Structural health monitoring is a crucial issue in areas with different hazard sources, such as Italy. Among non-invasive monitoring techniques, remote sensing provides useful information in supporting the management process and safety evaluations, reducing the impact of disturbances on the functionality of construction systems. The ground displacement time-series based on the analysis of Differential Interferometric Synthetic Aperture Radar (DInSAR) measurements, as well as the information about the geology of the area and the geometry of the construction under monitoring, provides useful data for the built environment’s structural assessment. This paper focuses on the structural monitoring and damage assessment of constructions based on the GIS integration of DInSAR measurements, geological investigation, historical surveys and 3D modeling. The methodology is applied to the residential area of Valco San Paolo in the city of Rome (Italy). Once the geological interpretation has confirmed the results of the DInSAR measurements, a quick damage assessment that considers all the possible conditions of the pre-existing damage at the time zero of the monitoring is shown for a damaged manufact in the area. The presented results highlight how the strategy to correlate the DInSAR-monitored ground settlements with the damage scales allows potentially to monitor continuous construction systems.