The rapid increase in construction and demolition waste (C&DW) has emerged as a significant environmental challenge, particularly due to the hazardous substances embodied within the fine residues destined into landfills. The disposal of C&DW in landfills has been widely recognized as a source of leachate, containing toxic contaminants, which pose significant environmental risks. A controlled column leaching experiment was conducted using samples with varying proportions of C&DW, gypsum, and organic content to assess their impact on leachate chemistry. The results indicate that higher C&DW content leads to increased concentrations of heavy metals, such as Pb, Hg, As, Cr, Ni, Cu, Zn, and Co, as well as other metals like Al and Fe, with peak contamination occurring within the first 13–15 weeks. Gypsum presence exacerbates heavy metal solubility by reducing pH, increasing sulfate levels, and promoting metal-sulfate complex formation. Despite remaining within regulatory thresholds, the cumulative concentration of toxic metals over time highlights potential environmental risks, particularly in landfill settings. This study underscores the need for improved C&DW management practices, enhanced waste segregation, and sustainable alternatives to gypsum to mitigate long-term ecological impacts. These findings contribute to a deeper understanding of C&DW leachate dynamics and inform policy recommendations for sustainable waste management in the construction sector.