Concerns about the quality of living environment have been in the focus of spatial planning since the very beginning of the discipline. The idea that the physical form of the environment could affect social and economic wellbeing or even determine the quality of life has been quite central to planning thought. Although the understandings what makes a good living environment and how could it be achieved have varied greatly over time, the recent sustainability paradigm in spatial planning has been seen as a ‘common good’ to improve process/procedural approaches, alongside substantive/design approaches.Our paper is taking a closer look at the planning procedures and documents in four valuable residential neighbourhoods in Tartu and Tallinn, Estonia. The historic residential districts near the city centre constitute remarkable cases for contemporary spatial planning with great potential in achieving the three E-s - environment, economy, and equity - of sustainability and demonstrating a strong “spirit of place”. We are presenting a critical analysis of strategic comprehensive plans and theme plans of the neighbourhoods, looking at the theoretical approaches lying behind the planning solutions. The description of Estonian planning system and factors influencing it (like Soviet legacy) are given for background information.The general purpose of the comprehensive plans in historical neighbourhoods is both to preserve the historic physical character of the district and to ensure the residents good living conditions. The new buildings and extensions of the existing ones should not overuse the site and take advantage of the sparse density of neighbouring plots.In Estonian planning framework, comprehensive plans can be changed by detailed plans, which provide the obligatory grounds for issuing the building projects and permits. Although the planning act sees this as an exceptional procedure with possible alterations carefully considered, it was a common practice in the beginning of the century. In our analysis overview of the detailed plans and new buildings constructed over the years in research areas is given. The magnitude of the alterations is assessed as well as the conformity with the comprehensive plans. Thus the detailed plans and new buildings indicate the scale, pace and character of the actual developments in built environment.The conclusions deal with trends of development in historical residential neighbourhoods. Future potential of the research areas supported by current comprehensive plans is envisaged and suggestions for the planning practice are given.