The subject of this article is historical urban development, localization-specific and cultural urban heritage of the Georgian capital city of Tbilisi. All the urban development periods, from the very beginning until today, are described in a chronological order. Also, the author discusses general legal principles of urban space development applicable in this country. In all the cases, the author seeks to clarify the legislation problems and to discuss some examples of urban management of the twenty-hundred-years-old urban space. The text is based on the: (1) urban rehabilitation and revitalization documentation of Tbilisi, prepared in 2000 within an international project financed by the European Council and The Georgian Cultural Heritage Foundation, published in Strasburg in Georgian, French and English languages (Tumaniszwili 2001), (2) empirical documentation prepared in 2003–2006 within the international Project AIA and (3) historical documentation gathered in Georgian and foreign libraries in 1998–2008.