Indian streets exude vitality, energy, and variety owing to a rich work culture, authenticity, and reliability. Core city’s traditional streets like Lohaoli, Chunaoli, and Kiranaoli based on metal-work, lime-work, and grocery shopping respectively, possess a distinct image due to the predominant occupation amidst the residential spaces. This study focuses on Chitaroli, an urban street in Nagpur, renowned for idol and sculpture-making. The street culture is studied considering (a) socio-economic (context, work culture, people, and economy); (b) spatial qualities (land use, and access); and (c) place-making aspects (condition of buildings, residential unit, and sociability) through the spatial analysis and the household survey. The research identifies issues such as congestion, traffic problems, poor housing and sanitation conditions, degenerating architecture, declining realms, and economic challenges. The recommendations are presented to regenerate and conserve Chitaroli, with the study framework offering insights for restoring other streets and reinstating occupants and their occupations.