating the energy demand compared to CEA and EUReCA simulations. The results underline the potential application of the quasi-steady-state method to predict energy demand, although dynamics tools are more reliable but far more complex. Major findings through two methods concern the impact of solar heat gains on the overall heating demand at both the single building and the district scale. The different results between the tools provided evidence of a gap in the use of the simplest tool and demonstrated the accuracy and reliability of the proposed approach with a lower computational effort.