BACKGROUND: Despite the actual demographic trends and the global burden of cardiovascular diseases, there is little knowledge concerning the effects of retirement on this health outcome. OBJECTIVE: We aimed to quantify the associations between retirement, and retirement age, with cardiovascular disease (heart disease and stroke) in the Portuguese population. METHODS: We used data from the first Portuguese wave of the Survey of Health Ageing and Retirement in Europe. Logistic regression was applied to quantify the associations. The major risk factors for cardiovascular diseases and several features of retirement were considered as possible confounders or effect modifiers. Analysis was restricted to retirees in retirement process (retired for 5 years or less) and not retired because of illness. RESULTS: An opposite direction of the association between retirement and heart disease was observed according to hypertension status, although not significant. Early retirement increased the odds of having a stroke, merely in individuals without heart disease (OR = 8.87; 95% CI 1.63–48.26). On the contrary, in individuals with heart disease, decreased the odds of having a stroke (OR = 0.08; 95% CI 0.01–0.68). CONCLUSIONS: Our findings suggest that retirement and retirement age may be beneficial or harmful, respectively, in the presence or absence of major risk factors for heart disease and stroke. We suggest that work-related stress affecting differently workers with and without these risk factors may eventually explain these findings.