Since the requalification of the existing building stock has become a priority in the last years, many national incentives have been allocated. A deep and systematic integrated approach to the built environment while pursuing sustainability, safety, and resilience at the same time is the only way to avoid such relevant economic effort will be a missed chance. However, adopting an integrated approach is not enough if Life Cycle Thinking (LCT) principles are not considered. A LCT perspective not only may affect the material to be used for the retrofit, but it undermines the usual modus operandi right from the preliminary design phase of the intervention; for example, the structural details of the strengthening solution must be conceived to be easily off-site prefabricated, transported and assembled, and demounted and re-assembled in a different way at the end of life. In this paper, different iso-performance strengthening solutions are developed and compared through the application on a reference case and considering the whole life cycle of the retrofitted building. All the structural solutions considered were then coupled to the same energy recovery intervention, which makes it possible to pass from an energy class E to a class A1.