Greater Sydney is expected to be home to an additional 1.7 million people by 2036, making it one of the fastest growing regions in the developed world. Trends suggest that 60% of all new dwellings will be built in established middle suburbs characterised by houses reaching the end of their lifecycle. In the context of the market-driven process of urban redevelopment in Australia, economic feasibility assessment of urban redevelopment needs to be considered. We argue that economic feasibility assessment should be an essential part of the urban design process to create a richer set of evidence to inform design and development of a sustainable precinct, and at the same time lead to proposals that can be realised in practice. This paper presents and evaluates a case study illustrating the tension between design envisioning and its economic feasibility in market-driven urban development. Using a precinct in Western Sydney as a case study which proposed a redevelopment design based solely on socio-environmental goals, this paper assesses the economic feasibility of the proposed design using a GIS based economic feasibility tool. The results from the tool indicated that the proposed design options are not financially feasible under the current market conditions of the case study area. These findings reinforce our argument that economic feasibility should be incorporated as an essential part of the design process. The agility, flexibility and high visual quality, coupled with the economic feasibility metrics of these digital tools in providing feasibility outcomes make it suitable for such design processes.