For the first time in history in 2008 more than half of the worlds population lives in towns and cities and this trend is expected only to continue and with the paradigm shift in urbanization the need to understand that the urban form directly affects habitat, ecosystems, endangered species, and water quality through land consumption, habitat fragmentation and replacement of natural cover with impervious surfaces becomes critical. Actions taken on a single parcel of land can have a ripple effect on the end user of the space, the adjacent property owners, the neighbors, the community and ultimately the region. This is a crucial l time to make people aware of the connections of the built and natural environment. Environmental opportunities exist for energy conservation, material resources efficiency and indoor air quality primarily at the scale of buildings. Additional opportunities for land, air and water quality occur at the scale of regional land use and transportation patterns. By focusing on neighborhoods, the most accessible and ubiquitous form of urbanization, the possibility for positive change is created because it is the environment that widely shared and influenced by the decisions and actions of everyday people. There are countless works of literature and studies devoted to the issue of sustainable neighborhood design but their focus lies mainly among greenfields, a blank canvas. However, with projected population growth and finite land, these greenfield-focused sustainable neighborhood design manuals are not adequate solutions. The reality and challenges today lie with retrofitting existing neighborhoods and the abandoned developments within existing infrastructure with little to no houses; a residual of the housing market collapse of 2008 for sustainability. The key question is how to create a system that helps cities plan for livable neighborhoods by devising streets and corridors that benefit the environment, economic and social fabric of the city. This study will focus those efforts by creating a sustainability index to measure key commercial corridors in the City of Asheville, North Carolina.