This paper investigates the possibilities and challenges of using mass timber as a sustainable alternative for retrofitting existing buildings in Canada. To create the knowledge foundation on which to devise a holistic framework tailored to the specific characteristics of Canada's built environment, a detailed analysis of the types, geographical distribution, structural, and energy features of the local building stock is first presented. Then, previous strategies for enhancing and upgrading existing buildings with engineered timber are reviewed, classified, and evaluated. Finally, to explore economic and environmental implications, a detailed assessment of available life-cycle cost–benefit analysis approaches is conducted alongside their adaptation to Canada's building context. The findings of this paper can inform policymakers, builders, and designers in developing more sustainable building retrofit practices, design, and regulations, in line with Canada's efforts toward net zero emissions.