The regeneration of industrial railway yards represents a unique opportunity to address urban challenges where ecological connectivity, cultural heritage, and multifunctional public spaces intersect. Milan’s ongoing railway yard regeneration project, encompassing sites like Porta Romana, Farini, and Greco-Breda, offers a compelling framework to explore how these post-industrial spaces can be reimagined through integrative design strategies. This paper investigates how railway yards and their residual architectural heritage can be transformed into vibrant urban assets. Using a comparative analysis of different regeneration sites, the study identifies key strategies, including ecological corridor integration, adaptive reuse of historical structures, and the creation of multifunctional public spaces. These approaches highlight the potential of railway yards to act as catalysts for ecological resilience, cultural continuity, and urban vitality. Particular emphasis is placed on ecological corridors’ role in reconnecting fragmented urban landscapes and on adaptive reuse as a means of preserving cultural narratives while meeting contemporary urban needs. The multifunctional design of public spaces not only addresses diverse community demands but also fosters social inclusion and environmental adaptation, enhancing the value of these former industrial areas. By adopting a cross-disciplinary perspective that integrates ecological, cultural, and urban design dimensions, this research contributes to filling a critical gap in the literature. It situates Milan’s railway yard regeneration as a model for post-industrial cities seeking to redefine residual spaces and heritage within the urban fabric. The findings provide actionable insights into leveraging industrial heritage for sustainable, inclusive, and resilient urban development.