Coastal cities in the Mediterranean region have cool sea breezes that can reduce the effects of global warming, urban heat islands (UHI), and air pollution. However, in many coastal cities, impermeable urban seafront buildings prevent cool sea breezes from penetrating the city while at the same time posing a risk of pedestrian wind discomfort. This study aims to design wind-adaptive urban seafront buildings that improve urban ventilation and pedestrian wind comfort in Izmir, a high-density Mediterranean city, using the parametric design and computational fluid dynamics (CFD) method. Alternative seafront buildings consisting of two-rows and shifted configurations were designed using the two proposed urban geometric indicators. The authors found that the denser and more compact seafront building configuration can prevent the risk of wind discomfort and achieves the highest ventilation efficiency (82%). The findings apply to similar coastal urban environments and help urban policymakers and designers.