India is the country that shelters the highest number of poor. Most of the underprivileged class is residing in rural parts. As a consequence, urban poor are being neglected for decades. How better is the urban poor compared to their rural counterparts is an issue of concern. Whether the poor of the small and medium size towns or cities are finding their livelihood relatively better than what they are getting in large cities or metropolis is a subject of serious research from policy point of view. This paper tries to throw light on the demographic aspects, health condition and utilization of health care facilities of the poor residing in three places namely, large cities, medium towns and countryside. The data used for the analysis is the National Family Health Survey II (1998 -99), which incorporates the household and individual information of women aged 14-49. Results indicate that though economically, urban poor is better off compared to their rural counterparts, wider gap exists between the rich and the poor of large cities with regard to the indices of fertility and mortality. Child and under-five mortality are the highest among the poor of large cities. At state level, Maharashtra no way presents a better representation of the poor residing in Mumbai compared to the other urban centers or even villages in terms of women’s anemia level, body mass or contraceptive use. Even, the level of anemia among the poor women is significantly lower in non-metros of Maharashtra. In West Bengal too, poor of urban areas other than Kolkata and those residing in villages are considerably less anemic. Tamilnadu proves an insignificant difference among the poor by their place of stay in terms of body mass as well as anemia. However, contraceptive use is significantly more among the poor inhabiting in Chennai. It is increasingly becoming evident that the overburdened big cities cannot address the social problems beyond a certain critical mass. Hence, it is necessary to promote the mid size towns and cities as a model to effect a significant qualitative improvement in the life of the underprivileged section