Dynamic simulation tools are widely used in the workflow of energy retrofitting historic buildings as they contribute to the development of an optimised, cost-effective renovation strategy. Additionally, Building Information Modelling (BIM) applied in heritage buildings can provide a holistic platform that improves collaboration between different stakeholders involved in the management, restoration and energy-retrofit of heritage buildings, by facilitating data sharing and project coordination. However, the use of BIM for energy simulation is rarely implemented due to emerging technical complexities regarding data interoperability. In response to the above shortcomings, the paper addresses the challenges of integrating a) dynamic energy performance analysis and b) financial feasibility analysis, using Heritage-BIM (H-BIM) tools. Insights and knowledge acquired through the case of a deep renovation of a historic building in ruin condition is presented. Specifically, an integrated H-BIM approach was developed by the authors in order to propose cost-effective energy efficiency upgrade measures. The energy improvement measures concern the upgrade of the thermal transmission of the building envelope, the incorporation of efficient heating, cooling and mechanical ventilation systems, as well as the incorporation of renewable energy systems. The economic feasibility study is based on widely used financial indicators, including life cycle cost analysis (LCCA). The proposed workflow aims to become a useful methodological tool for public authorities, assisting the attraction of financing mechanisms for the restoration and energy-upgrade of the historic building stock.