The demand to reduce the use of raw materials, construction waste, and the negative environmental impacts of the construction sector is constantly increasing. New circular design strategies, such as Design for Disassembly, are intended to meet these challenges. Furthermore, circular strategies facilitate the easy and quick replacement of building components during end-of-life phases, as well as the efficient and waste-free deconstruction of entire buildings for subsequent reuse. However, building structures developed according to these strategies can have a higher environmental burden in the production or use phase of their life cycle. To confirm the actual environmental benefits of circular constructions, the paper utilizes the Life Cycle Assessment (LCA) method as a vital tool for the environmental evaluation of circular structures. As a case study, fully demountable and conventional masonry building façade systems with insulation are analyzed through a cradle-to-cradle approach over 2 life cycles. Several End-of-Life scenarios, as well as reuse and the benefits it provides, were considered during the assessment. Examining eight environmental indicators, the comparative analysis of linear and circular facade design approaches in the chosen case studies provides insights into efficient and environmentally friendly solutions.