To achieve global sustainable development goals, implementing renewables and increasing electrification in different sectors, especially heating and cooling, should be paramount. However, the full electrification of these systems can cause extra stress on the electrical grid. On-site generation and utilization of efficient systems like heat pumps are viable options to facilitate decarbonization and achieve sustainable development goals. This study introduces a set of automated workflows for retrofitting energy systems with renewable and efficient systems. These workflows are parts of the developing urban simulation platform, TOOLS4Cities, a flexible, data-driven urban simulation platform that enables the automated techno-economic assessment of energy retrofits in urban areas by integrating detailed energy demand simulations with life cycle cost analysis. Its object-oriented structure and standardized data models allow it to adapt to different regions by incorporating location-specific building archetypes, energy systems, and climatic conditions. The urban building energy modelling workflow along-side PV and heat pump modelling workflows was implemented to assess the techno-economic performance of PV-integrated heat pump systems in two distinct climates: Palma in Mallorca, Spain, and Montréal in Canada. A residential district in Palma, Mallorca, was analyzed, and using features of the developed tool, the same district was modelled under the different climatic conditions of Montreal. The building energy demands, consumption, and on-site generation in selected climates are compared. Palma’s higher solar potential supported greater self-sufficiency at lower costs, while Montréal’s colder climate and higher heating demands increased LCC for similar self-sufficiency levels.