Although previous research shows that family dynamics and parental socio-economic status influence the timing of young adults? first entry into homeownership, much less is known about how the role of family factors may vary across countries with different housing systems. In this paper, we use panel survey data from Britain and Germany to compare how family life course careers and parental socio-economic background influence young adults? initial entry into homeownership in these two divergent national contexts. The results show that in Britain, first-time homeownership transitions are tightly synchronised with partnership formation. By contrast, in Germany first moves into homeownership typically occur later around or after the arrival of children. Parental owner-occupation accelerates entry into homeownership in both contexts, while the effects of other parental characteristics are relatively muted. Furthermore, the results highlight how individual socio-economic factors are critical determinants of entering owner-occupation. This is particularly true in Britain where there is a strong socio-economic gradient in first-time homeownership transitions.