The management and the safeguard of existing buildings and infrastructures are actual tasks for structural engineering. Non-invasive structural monitoring techniques can provide useful information for supporting the management process and the safety evaluation, reducing at once the impact of disturbances on the structure’s functionality. This paper focuses on the exploitation of advanced multi-temporal differential synthetic aperture radar interferometry (DInSAR) products for the structural monitoring of buildings and infrastructures, subjected to different external actions. In this framework, a methodological approach is proposed, based on the integration of DInSAR measurements with historical sources, accurate 3D modelling and consistent positioning of the reflecting targets in the GIS environment. Documentary sources can prove particularly helpful in collecting technical information, to reconstruct an accurate 3D geometry of the building under monitoring, limiting in-situ surveys. The analysis of DInSAR-based displacements time series and mean deformation velocity values allows the identification of possible critical situations for buildings to be monitored. The paper presents different approaches, with increasing accuracy levels, to study the active deformative processes of the examined buildings and the related damage assessment. An insight into these interpretative approaches is given through the application of the proposed procedure to two case studies in the city of Rome (Italy), the residential building named Torri Stellari in Valco San Paolo (1951–1953) and the housing complex referred to as Corviale (1967–1983), by exploiting the whole COSMO-SkyMed data archive (both ascending and descending acquisitions), collected during the 2011–2019 time interval. Pros and cons of the various approaches are deeply discussed, together with an estimation of the required computational effort.