“Cul-de-sac” is in common a residential dead-end street. However, it is an important urban element used for articulating vernacular housing in the Arab cities to form a wide range of cluster. It has also a main role of providing a safe and healthy environment for residents, which is suitable for social domestic activities. This paper aims to highlight a potential idea to recover the concept of vernacular Cul-de-sac but in a contemporary way. Thus, we will try to shade light on a modern type of residential streets, which is the upper street that functions as a main stem for articulating houses around it. This type of streets was named in the modern movement as a “Street in the sky”. Thus the paper investigates the connection between streets in the sky and the vernacular Cul-de-sac, by discussing a famous case of the modern housing: Habitat 67, which is cluster housing around layers of streets in the city of Montreal. The paper concludes that, the upper streets of cluster housing are an adequate approach for recovering the vernacular Cul-de-sac in terms of social and visual aspects, since it could combine characteristics of both vernacular Cul-de-sac and the street in the sky.