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Real estate assets are an essential resource at the threshold of retirement, when households enter this new stage of the life cycle and can consider new residential projects or dissaving by selling a property. But these real estate resources are held very unevenly across social categories and generations. The aim of this article is to account for the disparities in the real estate wealth of households around the age of 60, by looking at the ownership of the main residence as well as that of other dwellings (secondary residence or investment property). Using the 1973 to 2013 housing surveys, we provide an overview of these inequalities within and between the generations born between 1910 and 1954, by setting their life courses in the socio-economic context in which they took place, which may or may not have fostered home purchasing. We show that homeownership has spread over the last fifty years has not been uniform across generations and social categories, with inequalities crystallizing at the threshold of retirement. Economic contexts and housing policies have thus largely favored the constitution of real estate assets for the 1935-1950 generations, but at the same time social inequalities have been reinforced and amplified due to the increasing complexity of family trajectories.