The process of urbanization in Romania was a very tumultuous and slightly different one compared to other Central and Eastern European countries, being marked by the constant willingness to increase the degree of urbanization. The communist period was the most significant from this point of view, by considering both the number of newly declared towns and urban population growth. The urbanization of communist era corroborated with the excessive and forced industrialization has generated imbalances in the urban system and created distortions in the urban hierarchy. However, the legislative inconsistency and the lack of urban regulations during the post – communist period have lead to the increasing number of new (quasi) urban units (many of which without urban amenities) to the chaotic sub-urbanization of cities and urban decline. In many cases, the ability of local authorities to manage the urban development in the early years of transition has been hampered by inadequate legislation that regulates the urban growth in a completely different socio-economic system. Thus, the lacks of specific urban policies and urban regeneration plans have determined indirectly a hypertrophic evolution and an uncontrolled suburban expansion. Bucharest, the capital of the country has been most affected by these processes determining multilayered space transformation within the city and open space conversion to commercial and residential use, both affecting the urban environment and quality of life of urban-rural communities. The paper focuses on the patterns, the driving forces and the consequences of two opposing processes: socialist forced urbanization vs. post-socialist chaotic urbanization unfolding across the national urban landscape.