A transition to more sustainable cities in Australia will require much greater focus on greyfield redevelopment than previously. With the multiple challenges facing city planning at the beginning of the 21st century---accommodating rapid population growth linked to immigration, attempting more intensive urban development, the need for climate change adaptation and mitigation strategies, and understanding what is required for cities to become more resilient in the face of local and global shocks to their economies and communities---a path of least resistance has seen most recent planning and urban development activity centre on greenfields and brownfields arenas. This paper focuses on the prospects for more sustainable patterns of greyfield redevelopment in Australian cities, with particular reference to Melbourne. Both the Melbourne 2030 and the Melbourne @ 5 million strategies have failed to articulate processes capable of increasing the capacity of existing, ageing, occupied suburban areas---the greyfields---to accommodate projected growth. Greyfield redevelopment at precinct scale offers the potential for jointly transitioning urban housing, energy and water systems---and the residential communities they host---to a more sustainable future.