Urban sprawl is a complex phenomenon that requires a comprehensive reflection on the most significant patterns and underlying processes. While the “sprawl” notion parallels hegemonic concepts such as economic competitiveness, social cohesion, and polycentric development, an integrated analysis of sprawl patterns and processes in paradigmatic socioeconomic contexts is increasingly required to reconcile different disciplinary visions, contributing to a holistic interpretation of metropolitan change. At the same time, sprawl is an increasingly evident product of local socioeconomic contexts all over the world. A comprehensive investigation of multifaceted, form−function relationships underlying sprawl—based on a quali-quantitative analysis of representative cases—is a crucial pre-requisite of both monitoring and policy actions at multiple spatial scales, from urban/regional to national/continental levels. The present contribution proposes a contextualization of the sprawl notion in Southern Europe—a socioeconomic context characterized by compact and continuous urbanization for a long time. An integrated approach based on a visual analysis of urban and peri-urban landscapes—integrated with an extended literature survey—allows for a definition of a specific sprawl model in Southern Europe, sharing some features with the United States ideal type of sprawl and showing peculiarities with respect to common models of urban dispersion typical of Northern and Western Europe. Policies aimed at containing urban dispersion may definitely benefit from a local-based definition of sprawl, considering the specificity of form−function relationships and the underlying socioeconomic context.