Our cities are facing different kinds of challenges-in parallel to the urban transformation and densification, climate targets and objectives of decision-makers are on the daily agenda of planning. Therefore, the planning of new neighbourhoods and buildings in high-density areas is complex in many ways. It requires intelligent processes that automate specific aspects of planning and thus enable impact-oriented planning in the early phases. The impacts on environment, economy and society have to be considered for a sustainable planning result in order to make responsible decisions. The objective of this paper is to explore pathways towards a framework for the environmental performance assessment and the optimisation of high-rise buildings with a particular focus on processing large amounts of data in order to derive actionable insights. A development area in the urban centre of Vienna serves as case study to exemplify the potential of automated model generation and applying ML algorithm to accelerate simulation time and extend the design space of possible solutions. As a result, the generated designs are screened on the basis of their performance using a Design Space Exploration approach. The potential for optimisation is evaluated in terms of their environmental impact on the immediate environment.