The proportion of workers with chronic health conditions (CHCs) will increase over the years as pension reform is increasing the age of retirement in many European countries. This will increase the percentage of older adults with CHCs performing highly demanding work. This study sought to examine the association between common CHCs [cardiovascular disease (CVD), diabetes, arthritis, respiratory and sleep disorders] and three domains of work stress in older Dutch workers. This study used data from the first wave of the NIDI Pension Panel Study for working adults aged 60–65 years (n = 6793). Logistic regression models examined the strength of association between CHCs and (1) general work stress, (2) emotional, and (3) physical demands. All five CHC were independently associated with one or more domains of stress. After including all CHCs in the model, CVD, sleep disorders, and arthritis were significantly associated with general stress. Respiratory disorders, sleep disorders, and arthritis were significantly associated with physical demands. Diabetes (1.25, 95% CI 1.01–1.53), sleep disorders (1.99, 95% CI 1.72–2.31), and arthritis (1.18, 95% CI 1.06–1.31) were significantly associated with emotional demands. Our findings demonstrate that work stress is associated with prevalent CHCs, and these conditions are differentially associated with several domains of work stress in adults approaching retirement. More research is needed to understand the causal relationship between CHCs and work stress. Such research may provide insights for effective workplace and public health interventions to ensure that older workers remain physically and mentally healthy, and productive through their working years.