Cities have been the focus of recent sustainability and climate change mitigation efforts primarily because of unprecedented urban growth and ever-increasing resources consumption. A worrying trend has been the ever-decreasing life of buildings in cities because of premature building obsolescence. Premature building obsolescence has been cited as the major driver of demolition waste which accounts for more than 40% of total waste generated annually. This waste stream poses a bigger challenge as the pressure on natural resources increases with urban growth. A traditional way of looking at the urban sustainability has been from the perspective of the environmental sciences and waste management methods. Analyzing urban areas with design science perspectives could provide novel insights to improve existing resource consumption patterns and transform sustainability growth in cities. This study focuses on the problem of demolition waste arising from the premature building obsolescence in cities. It applies a design research methodology framework for identifying existing problems associated with demolition waste and generating strategies to transform cities into more sustainable urban systems. In the problem clarification phase, a detailed literature review was supported with stakeholder’s interviews to identify the state-of-art for building demolition process and demolition waste. Research was further extended to descriptive study-I phase to carry out a demolition case study and generate support tools to enable transformation in the existing scenario for achieving a desired state. Singapore, a dense city state of SouthEast Asia has been taken as a case study in this research. Results show that applying design research methods could help open-up a new dimension to solve urban sustainability challenge for built environment. It highlights that material reuse could lead to significant improvement in the built environment sustainability but the challenge associated with realization of material reuse practice needs to be addressed. Descriptive study-I concludes with the strategies on creating a reuse market through entrepreneurial innovation and an alternative material supply chain of secondary materials for regional housing demand. These results highlight the role of design research methods for tackling complex systems level problems in cities.