Europe’s population is ageing. Statutory retirement ages are commonly raised to account for continuous increases in life expectancy. In order to estimate the potential to increase statutory and consequently effective retirement ages further, in this study, we investigate the relationship between partial working life expectancy (WLE) and three health expectancies that represent health aspects important for work ability and employability between ages 50 and 59 as well as 60 and 69 for women and men in Europe. We also explore the association between these four indicators and the highest level of educational attainment. We apply Sullivan’s method to estimate WLE and three selected measures that capture general, physical, and cognitive health status of older adults for 26 European countries since 2004. Over time, WLEs increased significantly in the younger age group for women and in the older age group for both sexes. The expected number of years in good physical health have continuously been higher than any of the other three indicators, while the expected number of years in good cognitive health have shown a noticeable increase over time. The investigation of the relationship between education and each life expectancy confirms the well-established positive correlation between education and economic activity as well as good health. Our results indicate potential to extend working lives beyond current levels. However, significant differences in the expected number of years in good health between persons with different levels of education require policies that account for this heterogeneity.