Although retirement involves a radical change in daily activities, income, social roles and relationships, and the transition from paid work into retirement can, therefore, be expected to affect sleep, little is known about the effects of old-age retirement on changes in sleep disturbances, and how the impact of retirement may vary by gender, age and prior working conditions. This study modelled reported sleep disturbances up to nine years before to nine years following retirement in a sample of 2,110 participants from the Swedish Longitudinal Occupational Survey of Health (SLOSH). Sleep disturbances over the retirement transition were modelled using repeated-measures regression analysis with Generalized Estimating Equations (GEE) in relation to gender, age at retirement, working patterns (night work, full-time/part-time work), control over work hours, and psychological and physical working conditions. The analyses controlled for civil status, education level, income obtained from registers and self-rated health. Retiring from paid work was associated with decreased sleep disturbances. Greater reductions in sleep disturbances were reported by women, as well as by participants who retired before age 65 years, who were working full-time, who lacked control over their work hours and who had high psychological demands. These results, suggesting that old-age retirement from paid work is associated with reductions in disturbed sleep, pose a challenge for governments seeking to increase retirement ages.