The paper argues how the sustainable development of entrepreneurship in urban areas is based on four cornerstones: corruption, size of urban areas, industrial structure and cultural biases. Corruption is a significant social and economic issue that has crippling effect for entrepreneurship. Further on, the superiority of larger cities in generating advanced economies has been recognized since the time of the ancient Greek and medieval Italian city-states, however it is not clear if the same is applicable today as well. Third cornerstone of entrepreneurial development in main urban areas is the industrial structure of these areas. Lastly, the values that drive entrepreneurial action and form entrepreneurial environments are embedded in wider national culture. The aim of the paper is to investigate and describe pivotal influences on entrepreneurial activity as an impetus of sustainable economic development in globalized environment of transition economy urban areas. The four factors that influence the level of sustainable development of entrepreneurship in urban areas: level of perceived corruption, size of urban areas, industrial structure and cultural biases are described as well as the correlation between level of entrepreneurial activity and each of these crucial elements of urban revitalization. By examining antecedents and consequences of economic and social circumstances that define environment for fostering entrepreneurial activity in main urban areas in Croatia the paper provides comprehensive tool for strategy development that can be used by policy makers and entrepreneurs alike.