Within the scientific debate on urban regeneration, this paper intends to question possible planning techniques to address the implementation of widespread regeneration interventions in obsolete residential areas within medium-sized European cities, with particular attention to constructing a cognitive framework to locate redevelopment interventions. The widespread urban regeneration approach has yet to be sufficiently explored in the scientific literature, which focuses much more on replacing large derelict areas, though it seems particularly relevant for research and urban practice. This paper aims to illustrate a methodological framework for defining obsolete and degraded areas (at the block scale) suitable for redevelopment. Various criteria are considered, e.g., land use, buildings’ dating, state of preservation, population density, public spaces, and facility provision, and degree of accessibility. The methodological framework is then tested in the medium-sized Italian city of Parma. Data set parameters and threshold values to quantify the previously introduced criteria and perform GIS-based statistical and spatial analysis. The results show 96 areas potentially in need of regeneration, providing an opportunity to reflect on the criteria of suitability and priority for transformation and the framework of past and future planning scenarios.