The UK speculative housebuilding industry has grown and prospered primarily through the conversion of greenfield land into mass, standardised housing estates. As such, the UK Government’s commitment to restricting the development of housing primarily to brownfield sites presents a significant challenge to the current skills base of many speculative housebuilders. Whilst the housebuilding industry has demonstrated in recent years a commitment to brownfield development through the steady increase in the numbers of dwellings built on previously developed land, concerns exists over whether the industry has developed the requisite core competencies necessary to secure a long-term commitment to brownfield development. In response to such concerns, this research assesses the attitudes, behaviours and corporate strategies of a select number of speculative housebuilders towards brownfield development in the English and Scottish contexts. Through this, the research presents a timely and important evaluation of the strategic decision making of UK speculative housebuilders and explores the concept of institutional capacity through an investigation into the private sectors response to public policy change.