The purpose of this study was to examine the influence of chronic disease, physical function, and lifestyle on health transitions among the middle-aged and older persons in Taiwan. A longitudinal design was applied to investigate whether chronic disease, physical function, and lifestyle were associated significantly with health transition in this population. Data on participants were obtained from the Survey of Health and Living Status of the Middle Aged and Elderly in Taiwan, a study initially conducted in 1999 that encompassed observations on 2,130 individuals 53 years and older. Data were collected again in 2003 to capture the health transition. A binary probit model was used to determine relationships between health transition and sociodemographic factors, chronic disease, physical functional ability, and lifestyle conditions by gender. Principal empirical results confirmed that, after controlling for potentially confounding variables, those participants who were relatively younger and had higher education levels were more likely to maintain good health during the study period (1999-2003) for both men and women. In addition, when other factors were excluded, this article identified stroke as the ailment most strongly associated with continuing good health. Similarly, activities of daily living and instrumental activities of daily living demonstrated significant and negative effects on continuing good health regardless of gender. However, lifestyle rendered interesting and plausible findings. Smoking showed a significant influence on health transition for women but an insignificant influence on such for men. Regular exercise showed significance for both men and women. Findings suggest that chronic disease, physical functional ability, and lifestyle variables have strong and significant influences on health transition for the middle-aged and older persons. Research results should be useful in developing strategies that target disease care services and lifestyles for the target group.