One could say that heritage issues divide Romanian society into three. Most of the civil society wouldn’t care about heritage and the thin layer of the rest of it is divided among two opposing forces in permanent clash. One side wishes nothing to be touched and the other wants to change everything. Between these two opposing groups there is no communication bridge as one part speaks only about memories and the other one only about money. No argument seems to be taken into account in order to understand that there is no need to believe that someone should lose money if one should keep the heritage in place and that it is not necessarily true that making some money from real estate is impossible unless all heritage is gone. But what kind of information should be considered in the process of deciding the balance? In order to illustrate the path a certain real estate investment should follow in a protected area, the case of an historic monument in Revolution Square in Bucharest is presented. Historic data about the evolution of the urban configuration of this public space show that a coherent square of the Capital was obtained through expropriation and regulation of the built area, generating one of the most iconic urban space in Bucharest in the interbellum period. Once it was demolished in 1940, a void was created and for almost 75 years this place became one of the most destructurated one in the city. For this reason, two urban planning competitions in half a century were organized and another architectural one led to the reconstruction of a house devastated in December 1989, resulting in one of the most controversial buildings in the country today. As the space remained destructured for so many years, people now have mixed opinions regarding the possibility of rebuilding there. Although present regulations allow and in a way impose rebuilding, civil society tend to oppose to any attempt of doing so. Press articles are showing indignation about the height of a proposed building on the private plot of land of the “Cina” restaurant but omit the fact that for over a century, right on the other side of the axis of Athenée’s garden there is a hotel of 5 levels over the ground floor that are actually equivalent to the opposed block of flats in Calea Victoriei that have 8 floors over the high ground floor with mezzanine. So, is it that urban planning in historic sites becomes a question of better communication or a question of better knowledge about the local values and liabilities? It might be observed that also in Chișinău, in at least three situations, the issue of building or rehabilitating in an historic context was not the main problem. All three investments could have been done by maintaining in the same time the historic characteristics of those specific heritage buildings. It appears that the only thing missing was the correct analysis of the cultural aspects so that they could have been identified and integrated in the new projects. Preparing for incoming funding and determining the limits of interventions on historic buildings and specific areas of the historic centre is the only way for avoiding further decay of public space and for a more harmonious real estate development, with no frictions among the “conservationists” at all cost and “progressive fanatics” for nothing.