According to the last census of 2019, about two million Italian buildings are more than 100 years old. Building energy retrofitting involves a diverse mix of influencing factors, depending on history, intended use, and construction techniques. This paper aims to assess the energy needs of a historic building by evaluating the variability of climatic conditions and internal loads, as well as the thermal capacity of the building envelope. The energy analysis was conducted using dynamic simulation systems (TRNSYS). The purpose of the study is to provide an analysis of the current energy conditions of the building to identify the main critical issues and suggest the most suitable interventions to be implemented. All the transformations were conducted to meet the nZEB requirements and evaluate technical and economic feasibility, compatibility with architectural and landscape constraints, and large-scale replicability. Specifically, to reach the proposed targets, a 36 kWp PV system was implemented for an area of 210 m2, in addition to the Air Handling Unit (AHU) already present. The profit index is above the unit, and it yields a time range between three and four years. Therefore, fully respecting the energy performance parameters required by the Italian legislation, the study demonstrated the unattainability of the nZEB class for a listed building.