During 1995–2010, a comparison of the comprehensive effects of four different types of urban roads on landscape diversity in Shanghai was performed. Remote sensing images from 1995, 2000, 2005, and 2010 and the transfer matrix mathematical model were used to conduct the research, which focused on studying the rule of land use change in the study area over the past 15 years. Seven different landscape indices (SHDI, SHEI, ED, NP, TE, AWMSI, and MSI) were also selected to analyze the landscape pattern of Shanghai in three different periods and to explore the regularity of its dynamic changes and influential factors. Buffer analysis and statistical analyses were applied to represent the relationship between the distance from different roads quantitatively (e.g., railway, highway, national highway, and provincial highway) and a series of landscape pattern metrics (e.g., SHDI, PD, ED, and IJI) thus exploring the influence of transportation routes on the surrounding ecological environment. The results showed that (1) each type of landscape in the study area changed considerably during the research periods, a great amount of cultivated land was transformed into construction land, and the water area largely decreased. (2) The transportation routes exerted different impacts on the road landscape during different periods, and the effects were more obvious at the early stage of road construction. (3) The national way and the highway influenced the patch density (PD) index and edge density (ED) index more clearly, while the national way and the railway had greater effects on the landscape diversity indices. This study presents an approach that can be applied to quantitatively describe the impacts of transportation routes on landscape patterns and has the potential to facilitate route network planning.