The Transit-Oriented Development (TOD) model is widely recognized as an effective urban way to integrate public transport with urban development and economic activities, promoting sustainable mobility and improving the overall quality of urban spaces. However, its adoption and implementation in Italy remain limited and fragmented. This article aims to assess to what extent and in what ways TOD principles have been adopted in the Milan Metropolitan Area, highlighting opportunities and obstacles to applying the model. Locate Triulzi, one of the Suburban Station Areas called Luoghi Urbani della Mobilità (LUM) envisaged by the Milan Metropolitan Area Plan called Piano Territoriale Metropolitano (PTM), has been selected as an emblematic case study. Here, the inclusion of Scalo Milano shopping centre has led to the achievement of the quantitative metrics envisaged for suburban TODs, but the qualitative levels of the reference model have only been partially achieved. To carry out this evaluation, a multidimensional tool based on quantitative and qualitative metrics, composed of tables and diagrams, was used. As a result of this investigation, the understanding of potential and critical issues could provide direction for local planning and, even in the absence of a strategic plan framework, guide the dynamics of spontaneous regeneration from the bottom up, providing useful design guidance for reorganizing density and public spaces in a way that is consistent with the TOD model. The research presented here confirms the need for, and provides, criteria for pursuing urban and territorial transformations that can produce cities in which walkability becomes not only a question of accessibility, but an engine for the creation of lively, safe, attractive, and ecological public spaces.