The energy-saving potential of heat pump technology is widely recognized in the building sector. In retrofit applications, especially in old and historic buildings, it may be difficult to replace the existing distribution and high-temperature emission systems. Often, historical buildings, especially the listed ones, cannot be thermally insulated; this leads to high temperatures of the heat carrier fluid for heating. In these cases, the main limits are related, on the one hand, to the reaching of the required temperatures, and on the other hand, to the obtaining of good performance even at high temperatures. To address these problems, a suitable solution can be a two-stage heat pump. In this work, a novel concept of a two-stage heat pump is proposed, based on a transcritical cycle that uses the natural fluid R744 (carbon dioxide) with an ejector system. The second refrigerant present in the heat pump and used for the high-temperature stage is the R1234ze, which is an HFO (hydrofluoro-olefin) fluid. This work aims to present the effective energy performance based on real data obtained in operating conditions in a monitoring campaign. The heat pump prototype used in this application is part of the H2020 Cheap-GSHP project, which was concluded in 2019.