Objectives In older adults, traditional metrics derived from polysomnography (PSG) are not well correlated with subjective sleep quality. Little is known about whether the association between PSG and subjective sleep quality changes with age, or whether quantitative assessment of EEG (qEEG) is associated with sleep quality. We therefore examined the relationship between subjective sleep quality and objective sleep characteristics (standard polysomnography and qEEG) across middle to older adulthood. Methods Using a cross-sectional analyses of 3,173 community-dwelling men and women ages 39–90 participating in the Sleep Heart Health Study, we examined the relationship between a morning rating of the prior night’s sleep quality (Sleep Depth and Restfulness) and polysomnographic and qEEG descriptors of that single night of sleep, along with clinical and demographic measures. Multivariable models were constructed using two machine learning methods, lasso penalized regressions and random forests. Results Little variance was explained across models. Greater objective sleep efficiency, reduced wake after sleep onset and fewer sleep to wake stage transitions were each associated with higher sleep quality; qEEG variables contributed little explanatory power. The oldest adults reported the highest sleep quality even as objective sleep deteriorated, such that they would rate their sleep better given the same level of sleep efficiency. Despite this, there were no major differences in the predictors of subjective sleep across the age span. Conclusion Standard metrics derived from polysomnography, including qEEG, contribute little to explaining subjective sleep quality in middle-aged to older adults. The objective correlates of subjective sleep quality do not appear to systematically change with age, despite a change in the relationship between subjective sleep quality and objective sleep efficiency.