Transitioning from work to retirement could be either beneficial or harmful for health. We investigated the association between transition to retirement and risk of stroke and myocardial infarction (MI). We followed US Health and Retirement Study participants age 50+ working full-time for pay and free of major cardiovascular disease (n = 5422) in 1998 up to 10 years for transition to full retirement and self- or proxy-report of either stroke or MI (CVD; 665 events). We used discrete-time survival analysis to compare the CVD incidence for the fully retired versus the full-time working population. To distinguish short-term from long-term risks, we compared the association in the first year after retirement to estimates 2+ years after retirement. In the full model adjusting for age, sex, childhood and adult SES, behavior, and co-morbidities, being retired was associated with elevated odds of CVD onset (OR = 1.40, 95% CI: 1.04, 1.90) compared to those remaining in the full-time labor force. The odds ratio for CVD incidence within the first year of retirement was 1.55 (95% CI: 1.03, 2.33). From the second year post-retirement and thereafter, the retired had marginally elevated risk of CVD compared to those still working (OR = 1.35; 95% CI: 0.96, 1.91). Although confidence intervals were wide for some sub-groups, there were no significant interactions by sex or socioeconomic status. Results suggest that CVD risk is increased after retirement.