To be able to overcome the urban challenges of tomorrow (climate change, overheating, vacancies, CO2-dilemma, mobility-issues) a thorough knowledge of the Stadtparterre and its characteristics is needed. In order to maintain and enhance the potential of our Bestandsstädte it is necessary to be able to read and understand their (internal) organisation. By covering the public street-space, the adjacent ground floor zone and the courtyards, the UPM (Urban Parterre Modelling) method enables a coherent analysis of streetscapes. This qualitative approach aims to capture the microstructure of the urban parterre in order to visualise the systemic interdependencies of its parts. In doing so, street-spaces and their buildings are reconstructed in their historical and current states. The approach is rather labour-intensive, as hundreds of archive plans have to be checked on site for accuracy and use-structure and transferred to a coherent three-dimensional model. By simplifying this process without losing the key elements, UPMsmart makes the qualitative approach scalable and opens it up to quantitative research. It operates on a typological layer by producing a collection of highly detailed pre-modelled building typologies (covering structural design, and historic/current uses) using publicly available data like building footprints and street facades. This information is connected with the three-dimensional building object, resulting in simplified digital twins (CAD-model). This opens up the option of expanding the original scope of the UPM from selected street segments to larger scales, and of reconstructing and analysing entire urban tissues, thus contributing to the idea of CIM (City Information Modelling). The paper introduces UPMsmart as a new method to analyse streetscapes as well as urban patterns in a larger scale. As part of the research project EMC2, the method is being applied in Vienna's urban periphery, where a wide variety of settlement, street and building-typologies present a particular potential for the development of street-spaces.