The aim of this paper is to illustrate the impact of urban wind environments when assessing the availability of natural ventilation. A numerical study of urban airflow for a complex of five building blocks located at the University of Reading, UK is presented. The computational fluid dynamics software package ANSYS was used to simulate six typical cases of urban wind environments and to assess the potential for natural ventilation. The study highlights the impact of three typical architectural forms (street canyons, semi-enclosures and courtyards) on the local wind environment. Simulation results were also compared with experimental data collected from six locations on the building complex. The study demonstrates that ventilation strategies formed using regional weather data may have a propensity to over-estimate the potential for natural ventilation and cooling, due to the impact of urban form which creates a unique microclimate. Characteristics of urban wind flow patterns are presented as a guideline and can be used to assess the design and performance of natural or hybrid ventilation and the opportunity for passive cooling.