This study investigates the association between chronic health conditions (CHD) and depression with a focus on the mediating effect of financial strain. We tested if age makes any difference in the effect of CHD and financial strain on depression. The data comes from the 2006 Korea Longitudinal Study of Aging (KLoSA) collected by the Institute of Korean Labor Research. The sample consisted of information from 8,961 individuals ages 45-79. Separate analyses were done for middle-age (45-64) and older-adult groups (65-79). There were significant financial portfolio differences among CHD patients and non-CHD, for both age groups, that may constitute the impact of a health event on financial wellbeing; in addition, the associations of CHD on depressive symptoms were different by age groups. The mediating effect of financial wellbeing on the association between CHD and depressive symptoms was verified; in addition, the role of financial wellbeing on the association was especially strong for the older-adult group. The effect of CHD on depression was contingent on the amount of net assets and annual personal income. Implications are discussed based on the findings.