The Urban planning mission is to produce an image of the future town as it will show after all the developments have taken place. But do Urban Plans and regulations effectively control and guide urban private development? What are the public tools or practices that are used to regulate the current and future urban market through effective land zoning in Italy and in Denmark? How are these tools appraised and considered before becoming effective land regulations? How effective are the different analyzed methodologies in terms of controlling commercial property development and urban quality? And finally, how does the planning and zoning regulations influence the urban property market in terms of property values? The paper will investigate these issues in two European countries, Italy and Denmark, with quite different planning practices as well as quite different property markets.