Urban sprawl and its economic, social, and environmental consequences are central issues for approaching more sustainable forms of life and production. This review provides a broad theoretical exploration of the main features of urban sprawl but also of sustainable urban policies in Western Europe and North America. Urban sprawl can be observed in both continents, as the search for higher standards of economic, social, and environmental sustainability is also an essential feature of urban governance in the last years. Urban sprawl has been slightly weaker in Western Europe, as its are cities generally more compact. Moreover, in Western Europe, urban sprawl has sometimes been confronted with ex-ante preventive policies. However, in North America, urban sprawl from the 1950s has been an essential element of the social ordering and, thus, of the American way of life. In both cases, urban sprawl has generated successive rounds of accumulation of built capital, which is currently managed in sustainable ways essentially through ex-post and palliative measures, that is, trying to “sustain what is unsustainable”. In other words, the idea is to make urban sprawl more sustainable but without altering its main morphological elements.