Metropolitan planning and development of Australia’s cities for much of the past 75 years has been strongly influenced by what could be termed the “North American model” of low-density, car-dependent suburban development on greenfield master-planned housing estates. The negative social, economic and environmental consequences associated with perpetuating this low-density greenfield model were becoming evident by the 1990s and “compact city” policies began to feature, albeit in piecemeal fashion, in the long-term metropolitan planning strategies of the major capital cities in Australia. This compact city transition, from “suburban” to “urban” (i.e., from a low-density urban form dominated by detached housing with its own surrounding private space to one where there is a significant presence of medium-density and apartment accommodation), remains a challenging work in progress, as reflected in a rapid succession of metropolitan planning strategies—and reviews—for cities such as Melbourne and Sydney since the beginning of this century. Urban infill targets of 70% for new housing construction in these cities now represents a major break with the past and a challenge to the major stakeholders involved in urban development in Australia: state and local government, the property development industry and residents of the established, ageing “greyfield” suburbs that are a focus for intensified redevelopment. This paper comprises four parts. The introduction identifies the multiple challenges confronting 21st-century urban development in Australia. The second part frames transitions required for a regenerative retrofitting of the established suburbs of its major cities, with particular focus on the greyfields. The third section extends transition management research into an examination of the transformative capacity of each of the four key stakeholder groups that are central to achieving such a regenerative transition. To date, the greatest resistance to more intensive redevelopment has come from urban residents. The final section of the paper focuses on this stakeholder group, and draws on data from a major household survey that examines the attitudes of resident property owners in the middle suburbs of Sydney and Melbourne to neighborhood change and medium-density housing development.