The Italian building stock faces significant challenges in energy inefficiency, with 70% of buildings nearing the end of their life cycle. Urgent interventions are required for refurbishment and technological retrofitting to enhance performance. Regulations such as the EPBD IV aim to transform existing buildings into NZEBs by 2050. This research explores innovative systems and technologies inspired by the “Energiesprong” model to enable deep retrofit interventions. The pilot project in the “Le Terrazze” district of Castelnuovo di Porto demonstrates the effectiveness of the proposed solutions, achieving substantial energy and environmental improvements while significantly reducing on-site construction activities and drastically shortening implementation timelines.