Gradual changes in social sphere, politics and economics (in context of Czech Republic accentuated in last twenty-five years of rapid growth following neo-liberal shift in planning policies and urban management) have serious impact on transformation of forces that are shaping our cities nowadays. Notable increase in range of project sizes (often including large portions of public space), varying typology and forms of development, shift in periodicity of changes in urban structure results not only in ambiguity in current notion of “public” and “private” both in spatial sense and division of responsibility, but as well in disconnection between planning tools and real processes in built environment, thus increasing instability and “fuzziness” in roles and responsibilities within the system. In this context, the master planning system can hardly be derived only from institutional responsibility. The paper therefore explores alternative point of view on decision making process in urban planning and architecture, based purely on built environment and its parameters. The layers of urban environment (public spaces, built mass, infrastructural systems, programmatic pattern etc.) are examined and systemized using case studies of different urban setting and theoretical models. The research sets up a comprehensive framework of singular planning decisions that consequently form the urban structure by studying syntactic units of built environment and their role in different scale levels. In today’s situation demanding flexibility in decision-making process, the results can serve as a ground for optimization of urban planning processes, standards and legislation.