One feature of contemporary urban life has been the widespread transformation, by middle-class resettlement, of older inner-city neighbourhoods formerly occupied by working-class and underclass communities. Often termed ‘gentrification’, this process has been a focus of intense debate in urban study and in the social sciences.This case study explores processes of change in Toronto's inner neighbourhoods in recent decades, integrating an understanding of political economy with an appreciation of the culture of everyday urban life. The author locates Toronto's gentrification in a context of both global and local patterns of contemporary city-building, focusing on the workings of the property industry and of the local state, the rise and decline of modernist planning, and the transition to postindustrial urbanism.Drawing on a series of in-depth interviews among a segment of Toronto's inner-city, middle-class population, Caulfield argues that the seeds of gentrification have included patterns of critical social practice and that the 'gentrified' landscape is highly paradoxical, embodying both the emerging dominance of a deindustrialized urban economy and an immanent critique of contemporary city-building.