Shenzhen exemplifies the rapid development of urban planning and construction in China. Over the last 40 years, many representative urban spaces and buildings have been built on Shennan Road, the city’s main eastewest thoroughfare, which has witnessed the formation of a multicenter structural layout and the miraculous expansion of the city. Many iconic buildings were designed by Hong Kong or foreign architects. The continuous development along Shennan Road not only symbolizes the fruits of the reform and opening up policies of Shenzhen and even China, but also reflects the modern architectural history in Shenzhen. This study uses historical research methods to review the changes in the urban fabric and the design trends, as seen in representative buildings along Shennan Road in different periods. In addition to the transition path of the city center, the unique role of streets and buildings in the development of the urban structure is analyzed, and other urban functions and symbolic meanings are identified. This work contributes to the history and theory of the modernization of contemporary Chinese architecture.