In recent years, space-borne InSAR (interferometric synthetic aperture radar) techniques have shown their capabilities to provide precise measurements of Earth surface displacements for monitoring natural processes. Landslides threaten human lives and structures, especially in urbanized areas, where the density of elements at risk sensitive to ground movements is high. The methodology described in this paper aims at detecting terrain motions and building deformations at the local scale, by means of satellite radar data combined with in situ validation campaigns. The proposed approach consists of deriving maximum settlement directions of the investigated buildings from displacement data revealed by radar measurements and then in the cross-comparison of these values with background geological data, constructive features and on-field evidence. This validation permits better understanding whether or not the detected movements correspond to visible and effective damages to buildings. The method has been applied to the southwestern sector of Volterra (Tuscany region, Italy), which is a landslide-affected and partially urbanized area, through the use of COSMO-SkyMed satellite images as input data. Moreover, we discuss issues and possible misinterpretations when dealing with PSI (Persistent Scatterer Interferometry) data referring to single manufactures and the consequent difficulty of attributing the motion rate to ground displacements, rather than to structural failures.