The history of urban development is a story of the constant patterning and transformation of the city landscape. More rapid and more institutionalized with the advent of capitalism, this transformation process can be seen as a constant structuring and restructuring of urban space, with nothing remaining untouched for very long. The opening up of the Indian economy since 1991 has brought about much change in large cities, and the process of restructuring is more evident in metropolitan cities than anywhere else. This chapter explores the impacts of urban restructuring upon old neighbourhoods of Kolkata, dwelling upon the changes in built-up spaces, creation of new and evolving social spaces that create a sense of alienation amongst older residents, while the neighbourhood itself is transformed with multiple positive changes that are much appreciated by the younger generation and especially the upwardly-mobile middle class. It is a complex task to weave together often conflicting views as respondents talk about increasing gaps between the rich and the poor, the gating of residences legitimising the age-old neighbours as ‘outsiders’, and the excitement brought about by ‘choices’ of branded consumer goods showcased in the brightly lit, resplendent malls.