Landslides are one of the most relevant geohazards worldwide, causing direct and indirect costs and fatalities. Italy is one of the countries most affected by mass movements, and the Molise region, southern Italy, is known to be susceptible to erosional processes and landslides. In January 2003, a landslide in the municipality of Agnone, in the Colle Lapponi-Piano Ovetta (CL-PO) territory, occurred causing substantial damage to both structures and civil infrastructure. To investigate the evolution of the landslide-affected catchment over approximately one century, different data were taken into account: (i) literature information at the beginning of the twentieth century; (ii) historical sets of aerial optical photographs to analyse the geomorphological evolution from 1945 to 2003; (iii) SAR (Synthetic Aperture Radar) data from the ERS1/2, ENVISAT and COSMO-SkyMed satellites to monitor the displacement from 1992 to 2015; (iv) traditional measurements carried out through geological and geomorphological surveys, inclinometers and GPS campaigns to characterize the geological setting of the area; and (v) recent optical photographs of the catchment area to determine the enlargement of the landslide. Using the structure from motion technique, a 3D reconstruction of each set of historical aerial photographs was made to investigate the geomorphological evolution and to trace the boundary of the mass movements. As a result, the combination of multitemporal and multitechnique analysis of the evolution of the CL-PO landslide enabled an assessment of the landslide expansion, which resulted in a maximum length of up to approximately 1500 m. A complete investigation of the past and present deformational sequences of the area was performed to potentially plan further mitigation and prevention strategies to avoid possible reactivations.