The entire urban planning history of Kalaallit Nunaat/Greenland falls within living memory, and the history of urban design needs to be documented. We have studied the evolution of urban space design through selected residential projects from different periods of the country’s planning history. We mapped the design context, use and perception of these projects through fieldwork in both winter and summer. The spatial analysis is discussed in relation to urban policies and local inhabitants’ experiences with, and attitudes towards, neighbourhoods. Finally, planning controversies were mapped through a media study. Constructing an urbanised society was instrumental to the colonial-era centralisation and assimilation policies. Having moved from social engineering towards capital-driven urban development in a brief period, the compact planning and urban design history exposes tensions between outside experts and local desires in a governance system rapidly moving towards Indigenous autonomy. An account of the emergence of a postcolonial urban design culture can be instructive for sustainable future urban development in Greenland and enable urban comparison with other urban territories within or outside the Arctic.