Urban designs that consider regional climatic conditions are one of the most important approaches for developing sustainable cities. In cities that suffer from heavy snow and cold winds in winter, an urban design approach different than that used for warm cities should be used. This study presents a scientific design process (the sustainable design approach) that incorporates environmental and energy assessments that use snow and wind simulations to establish guidelines for the design of urban blocks in high-rise and high-density districts so that the impact of snow and wind can be minimized in these cities. A city block in downtown Sapporo, Japan, was used as a case study, and we evaluated four conceptual models. The four models were evaluated for how they impacted the snow and wind conditions in the block as well as the snow removal energy. Based on the results, we were able to identify the design guidelines in downtown Sapporo: an urban block design with higher building height ratio without the mid-rise part can reduce the snowdrifts and lower the snow removal energy. The proposed sustainable urban design approach would be effective in improving the quality of public spaces and reducing snow removal energy in winter cities.