The benefits of Water Sensitive Urban Design (WSUD) are increasingly being recognised in terms of reduced flood risk, reduced cost of drainage, improved water quality, lower energy use and other, less tangible aspects, such as aesthetics and amenity. Multiple tools and evaluation techniques exist to estimate the costs and benefits of installations on a total level. These evaluations vary in accuracy and precision and many benefits are difficult to monetise. There are also distributional aspects of costs and benefits that will need to be considered in the ongoing dialogue to encourage appropriate installation of WSUD that have, thus far, rarely been explored in research. In particular, the perspective of the commercial real estate owner, investor or occupier has been neglected in favour of governmental and societal views. This can be understood within the wider context of urban design such as retention or infiltration installations in public spaces; in Central Business Districts (CBDs), however, the retrofitting of green roof technology is seen as one of the main contributors to WSUD and is largely in the hands of private companies. A conceptual model of the distribution of benefits from installing a green roof on an existing commercial building is presented that can inform the understanding of incentives and behaviours in the corporate real estate market. The results show that benefits accrue directly and indirectly to both owners and occupiers of commercial buildings with green roofs. However, many of the direct benefits are enjoyed by a much wider stakeholder group and these benefits will only be partly recognised as due to the investment in green roofs. Owners and occupiers of commercial buildings may also want to evaluate the indirect benefit accruing via their image of corporate social responsibility and, in addition the possibility of value uplift due to neighbourhood improvement.