Urban Transformation is a continuous phenomenon that prevails between diverse scales and many contexts. The leftover spaces as a result of growing urban developments respond to macro, meso and micro scales. They remain a continuous challenge and need a contextual approach to create a sustainable urban development. This paper deals with challenges that urban left over spaces pose towards the on-going urban developments for smart cities and future urban growth. A micro level, low tech design intervention in an urban left over space in New Delhi i.e. Dilli Haat forms the key basis to illustrate the idea. It is showcased as a typical design typology emerging in urban Indian contexts for open and vacant pockets of urban lands, usually lying unattended and unutilized. Using DepthmapX, this paper analyses the spatial configuration of the case and informs about the diverse characteristics of urban public place. By using in situ observation and space syntax methodologies, this paper assesses the design qualities for this successful design typology. This paper is centred on a conviction that context plays a vital role in sustainable urban developments and spatial analysis methods of space syntax as an approach is used in order to analyse and understand the process of transforming an unused urban left-over space in the heart of Delhi into a vibrant Dilli Haat (market place) for its neighbourhood and further into an attraction that foreign tourists visit. Furthermore this paper hypothesises that interdependence and interlinkages of urban voids play a vital role in creating sustainable urban environments. It highlights the role of spatial configuration, visual permeability and accessibility in creating meaningful public spaces.