In the present work, both unused plasticized poly(1-chloroethylene) membranes and membranes taken from a flat roof area were comprehensively analysed. First, tensile strength and elongation at breaking points were determined, followed by measurements of wettability. Secondly, morphological changes were analysed using scanning electron microscopy (SEM). To study chemical changes in aged membranes, Fourier transform infrared spectroscopy (FTIR) analysis in the attenuated total reflection mode (ATR) was used. Finally, thermogravimetric analysis and differential scanning calorimetry (TGA-DSC) were performed simultaneously to study thermal degradation. The results show obvious changes in the mechanical, physical and chemical properties of membranes caused by plasticizer loss. Surface microstructure becomes stiffer, which leads to contractions and the prevalence of voids. In cross-sectional area, average thickness values decrease. Due to the degradation of the plasticized waterproofing membranes, the roofing area had to be completely replaced.