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The urban landscape is by nature the result of many cultural and natural factors and processes. Cityscape associated with land attributes and human activities expresses a city's social and economic functions. Treescape in the form of species composition, tree dimension and tree performance echoes ecological and environmental functions. The cityscape can be denoted by urban factors, such as tree growing-space condition, tree management regime, human activities and planting history. The hypothesis that the cityscape plays a key role in molding the treescape is tested. Nanjing, an east China city notable for its high tree coverage, is chosen as the study area. A quantitative method has been developed to assess the relationship between cityscape and treescape. Based on statistical analyses on the surveyed results of 6527 trees and related cityscape attributes, this paper explores the pertinent patterns and underlying factors of treescape variations. Species composition has the strongest association with cityscape. Roadside and factories have lower species diversity. Residential and industrial land uses show smaller tree dimension. Trees in residential, commercial, heavy industrial land-uses perform below par. A three-way classification has been developed to examine the effects of urban factors on treescape at different cityscape scales. At the small scale, a well-vegetated groundcover will ensure better tree performance and a lower management burden. The medium-scale cityscape (land-use and habitat) is preferred in the study of treescape attributes and their spatial variations, and is suitable for urban tree planning and management.