In modern cities, the roof of multi-rise buildings is one of the primary visual contents when viewing from high-rise buildings. Due to the window view content being a significant factor affecting restoration, different roof types might affect restoration potential. However, limited literature has focused on the restoration effect of different roof types. Therefore, this study examined the association between the perception of roof type by the Perceived Sensory Dimensions (PSDs) and the restoration potential by the Short-version Revised Restoration Scale (SRRS). In the stepwise regression model, four variables of PSDs (i.e., Serene, Nature, Social, and Rich in species) have a significant linear relationship to predict the restoration. A series of analyses of variance (ANOVA) and post hoc tests evaluated differences in restorative effects based on the site, the roof type, and the floor level. The experimental analysis showed that the viewing floor level has no significant difference in the assessment of restoration when we focus on surrounding building roofs. This result might be due to the characteristics of window content, such as environmental openness, enclosure, and visual complexity. Meanwhile, viewing the garden roof from higher floor levels (i.e., 9 F and 27 F) has a better restorative effect than viewing the flat roof, the slope roof, and the grass roof. The empirical findings suggested that buildings’ surrounding environments significantly correlate with the restoration of window view. Furthermore, when high-rise buildings are surrounded by multi-rise residential buildings, choosing the garden roof as a renovation method benefits restoration over the flat roof, the slope roof, and the grass roof. This study encourages researchers and practitioners to design psychologically sustainable urban environments by linking different roof types with restoration.