Nowadays, construction and demolition waste management has become a critical process for the construction industry, as the specific waste stream poses important environmental issues and challenges. In the case of dismantling end-of-life buildings, the selection of the appropriate technique between deconstruction and conventional demolition is a critical decision affecting the total volume and type of produced waste. Toward this effect, in this paper, a novel decision-making model for the optimization of end-of-life buildings’ deconstruction and demolition processes is proposed. The objective of the proposed model is the simultaneous and weighted optimization of the total cost and time for the completion of the deconstruction and demolition processes, taking into consideration economic, legislative, and environmental criteria. Finally, a demonstration of the application of the proposed model is presented via two specific case studies and by discussing a few interesting managerial insights.