At the end of the first decades of the twentieth century, the Southwestern part of Novi Sad, then the marshy ground, through urbanization and introduction of infrastructure, became an elite residential area which it still is today. Villas, grouped in blocks, built on rectangular land lots, bounded by the garden, were usually designed combining the customer’s (investor) wishes and the ability of professionals – architects. By analyzing the various sociological aspects, with the critical focus on town planning conditions and construction rules, as well as through a comparative analysis of individual villas, this paper will attempt to explain whether the benevolent attitude towards the specific contexts in which certain architectural heritage is created is but a consequence of a time distance.