The present study investigates the reactivation of a paleolandslide due to the expansion of a community in an area covered by plastic Pliocene marls in the southwestern part of Cyprus. The landslide, which takes place in an area with gently sloping ground and relatively shallow water table, affects more than 100 residential buildings. In the context of the study, building damages and ground surface ruptures were mapped through field work campaigns. Remote sensing data from InSAR (Interferometric Synthetic Aperture Radar) analysis were evaluated in conjunction with available geological, geotechnical and hydrogeological data. Subsequently, the landslide was backanalyzed using the finite element method to examine possible failure mechanism scenarios and shed light on the influence of potential triggering factors. The results indicate that the paleolandslide has been almost fully reactivated, with the main cause of the reactivation being the rising of the phreatic water table due to long-term discharges of wastewater through the absorption pits of the residential developments. The water table rise was further amplified by rainwater infiltration during rainy years. According to the backanalysis results, the slip surface follows the bedding planes of weak marl horizons with residual friction angle of the order of 10°.