The conversion of agricultural land for urban usage, such as the formation of residential areas or the establishment of educational institutions is a widespread phenomenon in the outlying localities of India’s small towns and large cities. This chapter explores the process of land transformation on the outskirts of two small towns namely Tiruchengode and Sankagiri in the South Indian state of Tamil Nadu. It describes the practices of different actors involved in land development, namely the landowners, investors, land assemblers and land developers, their actions, and their relationship with the state and with one another. The chapter draws on Sack’s (Human territoriality: its theory and practice. Cambridge University Press, Cambridge, p 2, 1986) theory of human territoriality and Hsing’s concept of ‘civic territoriality’ to conceptualise the process of land transformation in small towns. Further, it develops Hsing’s concept to illustrate the nuanced politics of civic territoriality in intra-community relations and looks at various forms of land tenure to illustrate the role of caste in this context. It reinforces the other contributions in the volume that illustrate the diversity of urbanisation trajectories in India.