Uncertainty of spillover effects – including property devaluation - from proposed land-use change elicits opposition to local development. This hinders cities’ ability to implement land-use policy aimed at housing affordability and environmental sustainability. The uncertainty arises from the limitation of current methods to quantify both the physical exposure and financial sensitivity to changes in urban environmental characteristics and amenities. Hence, this paper introduces an integrated approach to quantify the direct and indirect effects of a proposed urban development, using parametric modeling, building performance simulation and automated design appraisal (ADA). ADA, a novel aspect of this study, predicts the market price of a generated building design concept within a local urban context. To demonstrate its practical utility, this paper examines property value at risk due to nearby development associated with changes to visual landscape quality. The results shed light on the importance and spatial variability of the price-amenity gradient, identifying properties that are financially at risk to the visual impacts of local development. Beyond building-specific risk modeling for the development planning stage, this work serves as a blueprint for architectural design optimization procedures, in which economic performance is evaluated based on learned preferences derived from financial market data.