Buildings play a central role in global decarbonization efforts, given their substantial contribution to greenhouse gas emissions throughout a building’s life cycle. To address this challenge, it is essential to minimize the environmental footprint of the construction sector through holistic assessment tools and innovative solutions. This study conducts a comparative Life Cycle Assessment (LCA) of two technological construction solutions, steel and reinforced concrete, within the context of a 14-story building refurbishment project in Pisa, Italy, with the final goal of determining the potentiality of the LCA methodology in identifying the most suitable solution in terms of sustainability and environmental impacts. Adopting a cradle-to-grave approach, the analysis examines the environmental trade-offs of these systems across 13 impact categories outlined in the Level(s) framework, using localized datasets and ISO 14040–44 methodology. The research identifies critical differences in the carbon footprint of the two solutions, with the steel frame exhibiting 23% lower carbon emissions than the concrete frame. Furthermore, the study evaluates the potential of using Recycled and Renewably Produced (RRP) steel elements to enhance sustainability further. The findings highlight the importance of integrating LCA in the early design phases to make a sustainable choice in terms of construction materials and technological solutions. By highlighting context-specific environmental impacts, this research provides actionable insights for professionals, Small and medium-sized enterprises (SMEs) and policymakers aiming to advance decarbonization efforts in the built environment.