Urban intensification seems to be a growing trend, especially in the context of severe land scarcity. Brownfields offer great potential in meeting the increasing demand for housing in major cities worldwide. Redevelopment projects appear to provide immediate solutions to housing shortages that are being experienced due to population pressures in large metropolitan areas. The paper explores the range of factors that property developers need to consider in their decision-making process when assessing the viability of brownfield redevelopments. This research, which employed a comparative case study approach, and examined two brownfield redevelopments in Auckland, focused on the economic, social, and environmental criteria that were utilised in the decision-making process. Document analysis of the two case studies, site observations, and semi-structured interviews with the property developers were the main data collection methods. The results suggested that the economic aspects of a brownfield redevelopment are the most important criteria that developers consider during the feasibility assessment of proposed projects. Projects that offer the potential for quick investment returns for all stakeholders are the preferred choice for developers. Brownfield redevelopments offer significant potential for invigorating local areas through urban intensification which boosts local businesses and encourages community revitalisation. The environmental concerns appear to be the lowest priority and little consideration is given to reducing the environmental impacts or incorporating green building practices in the new developments. A major shift from a purely economic focus toward a comprehensive environmental approach to new developments is needed to ensure the sustainable development of cities.