The thesis titled “Three Urban Squares: Bridging the Urban with the Rural through Building Regulations and Common Spaces” aims to explore potential ways in which urban expansion can occur within the vacant space at the city’s edges. The character of this void is semi-rural, reminiscent of the countryside, typically unorganized, lacking comprehensive planning, with cultivated areas, industries, and even residences developing within it. The only requirement is that these activities adhere to the definitions set by specialized protection terms (such as zoning regulations, etc.), and buildings comply with the construction rules defined by the urban planning code. Urban expansion should not only respond to urban planning zone regulations but also to another planning tool, the “Building Regulations,” applied uniformly throughout the Greek territory, resulting in visible uniformity and homogeneity of the urban space. The purpose of the study is to push the New Building Regulation to a critical state, as this point will indicate whether we can deviate from the beaten path of the last 12 years of its implementation. Through specific articles of the regulation concerning construction, coverage, planted open spaces, maximum heights and reference points, lateral distances, open and closed balconies, semi-outdoor spaces, and passage arcades, an attempt will be made to find new models of building arrangement, settlement, and exploitation of open land in a 4.3 ha area in the suburbs of the city of Volos. The area selected for development comes after studying the 2016 General Urban Plan of Volos and the areas proposed for residential development. Although the consensus is the redevelopment of building stock in other areas, for the sake of the study, a “tabula rasa” is necessary to examine all possible manifestations of laws on a field unaffected by the restrictions brought by the fragmentation of large areas into small land parcels. With this in mind, the final proposal includes a residential complex with communal spaces on the ground floors of the buildings at street level and a unified open space that serves the entire community as an urban garden.