The Modena Automotive Smart Area (MASA) is an experimental project, based on a public-private partnership, aiming at the development of an urban living lab to test, evaluate, and implement connected and autonomous vehicles. It is proposed as a case study that contains all the key elements to convey scalability, replicability, and operational flexibility. MASA is an example of public-private partnership with the Municipality of Modena and the University of Modena and Reggio Emilia, strengthened by the endorsement of the Italian Ministry of Infrastructures and Transport and the support of the Emilia-Romagna Region, also involving industrial partners, in the implementation of a triple helix model. The research and experimentation activities concern interactions between vehicles, between vehicle and moving obstacle, between vehicle and city. The present contribution discusses the impact on the complexity of the urban environment both as digital and physical transformations and the possibility of a scalable model from a district area to an urban network.