Abstract: It is necessary to determine how to appropriately expand the scale of leisure agriculture entities under constraints of existing resources and effectively promote sustainable development of urban leisure agriculture for realization of large-scale operational willingness of urban leisure agriculture entities limited to resources and policy restrictions of metropolises. Based on questionnaire data of 87 leisure agriculture entities in Shanghai, this study constructed a Logistic-ISM (interpretation structure model) model and took the willingness of leisure agriculture entities as measurement targets to study significant factors that affected the willingness, and logical hierarchical relationships between factors. Results showed that moderate expansion depended on the influence of the three levels of factors: 1) Among deep-seated factors, the leisure agriculture entities supported by government construction land were more willing to expand the scale of farmland. 2) Among middle-level indirect factors, the characteristics of agricultural resources, scientific park planning, innovative management capabilities, and business industrial structure positively affected the willingness of leisure agriculture entities to expand the scale of farmland, while the ecological nature of agricultural production was strong, the expansion of operators’ willingness to farmland size was weak. 3) Among the direct factors at the surface level, culturally functional leisure agriculture entities were willing to expand the scale of farmland, while leisure functional management entities tended to reduce the scale of farmland. To promote moderate scale operation of urban leisure agriculture, the government should introduce state-owned enterprises to play a demonstration effect to revitalize stock of rural land resources, and release value of resources. At the same time, leisure agriculture should provide strategic space for urban core functions, fully consider the heterogeneity of leisure agriculture entities, dig deep into rural cultural heritage, and promote transformation from undertaking the function of guaranteeing the supply of agricultural products for multiple functions to highlighting the economic, ecological, and esthetic values of agriculture and rural areas.