Accessibility and urban walkability are the cornerstones of urban policies for the contemporary city, which needs to be oriented towards sustainable development principles and models. Such aims are included in the objectives of the 2030 Agenda, as well as in the ambitious objectives of the ‘European Green Deal’. These concepts are closely linked to the paradigm of a sustainable city—livable, healthy and inclusive—based on a system of high-quality public spaces and on a network of services and infrastructures, both tangible and intangible, capable of strengthening and building new social, economic and environmental relationships. It is necessary to recognize potential opportunities for connection and permeability in consolidated urban environments. These are very often fragmented and are characterized by enclaves of very different kinds. Ghettoes and gated communities, old industrial plants and military installations and facilities, to cite a few, represent examples of cases where closures on urban fabrics are realized, impeding full walkability and accessibility. Within such a framework, the present research is aimed at focusing on a particular set of enclaves, such as those represented by the military sites being reconfigured to civilian use, a phenomenon that characterizes many urban areas in the world; in Europe; and in Italy, in particular, given the recent history and the Cold War infrastructure heritage. In such a sense, the city of Cagliari (Sardinia Island, Italy) represents an interesting case study as it is characterized by the presence of a series of military complexes; real ‘enclaves’ influencing the proximity connections; and, more generally, walkability. Building on previous research and analysis of policies and projects aimed at reintroducing, even partially, this military asset into civilian life (Green Barracks Project (GBP)-2019), this paper proposes and applies a methodology to evaluate the effects of urban regeneration on walkability in a flexible network logic, oriented to the ‘15 min city’ model or, more generally, to the renewed, inclusive, safe “city of proximity”, resilient and sustainable.