We explored personal factors that can predict health-related lifestyles of community-dwelling older adults. A convenience sample of 253 older adults was recruited to complete the Health Enhancement Lifestyle Profile (HELP), a comprehensive measure of health-promoting behaviors. Data were analyzed through univariate correlational/comparative statistics followed by stepwise multiple regression analysis to determine significant predictor variables for different aspects of health-related lifestyle. Personal health conditions, including the number of chronic diseases or impairments and self-rated health, were two strong predictors for the HELP (R2 = .571, p < .0001). Demographic characteristics, including age, gender, race, education, and employment status, also demonstrated varied degrees of capability for predicting the different HELP scales (e.g., Exercise, Diet, Leisure). When developing individualized plans for older adults in community settings, occupational therapists should consider the clients’ strengths and vulnerabilities potentially derived from personal health factors and demographic attributes to yield more effective lifestyle interventions.