Infill development has become a popular strategy for revitalizing old urban districts. However, the construction of new high-rise buildings can cause nuisance issues that are of great concern to indigenous residents. Our study seeks to address three key research questions by examining the impacts of 34 high-rise building typologies within a hypothetical urban context: 1) To what spatial extent does the construction of new high-rise buildings significantly affect their surroundings? 2) How do different tall building typologies modify their surrounding buildings’ outdoor and indoor ventilation potentials? 3) What are the quantitative relations between building geometrical variables and wind performance indicators? The findings reveal that the correlation between building shape and wind behaviors is strongest within a radius of 0.7~1.3H of the target building. Moreover, the study observes that building width, building projected width, frontal area, and shape coefficient can substantially affect indoor and outdoor ventilation potentials of the surrounding spaces, but the influence of these parameters significantly varies depending on the incident wind direction. Certain building typologies can increase the outdoor ventilation potential of the neighborhood by 10–20%. Furthermore, the study employs an elastic net model to investigate the multivariate relations between building geometrical variables and wind performance indicators. The results indicate that the elastic net model outperforms ridge and lasso regression models in predicting wind performance indicators. These findings can enhance our understanding of how to design a tall building within an existing urban configuration.