Objective: This study differentiated various living arrangements (ie living with two biological parents, living with one biological parent, living with friends, living in a dorm, and other) and examined its relationship with health-related lifestyles as well as the moderating role of gender differences. Methods: This study used data from the Taiwan Youth Project, a large-scale, longitudinal survey of Taiwanese youths. The data of 2313 sophomore college students who provided full information were analyzed. Regressions were used to examine the association between living arrangements and cigarette smoking, alcohol use, drug use, and physical exercise. Results: Compared to students living with two parents, students living with one parent reported a higher frequency of current cigarette smoking and alcohol use, and students living with friends/alone reported a higher frequency of current alcohol use. The associations between living arrangements and health-related lifestyle, including cigarette smoking, alcohol use, and exercise, varied by gender among college students. Conclusions: Both living in a dorm and living with two biological parents increase healthy lifestyles among Taiwanese college students.