Understanding the reasons why some areas are more attractive than others is strategic for all municipalities located in weak socio-economic contexts, which need new development opportunities to strengthen their economies and tackle the depopulation trends. Single or multiple factors can act as triggers or detractors in inner areas and fragile territories: one of these is the real estate market, which is strictly related to different social and economic issues. In order to identify adequate strategies, policies and actions, data and indicators from different sources must be jointly analysed. For this purpose, a five-phase methodological approach, based on a sequence of knowledge management operations, is proposed, so that an adequate knowledge base could support multiple analyses. Its application on the fragile of the Eporediese area (Northern Italy), consisting of 54 municipalities, led to the identification and collection of more than 35 indicators, to their organization in a GIS and finally to the utilization of this preliminary knowledge base for analytical purposes. Different statistical analyses were performed and interesting results achieved on the existing relationships between real estate market variables, the presence of urban services and the main characteristics of the population. In particular, property listing prices and the advertisements frequency emerged as key factors to be jointly considered with social vulnerability aspects. Moreover, results pointed out other interesting variables, such as the Digital Transformation Indicator and the Urban Development Indicator, to be further explored in future research developments. Also the current version of the GIS has to be further tested and extended by selecting and adding more variables and data from other data sources, with the aim of properly support local authorities, scholars and study centres in identifying, collecting, organising, using and sharing multi- level data.