The purpose of this paper is to use shape grammar methodology to generate contextualized urban façades within the focal context of Naser-Khosrow Street in Iran's capital city of Tehran. The history of Naser-Khosrow Street, which is considered a significant historic urban space, begins in the Safavid period (1735-1501). Yet, the urban history and historical significance of this street have been neglected in recent years. Evidence of a sense of turmoil and incompatibility between the modern and traditional architectural façades featured on the street is easily observed. Against this background, this paper offers façade models generated based on the computational methodology developed by Hadighi and Duarte (2019, 2020) to determine and capture the hybrid expression of European modernist and American traditional styles. In this spirit, the systematic methodology of shape grammar is expanded to the focal urban area of Naser-Khosrow Street to generate new façade layouts referencing the characteristic features of some of the iconic buildings located there.