Key life-course transitions often instigate, or even require, at least one residential move. Leaving the parental home, coupling or separating are clear examples. Life-course transitions therefore also have clear and inherent spatial dimensions, but the question how life course plays out at small spatial scales is rarely studied in a structured way. Instead, we often have to make-do with crude generalizations such as seemingly stable urban–suburban dichotomies. In this chapter, we challenge this perspective by providing a new framework to analyze contemporary changes in the regional dynamics of life course. Housing plays a key role in this: housing market conditions structure the degree to which individuals are able to make transitions. Contemporary housing transformations, taking place in most Western countries, have an unequal impact on different generations. In many successful cities housing affordability and accessibility are decreasing. This leaves a mark on life-course trajectories, as the trade-offs involved in making certain transitions become sharper – in terms of housing and space. Housing transformations therefore contribute to a changing geography of life course within urban regions. We illustrate our arguments through a case study of life-course dynamics in the Amsterdam metropolitan region in the wake of the 2008 Global Financial Crisis.