Since the mid-1990s, urban development authorities in India prioritized private sector participation and public–private partnerships for land and housing development. This chapter explores the practices of land and housing development, promoted by two urban development authorities, namely the Haryana Urban Development Authority and the Delhi Development Authority. Drawing on Harvey’sn ‘entrepreneurial urbanism’ and Goldman’s, speculative urbanism thesis, this chapter explores the manner in which PPP projects have materialized in practices. It exposes the practices of real estate developers and the new planning instruments adopted by urban development authorities to facilitate the transfer of valuable land to private developers. It suggests that the turn towards real estate development and the PPP differs from the earlier entrepreneurial models adopted by the urban development authorities. The PPP model, based on an incentive of tapping real estate gains serve more as an instrument of facilitating high premium land to developers at a cheap cost. The argument is elaborated through two case studies of PPP for land and housing development for upper income groups and squatters. The trajectory of these projects shows that large developers projects are either incomplete or unoccupied. Both projects have resulted in conflicts between developers, land owners and residents of squatter settlement. In these conflicts, the development authorities have acted more as brokers for developers.