Istiklal Caddesi, once the Grand Rue de Pera during the Ottoman Empire, was renamed to stand for independence and liberty. Since at least the 18th century, the space of the avenue has been the site for viewing diverse peoples and experiences, and displaying mixtures of built forms and styles. It acts as an iconic indicator of the changing direction of Turkish modernity. This paper considers the long history of this street from the Ottoman era to the present and puts forth a framework for observing how street space takes part in creating urban identities bound and defined by architecture and the people who traverse and inhabit these places. Real estate development in the late 18th, 19th, and 20th centuries densely filled in open spaces or replaced the old with new buildings. Adding top the character of the area, sometimes a parcel, or several of them combined, was design with an ingenious interior passage, courtyard or arcaded space that served to join both the avenue and surrounding side streets. Stylistically, hybridizations of form, decoration and use blended to expose a cosmopolitan European sensitivity that was integrated within the Turkish and Levantine multi-story structures. This kind of integration is suggestive of an acceptance of outside secular activity in a Muslim Empire. The introduction of the Wealth Tax in 1942 eroded previous periods of transformation and acceptance by forcing ethnic and sectarian others out of their city spaces. This essentially halted outside influence, thereby censoring spatial use and urban development in Istanbul. By the 1960s, Istiklal Caddesi had fallen into disrepair and ill-repute. The rebirth came in the late 1980s under Ozal’s economic reforms, which boosted the Beyoglu district and invited outside retailers and fast food establishments into a mix of local businesses. In the 1990s, Turkish bank foundations, speculative commercial developers, and individual tenants began to develop and integrate cultural centers into the mix. Continuing in the 2000s art and commerce became even more connected, bringing about additional questions concerning issues of preservation, re-adaptation and re-making new local and global culture. At the same time,recent real estate development policy is threatening this newer urban character with large-scale commercial buildings such as Demiroren, which has inspiredstrong debate about the public values along with state intentions. A disproportionate breakdown of urban and architectural quality appears to be at stake in the name of progress.