This paper seeks to ignite a conversation about the potential roles of different legal paradigms in working towards healthier, happier, more environmentally regenerative approaches to our cities. Processes of urbanism bring together and drive the vast majority of our socially and environmentally cataclysmic systems and dynamics – including unsustainable transportation, agriculture, land use, energy generation, water management, and consumption/production practices. Thankfully, there are a host of emerging alternative approaches to, and technologies for the creation of human built environments that can help address, rather than accelerate environmental and social problems. In high consumption countries such as Australia, however, a host of legal and regulatory rules have largely locked in inequitable and unsustainable urbanism. Accordingly, this paper seeks to engage with the broader question of whether existing legal doctrines – and particularly doctrines of property, condominium/strata, and corporation are appropriate tools for and/or barriers to more regenerative approaches to creating regenerative cities.