Shanghai witnessed an early development of green roofs (GRs) of great potential but has been focusing on the increase in construction rather than the management of maintenance, which prevented the effective achievement of ecological benefits in a GR’s lifecycle. This paper used Google Earth satellite images to interpret the constructed GRs in the central urban area of Shanghai from 2008 to 2020, conducted statistics on the numbers of new-built GRs and existing ones year by year and district by district, calculated the growth rate of construction per year and estimated the duration of GRs. Combined with the previous policies, official data, and practice surveys, problems existing in the construction and maintenance of GRs were analyzed, and suggestions were put forward for future development. The results showed the non-garden-oriented construction of yearly new-built GRs in Shanghai, the significant variation of year-to-year growth in new-built amount, the continuous accumulation of yearly existing GRs, the better situation of GRs in garden type, the differences in the construction and duration of GRs among the districts (i.e., Jing’an, Huangpu, and Pudong districts constructed more GRs while the GRs in Hongkou district have presented better duration), as well as the shorter duration of non-garden GRs than the garden GRs. The problems in the construction of GRs in Shanghai are mainly reflected as follows: (1) The type of structure of GRs needs to be optimized; (2) The policies presenting significant supports need to be further implemented and improved; (3) The experiences of GRs construction in each district need to be explored and summarized; (4) The duration of non-garden GRs need to be improved. The suggested strategies are: (1) Policies should guide the direction of GRs development; (2) Technic innovations should develop local GRs products of lower maintenance; (3) Management should improve the green roof construction and maintenance market.