Ecological and social challenges have tested the ability of conventional land development as a route to a sustainable future. Early sustainability paradigms have been part of the response towards better development practices, but many critics have argued that more needs to be done – to move beyond essentially degenerative sustainability paradigms towards more explicitly regenerative sustainability paradigms. This practicum examines the Canada Lands Company (CLC) development of its CFB Calgary properties (Garrison Woods and Currie Barracks) to explore the progress around sustainability paradigms and to prospect the case for Regenerative Design and Development (RD+D) as a new operative worldview governing CLC’s planning and land development practices. A literature review and a series of focused interviews with key informants were the main research methods, within the context of the case study set, to pursue a series of research questions, culminating with: How – and in what ways, with what rationale – could RD+D be considered an appropriate new worldview for CLC’s next generation of leading-edge-seeking projects? What are its prospects? It was generally concluded that RD+D is a viable, emerging sustainability approach for CLC. More specifically, on the basis of this research, CFB Calgary was assessed as having been developed with what may now be defined as a green approach – implicitly sustainable, in aspiration at least; the next progression on this would involve a more explicit sustainable approach, then restorative, all laying the ground for a potentially regenerative approach. If RD+D had been the operative worldview during inception and execution of CFB Calgary, there would almost certainly have been a very different process and outcome. However, it would probably require a dedicated champion of RD+D, within CLC, for this post-conventional sustainability approach to be seriously considered. The Company’s track record – as an innovative land developer – encourages the view that RD+D could well be a good fit – as a potential next-generation planning and development approach.