The literature suggests a positive link between homeownership and the transition to parenthood. However, in recent decades, couples' preference for becoming homeowners before having their first child has been undermined by rising housing unaffordability and housing uncertainty. An archetypal example is Britain, where homeownership rates among young adults have fallen substantially as a result of low wages, unemployment, reductions in the availability of mortgage credit, and rising house prices. This situation has produced a housing crisis. Using longitudinal data from the British Household Panel Survey (1991–2008) and the United Kingdom Household Longitudinal Study (2009–2016), we apply multilevel, discrete-time event-history techniques to a sample of women aged 18–42. We investigate whether and how the link between homeownership and entering parenthood has changed in Britain in recent decades. Our findings reveal that in comparison with the 1990s, the likelihood of becoming a parent has declined among homeowners, whereas childbearing rates among private renters have remained stable. Thus, owner-occupiers and private renters have become more similar in terms of their likelihood of entering parenthood. Overall, our findings question the classical micro-level assumption of a positive link between homeownership and transition to parenthood, at least among Britain's “Generation Rent.” These findings are subsequently interpreted in terms of increased housing uncertainty.