This research concerns the issue of landscape risk due to the progressive spread of construction in rural areas through the creation of a “site-specific” analysis and evaluation model and its application to the context of the municipal area of Noto (Italy). The phenomenon of construction in rural areas was facilitated by the regulatory evolution of the Sicilian Region, which supported the construction of artifacts in agricultural areas to boost cultivation and production, but which, for the most part, was intended for seasonal residential use. In particular, the municipal territory of Noto is characterized by remarkable landscape values, including very low building density, large portions of the territory remaining almost uncontaminated, and the widespread presence of cultural and ethno-anthropological assets. Consequently, the demand for localization in rural areas, now also driven by the tendency to decongest dense urban areas in order to contain the effects of the pandemic, is a phenomenon that must be countered, on the one hand, and addressed and regulated on the other. The objective of this study is to provide the local administration with a planning tool to determine permissible interventions in various areas of the landscape context. This has guided the process of representing the phenomenon in quantitative and spatial terms, and of evaluating the territory targeted. A large set of data, coordinated in a hierarchical set of indices by means of a multidimensional valuation approach, allows us to provide an orderly and robust representation of the resilience of the landscape at risk from building pressure while considering multiple perspectives.