The literature on social and wealth inequality has long acknowledged the importance of intergenerational wealth transmission (IWT) to inequality in homeownership tenure. However, it has paid insufficient attention to the institutional structures that moderate these inequalities. Therefore, in this study, we ask how institutional factors via differential housing finance systems and governmental housing policies, moderate the association between IWT and homeownership tenure. This is done by using the framework of housing regime configurations and mortgage market financialization. To do so, we pooled data for 20 European countries from the European Central Bank’s Household Finance and Consumption Survey (HFCS) for 2010–2017, for household heads aged 25–40. Our main findings show consistent contradiction to the welfare state–homeownership “trade-off” hypothesis: that is, when the rental market is more heavily regulated, it is actually young adults who benefited from IWT or who received higher value of IWT have a higher probability of mortgaged homeownership. Paradoxically, when housing finance institutions are more active and generous, the wealthiest young adults hold an advantage in mortgaged homeownership. Therefore, liberal mortgage markets actually serve to enable wealthier young adults to reproduce and preserve their parental wealth status. Further, when housing prices are less affordable (median mortgage-to-income ratio), those who have received a higher amount of IWT hold an advantage in mortgaged homeownership. We discuss the implications of our findings, which cut across the socioeconomic, spatial, and demographical arenas.