Green roofs are gaining interest as nature-based solutions (NBS) to counteract with several environmental and socio-economic problems associated to urban sprawl and climate change. The challenge is to transform the built environment through the inclusion of NBS. Taking advantage of the existing space in the top of the buildings, the integration of green roofs will support the cities’ transition towards circularity and resilience. They provide several ecosystem services and can act as multifunctional and decentralized units. In order to boost these services, green roofs need to be effectively incorporated and replicated in the urban landscape. Different configuration of systems may be considered depending on the challenges that the city foresees. To fully implement green roofs, it is important that (i) barriers are identified and overcome, (ii) standardization is set to grant liability, (iii) policies, incentives, and strategies are properly established, (iv) organizations delivering NBS services are leveraged, and (v) awareness and dissemination promotion, as investment in education, are considered. This paper intends to give an overview of the importance of green roof integration in the urban environment considering the dimensions of the building and the city, having underlined their contribution to circularity and cities’ resilience.