In today’s highly technical and rapidly changing world, the topic of people-friendly living has become increasingly acute. Therefore, great attention is paid to create new spaces (and transform unpleasant ones). In this race to create new spaces, however, vernacular sites that are already people friendly have been forgotten or they are taken for granted. This article explores a neighborhood, which has evolved into a valuable living environment after hundreds of years of development characterized by weak planning and design. Current efforts to regenerate the area may actually ruin the valuable vernacular environment. The authors have worked with this historic area for over 10 years and are familiar with the people and environments in depth. This longitudinal research allows one to observe and compare many different aspects of urban development (urban analysis, people’s values, adopted spatial plans, etc.) to provide insights to the question of what characterizes the lively city.