High street shopping centres are at the core of cities. The continuing design challenge is to adapt a built environment inheritance to meets the present commercial needs of retailers, maximise the potential of the physical environment and address the social amenities that are expected from a city/town centre public realm. It is in this context this paper addresses the question, what is that makes a successful high street shopping centre? The essence of the analysis is to understand the relationship between property values, location, physical characteristics, diversity of retailing and use, and social vitality within two successful city centre retailing environments. Within the central areas with the highest property values there are overlapping positive scores on indicators of spatial syntax locational measures of integration and connectivity, stationary activities, diversity and visual quality assessment. However, locational factors are more complex than a simple centrality perspective. The message from this paper is that urban design does not need to be concerned with the retail offering, but focus on locational relationships, and the social and physical environment of public spaces. The research also demonstrates the blurring between commercial and public space, and supports Carmona’s argument that successful social space also creates economic value.