Green Streets, a stormwater management practice that is implemented within the public right of way, can effectively treat stormwater runoff on-site by closely mimicking natural processes. By providing multiple benefits, Green Streets can, purportedly, be a more sustainable alternative compared to conventional storm systems. However, there is no empirical research that evaluates how, or to what extent, the supposed or potential benefits of Green Streets are actually realized in projects built to date. Thus, planners and designers (or the public who are concerned about their watersheds) will find the literature on the subject to be of limited assistance in assessing many aspects of Green Street projects: their cost in terms of time, money, and resources; challenges; and whether the projects actually achieve the benefits touted by their proponents. This study is conducted to address these issues through two analyses. The first analysis looks at Green Street projects that were nominated by experts as the most successful additions to their communities. This portion of the study reveals that, in current practice, for a Green Street project to be successful, not only does it have to treat stormwater runoff but it also has to offer additional benefits, particularly in relation to the social aspects. The second analysis examines Green Street implementation processes in six sample cities, and four successful Green Street projects that appear to offer additional benefits were chosen for more detailed studies. Finally, a model process was developed with emphasis on the following: site analyses on multiple scales, the formation of interdisciplinary teams, and public outreach throughout the implementation process. The case studies elucidate the given challenges and suggest best practices for ensuring more sustainable outcomes in future projects. The study sheds light on the importance of incorporating multiple benefits in the implementation process and presents eight recommendations for successful Green Street implementation regarding the need for individuals who champion the project, interdisciplinary collaboration, opportunities for the public to voice their concerns, need of expanding the design scope, securing funds as delivering benefits, consideration of the maintenance plan, documentation of knowledge, and development of a model process.