Landfill leachate is regarded as a significant point source of pollutants that may pose a hazard to the environment, particularly to surface and ground waters. Leachates are highly variable and heterogeneous. Our study was focused on the characterization of landfill leachates derived from young (YDS) and matured (MDS) dumpsites in terms of the abundance of micropollutants, antimicrobial resistance genes (ARG), and microbial community structure. The concentrations of poly- and perfluoroalkyl substances (PFASs) were found to be higher in MDS compared to YDS, i.e., 13.19 and 7.16 μg/L, respectively. Among pharmaceutical compounds, ibuprofen was detected at the highest concentrations, i.e., 12.54, 12.81, and 13.13 μg/L, in the leachates derived from MDS, YDS, and ponds. The distribution of bacteria, archaea, eukaryotes, and viruses in the three leachate samples was as follows: 85.15 ÷ 88.04%, 9.13 ÷ 12.29%, 2.20 ÷ 2.68%, and 0.12 ÷ 0.15%, respectively. In total, 31 distinct families of ARGs were identified, comprising a total of 80 ARGs. Incubation of P. putida MSCL650 in sterile leachate from the pond resulted in decreasing the minimum inhibitory concentrations for six antibiotics as compared to cells incubated in nutrient broth. Hydrological processes, i.e., runoff and infiltration, can increase the dissemination of ARGs.