BIPV (building-integrated photovoltaics) technologies may play a key role in the transition towards low-carbon energy communities. A relevant aspect to consider to correctly assessing the techno-economic and environmental performance of BIPV applications is the dynamic variation of the climate boundaries conditions during the entire systems’ lifespan. This study provides an innovative approach to optimize BIPV applications in the early design phase. By using a real case study, that consists of four residential buildings, located in Milan, Italy, including about 142 residential units, simulations have been run with two different weather datasets, one representative of the current weather conditions and one representative of their projection in 2050, to investigate the possible impacts of climate change on some relevant key performance indicators (KPIs), with a particular focus on the minimization of the levelized cost of electricity (LCOE). This approach is meant to foster a more accurate design of BIPV systems in urban contexts. Results show that the LCOE decreases by almost 50% from 2020 to 2050 optimizations, and the self-sufficiency target is guaranteed with a smaller installed PV capacity.