Transportation has been regarded as a significant facilitator and barrier to accessing jobs and a range of basic urban services and opportunities. Availability of car, for example, is known to increase access to healthcare services, thereby improving public health outcomes in cities. Scholars, however, are concerned about physical inactivity and associated diseases due to increasing motorized personal transportation use and declining use of active travel modes such as, bicycling and walking. Policymakers are getting worried about deteriorating physical activity and fitness, rising obesity, and increasing incidence of illnesses like diabetes that stem from physical inactivity and sedentary behavior not only in developed but also in developing countries like India. Although many studies have tried to study the association between motorized vehicle ownership and lifestyle diseases in India, they were either limited to a small section of population or focused on specific diseases. Thus, the present study aims to study the association between: (a) household motorized vehicle ownership and lifestyle diseases (obesity and diabetes), and (b) household motorized vehicle ownership and accessibility to preventive healthcare in a nationally representative sample of men in India. Using data from India’s National Family Health Survey, we find that owning motorized vehicle was significantly associated with obesity as well as preventive care visits to a healthcare facility among men, but not with diabetes. It indicates a public health conundrum. Motorized vehicle ownership has a negative role in promoting lifestyle diseases like obesity but can still facilitate accessibility to preventive healthcare, thereby promoting health. Transportation policies must consider this public health puzzle.