Historic cities in India are rich in urban heritage in terms of both tangible and intangible resources and they are in constant state of transformation—physically, socially, and culturally. Every city comprises varied communities based on caste, occupation, religion, etc. These communities act as a catalyst for constant urban transformation in the city. This led to generations of multiple urban typologies of neighbourhoods in the organically grown inner cities generated by community requirements, their social hierarchy in the city and their contribution to sociocultural and economic activities of the city. These cultural transformations can be traced physically in special semiotics features of architectural styles and planning patterns of buildings and neighbourhoods in the historic city, which together contribute to its cultural identityCultural identity. This Chapter focuses on identifying organically grown physical patterns of indigenous neighbourhood typologies in the historic city of ShahjahanabadShahjahanabad. Research is filling the knowledge gap regarding transformation in scale and perception of HaveliHaveli (historically a complex of sub housing units with other amenities for an extended family or a big mansion) focussing on their conversion into heritage MahallasMahalla (Neighbourhoods). Different typologies of sub housing unit belong to different families and are still known today as HavelisHaveli. The evolution of traditional neighbourhoods is studied on available historic maps and live mapping of physical and communal transformations and using typo-morphological analysis as a tool to understand the urban transformation. Research resulted in the identification of active self-organising phenomena, autopoiesis turned into ‘stigmergy’Stigmergy which led to the self-organisation of communities by dividing lots into plots to form new sub-housing units known as HavelisHaveli today. This organic exponential growth is not due to the availability of more space, but to self-generated urban built heritage typologies. They respond to constant community pressure for increasing physical infrastructure, which also gives inhabitants social satisfaction, due to communal integration, sense of belonging, and creates the cultural and socio-economic patterns prevailing in the city.