Glenn Murcutt is nowadays recognized as one of the most influential environmental architects of the century. His design philosophy, environmental awareness and in-depth understanding of the Australian context and vernacular architecture, have led him to become one of the leaders of critical regionalism worldwide. His buildings aim not only to provide shelter, but to lower their environmental impacts through simple, yet innovative design solutions. Murcutt’s buildings are well documented and published, nevertheless, they have not received much academic attention and limited evidence based research and publications are available to assist holistic understanding of his work. Through a critical review of two of his most celebrated projects (i.e. the Ball-Eastaway and Marika-Alderton house), the authors aimed to fill this research gap. Although the selected houses share a similar building typology, their location, orientation, materiality and environmental requirements greatly differ. While the Ball-Eastaway was conceived as a relaxing habitat, embedded in a secluded bush land in NSW and the main design concept was to exploit the local landscape and views, the Marika-Alderton house was designed as a climate responsive shelter for an aboriginal family on the seaside of Eastern Arnhem, NT. By conducting theoretical qualitative and quantitative analysis, the close connection between the spatial quality, environmental design strategies and performance of the two houses were thoroughly studied. Through this study, the effect of these elements on Murcutt’s unique way of materialising environmentally conscious buildings was revealed. The research outcomes indicate that even though both buildings experienced occasional visual and thermal discomfort, they performed well for most of the time as intended free-running buildings, proving that their constant connection with the exterior greatly affects their internal comfort conditions. Through his environmental design principles, Murcutt’s buildings are sensibly designed to be adaptable, spatially delightful and to have a low carbon footprint, while having a continuous dialogue with nature. The significance of Murcutt’s work lies precisely in this delicate liaison between his romanticism and practicality.