The Women's Health Initiative (WHI), a longitudinal study of more than 161,000 postmenopausal women across the United States, provides an opportunity to investigate the link between sleep health and healthy aging. The purpose of this paper was to systematically review all published WHI articles examining sleep as a predictor of health outcomes and health behaviors/quality of life outcomes. A strength of the WHI is that for most participants, sleep measures were completed before a major health diagnosis, with a significant portion of participants also providing sleep measures after diagnosis. Twenty-three WHI articles were identified and examined for this review. The combination of sleep duration and insomnia symptoms was the most commonly investigated sleep measure. The results indicated that both short (≤6 hours) and long (≥9 hours) sleep duration were associated with a higher risk of cardiovascular disease, colorectal cancer, mortality, cognitive decline, and poor diet. Insomnia symptoms, frequent snoring, and risk of sleep-disordered breathing (SDB) were also associated with increased risk for ischemic stroke and cardiovascular disease. However, many significant results were attenuated after multivariable adjustment. Limitations of these WHI examinations include the use of different categories for sleep measures across studies and a lack of examination by race/ethnicity. Owing to the longitudinal study design, large sample size, and long-term follow-up for health outcomes, the WHI serves as a rich resource for examining associations between sleep characteristics, demographics, and health in postmenopausal women.