The heritage value of the historic urban countryside, as a remnant in the transition between the urban boundary and the natural environment, is a consequence of the spatial and temporal evolution of the city. However, through repeated social transformations, the conflicts between urban construction and cultural landscape heritage preservation have increased, resulting in the gradual disappearance of their cultural landscape heritage. This study takes the Sheshan Urban Countryside Historic District in Shanghai and interprets the layers of Sheshan's cultural landscape heritage into five periods, Emergence, Development and Exploration, Diversity and Prosperity, Turbulence and Change, and Stability and Precipitation. It analyzes the evolution of the layers of the cultural landscape heritage by applying Historic Urban Landscape Historic Land use Assessment (HUL) and interpreting the layers of the cultural heritage of Sheshan using Historical Landscape Assessment (HLA) to identify the characteristics and values of Sheshan's layers of heritage. The study indicates that the cultural landscape heritage of Jiufeng Sheshan exhibits four types of stratigraphic relationships: accretion, juxtaposition, overlay, and decline. This findings suggest a continuous evolutionary feature of superposition of multiple stratigraphic patterns. Moreover, the heritage value of the cultural landscape layers of Jiufeng Sheshan has shown a higher growth rate in the modern period. The integrity and survival status of modern religious and scientific buildings are more complete compared to the literati gardens and Buddhist relics. Based on the knowledge and value assessment of its cultural landscape heritage, it is necessary to intervene in the concept of living conservation and renewal of landscape heritage. This involves devising a conservation and renewal strategy for cultural landscape heritage that conforms to the law of historical stratification and connect the scattered historical and cultural relics. This study provides a reference for the conservation and inheritance of cultural landscape heritage in urban countryside historical areas and the organic renewal of urban and rural heritage.