Property developers and investors have been at the forefront of urban regeneration in the UK since the 1980s. This has produced an emphasis on prime office space, luxury apartments, shopping centres and leisure attractions, which has been widely criticised on social equity grounds. But there has been only limited interrogation of the failure of property-led regeneration to deliver on the development it promises or on whether it represents good value for public money. Nottingham Eastside is one such example of market failure, where over a 25 year period, property developers and investors have come and gone, none of four masterplans have been implemented, decontamination and infrastructure provision has never been completed, and most of the land is still vacant. By reconstructing the story of Nottingham Eastside and evaluating its experience against Jessop’s strategic-relational approach, this paper asks whether it is now time to create an alternative place-based model of urban development, drawing on best practice from continental Europe.