As sustainability becomes a central concern in construction, the industry witnesses a significant surge in the adoption of material circularity principles, reflecting a new approach to resource management. Although mass timber construction holds significant potential for end-of-life (EoL) material circularity due to its natural materials and prefabrication, conventional connection systems hinder material reuse. Integrating interlocking techniques into modular construction could enhance circularity and enable future autonomous construction. This paper summarises design-for-reuse (DfR) strategies focusing on connection design for rapid assembly and disassembly of Cross-Laminated Timber (CLT) modules. These strategies can promote innovative connections with enhanced material circularity, which were illustrated through a recently proposed conceptual interlocking connections (MOD-IT). Additionally, a comparative cradle-to-cradle Life Cycle Assessment (LCA) evaluates the environmental impact and circularity potential of timber modular buildings using this connection system. The study underscores the pivotal role of strategic connection design in achieving a closed-loop system in timber construction. This advancement fosters sustainability by improving efficiency, adaptability, reusability, and autonomy in the construction process.