Many young people in Europe face employment insecurity, a condition which will likely persist following the global economic downturn that started with the financial crisis of 2007–08. Previous research has shown that employment insecurity impedes the entry into homeownership. It is, however, less clear how this delayed entry into homeownership is filtered by contextual arrangements at the country level. Using longitudinal data from the EU Statistics on Income and Living Conditions (2007–11), we confirm prior findings on the negative effect of employment insecurity across European countries. We also find contextual variations. In more marketised housing provision systems in Northern and Western Europe, where mortgages are readily available to those in secure employment, the negative effect of employment insecurity (relative to having secure employment) on the transition into homeownership is accentuated. In more familialistic systems with strongly regulated labour markets in Southern Europe, the difference between young people in different employment situations is smaller, yet still significant. We find similar-sized differences between those in insecure and secure employment in the Baltic States, but not in the other Eastern and Central European countries, where housing shortages impede the entry into homeownership for young people across different employment positions.