The design of sustainable constructions also resilient to climate change has become a challenging issue given the increasing greenhouse emissions rate imputable to the built environment in urban areas. In this context, dynamic simulation models represent a suitable tool to support the design from very preliminary phases, since they allow an accurate prediction of the constructions requirements, their environmental performance, and indoor comfort conditions for their occupants. Therefore, starting from specific inputs, that is, weather conditions, construction technologies, materials, energy systems, operation settings, occupancy, and so forth, it is possible to estimate the realistic building energy performance. Moreover, the calibration procedures allow making the model even more representative of the field conditions of a construction. Given the massive progress carried out by the scientific community during the last decades, this paper presents a comprehensive review of the different building dynamic simulation approaches and available tools. While previous review studies focused on single separated aspects of dynamic simulations approaches, that is, calibration methods, software, simulation of single building energy systems, the aim of the present review is to propose a more holistic approach by investigating the recent scientific progress in simulating realistic dense urban environments. In this view, the review focus bridges the gap between the simulation at single-building level and simulation at the increasingly important neighborhood scale by showing the multiple benefits deriving from using dynamic simulation tools at district level, for a more reliable investigation of building performance in their urban context, where more than 50% of the global population worldwide currently lives.