Understanding the resilience of urban forms as a latent force that drives a place’s physical characterization and social cohesion is essential for defining successful adaptive processes of pre-existing urban fabrics. Budapest’s ninth district (Ferencváros) is an outstanding example of transforming a complex historical urban context, which underwent renovation strategies guided by maintaining and enhancing essential morphological elements. Courtyards have great relevance in conditioning the well-being in areas of high occupational density, especially in terms of accessibility to urban green infrastructure. In the case of Ferencváros, they were reframed to add new layers of use and to improve territorial integration by unifying smaller private courtyard unities into more extensive communal areas, creating a comprehensive urban green network, preserving urban heritage, and increasing green coverage. This study assesses how this recent re-urbanization phenomenon is related to political changes in a post-socialist city. The conjuncture found in Ferencváros is unique, yet it can be applied in other similar contexts. The methodology applied to this study is supervised classification for the quantitative analysis of remote-sensing image data with GIS software assistance—a procedure rarely applied in medium-scale urban analysis. However, it was verified to be precise and effective in tracking morphological changes. The preliminary results indicate a significant intensification in greenery in the urban pattern, especially in the core areas of the blocks: the courtyards. After the intervention, green areas became more predominant, cohesive, and articulated.