We investigated associations of work–family conflict and work and family conditions with objectively measured cardiometabolic risk and sleep. Multilevel analyses assessed cross-sectional associations between employee and job characteristics and health in analyses of 1,524 employees in 30 extended-care facilities in a single company. We examined work and family conditions in relation to: (a) validated, cardiometabolic risk score based on measured blood pressure, cholesterol, glycosylated hemoglobin, body mass index, and self-reported tobacco consumption and (b) wrist actigraphy–based sleep duration. In fully adjusted multilevel models, work-to-family conflict but not family-to-work conflict was positively associated with cardiometabolic risk. Having a lower level occupation (nursing assistant vs. nurse) was associated with increased cardiometabolic risk, whereas being married and having younger children at home was protective. A significant Age × Work-to-Family Conflict interaction revealed that higher work-to-family conflict was more strongly associated with increased cardiometabolic risk in younger employees. High family-to-work conflict was significantly associated with shorter sleep duration. Working long hours and having children at home were both independently associated with shorter sleep duration. High work-to-family conflict was associated with longer sleep duration. These results indicate that different dimensions of work–family conflict may pose threats to cardiometabolic health and sleep duration for employees. This study contributes to the research on work–family conflict, suggesting that work-to-family and family-to-work conflict are associated with specific health outcomes. Translating theory and findings to preventive interventions entails recognition of the dimensionality of work and family dynamics and the need to target specific work and family conditions.