The green retrofit of old residential areas is an important approach to promote urban renewal and to realize the sustainable development of existing buildings. However, the various risks in retrofit projects hinder the progress. In this study, a list of risk factors of retrofit projects in Old Residential Areas (ORAs) is built from whole life cycle of a project, the opinions of participants on the possibility of risk factors and the degree of impact on the project were collected through the questionnaire survey, a risk assessment model based on C-OWA and grey cluster analysis is developed to evaluate the risk, and risk management and control are proposed based on different risk levels. A case study is carried out by taking a retrofit project in Chongqing A-zone as an example to assess the comprehensive risk in this project, and corresponding recommendations for risk control of the retrofit project are provided. The research findings provide references for risk management of retrofit project in ORAs.