The objective of this research is to analyze the aerodynamic performance of two complex plan-shaped buildings through experimental investigations. The goal is to investigate the related environment caused by wind forces in both isolated and interacting situations using a prototype model at a scale of 1:300. Four interference circumstances of twin buildings (separately for each model) and isolated conditions with 0° to 180° isolated wind directions were the subjects of experimental testing at the Boundary Layer Wind Tunnel. The investigation was conducted on the most accessible terrain in India, Terrain Category II. A comparison analysis of the two models is carried out in order to comprehend the various consequences of various scenarios that can occur in real-life settings, as well as the discrepancies between them. With only a slight variation in mean Cp magnitudes, experimental results of wind pressure coefficients of Model-1 and Model-2 exhibit good agreement under varied wind incidence situations. Model-1 and Model-2 are slightly varying in shape, based on more streamlined exterior shape modification. Based on wind tunnel tests, it has been determined that Model-2 performs better than Model-1 in both isolated and interference settings for all wind incidences and orientations.