Objectives: This study examines educational differences in living alone and in self-rated health trends among middle-aged and older adults. Methods: We used logistic regression to analyze data from the 1972–2018 National Health Interview Survey ( n = 795,239 aged 40–64; n = 357,974 aged 65–84). Results: Between 1972–1974 and 2015–2018, living alone became more prevalent, particularly among men and at lower levels of education. Self-rated health trends varied by living arrangement and education. We found self-rated health declines among middle-aged adults having no college degree and living alone, but trends in self-rated health were mostly stable or even improved among middle-aged adults living with others. Among older adults, self-rated health improved over time, but for the least-educated older Americans living alone, the probability of reporting fair or poor health increased between 1972–1974 and 2015–2018. Discussion: The findings suggest growing disparities by social class, in living arrangements and in self-rated health.