The ambitious target of decarbonization requires a deep transformation of the construction sector and a systematic renovation of the existing building stock. Such a transition requires the adoption of new technologies conceived with a Life Cycle Thinking approach and implementing digital tools, maximizing performances, while enabling reduction of impacts and costs along the building life cycle. In the paper, a wooden construction technology for the deep renovation of existing buildings is presented. The solution is prefabricated off-site, made of a renewable bio-based material, and adopts innovative dry, standardized connections, enabling concentrating damage in case of earthquakes. The system is applied from the outside, without relocating inhabitants, that might otherwise hinder the renovation. An additional CLT engineered shell, coupled with an optimized thermal layer and new plants along the building perimeters, allow the combined energy and structural upgrade of the building. Finally, specific sensors are added for the continuous monitoring of structural health and environmental parameters. The proposed solution was developed within an industrial project integrating academic research and industrial leading-edge technologies and was applied to a typical post-WWII masonry building.