Many North American suburban shopping malls have become under-performing retail islands drifting in oceans of asphalt parking lots. This thesis examined three potential future scenarios for the aging retail shopping mall landscape; 1. Maintaining status quo 2. Upgrading the property for a mixed-use neighbourhood centre 3. Implementing strategies for attainable sustainability targets These scenarios were examined using a proposed retrofit of Edmonton, Canada’s Westmount Centre as a case study, to determine if this retrofitting approach could be a pilot for other districts. The principles of 2030 District (2030 District, 2012) guided this thesis, a concept which proposed that by 2030 all newly constructed districts be energy neutral and that existing districts be retrofitted to use less than 50% of the energy that they presently consume. The Spider charts developed by Haas & Troglio (Haas & Troglio, 2011) were used to create strategies that included incorporating existing proven, economically viable technologies to the proposed retrofit. The three resulting scenarios were then evaluated using Leadership in Energy and Environmental Design - Neighbourhood Design, version 4 (LEED-ND v4), to make a case for raising the threshold for sustainability and mitigation measures when planning new and retrofit projects in North America (USGBC, 2014). The goal of the thesis was to find a solution that holistically meets the goals of LEED-ND, where partnerships between numerous stakeholders provide a business model for urban sustainability, which includes planning, implementation and verification (2030 District, 2012). By examining proven sustainability measures and applying them to the normative scenario, makes the case that strategic implementation during a situation of opportunity, through timely stakeholder interaction, will result in a district that is both sustainable (environmentally, socially and economically) and provides a good return on investment. This thesis is a starting point for the iterative process, a compelling argument and business case for further investigation and action for Westmount Centre and by extension, to other retail districts.