To pave the way towards buildings’ decarbonization in the context of the European Union’s (EU) policy, the methodology of cost-optimality assessment based on regulation 244/2012/EU is a useful tool to explore and foster the application of energy technologies in buildings. Meanwhile, the fostering of concentrated solar power is included in the EU solar energy strategy. In this study, the cost-optimal methodology is employed for the techno-economic assessment of the integration of a novel solar, multi-purpose energy technology, namely a parabolic trough collector-based trigeneration system, in two building types with different characteristics, namely an office and a hospital, in Greece, thus allowing the evaluation of the cost-optimal system design and the impact of the building type on the system’s techno-economic performance. Reference buildings are defined and their energy demand is calculated through dynamic energy simulations. The trigeneration system’s performance for different design scenarios is then parametrically investigated using a simulation model. For each scenario, energy, environmental and economic indicators are calculated and the cost-optimal designs are extracted. In the cost-optimal implementation, the system covered 18.19–36.39% and 3.58–15.71% of the heating and cooling demand, respectively, while the reduction of the primary energy consumption and emissions was estimated at 10–14% and 10–16%, respectively. However, differences between the buildings related to the operation schedule and the loads led to the implementation of the system being economically more attractive in the hospital, while for the office, financial support is necessary for a viable investment.