Greenways are networks of some connected linear elements that are designed and programmed for a variety of recreational, cultural, aesthetic, and some other purposes. Therefore, the purpose of this study is to check out the land cover changes around the Azadi Street in past and to predict its future changes. This is done in order for checking the connections of the green spaces around the street, connecting Azadi Street and its surroundings, providing solution for future planning and management, and applying greenway principles. For this purpose, using remote sensing techniques, we extracted land cover maps from satellite pictures of years 1986, 2000, and 2016. We used CA-Markov integrated model to predict future changes—in year 2032. The results demonstrate a decrease of 474 ha of the green spots’ area while there is an increase of 658 ha of the built lands during 1986–2016. If the security and management plans on the street area are not going to be changed, this area will transform to a machine-centered space and the limited level of the existing walking-oriented area will disappear soon. The results of this research are effective in reviewing the management approaches of the region so that by providing effective solutions, they can lead the policy makers and planners to follow some of the principles of greenways.