Society is evolving faster and faster and there are many changes in our everyday living environment, especially concerning buildings. Buildings have significant effects on the ecosystem, economy, health, and productivity of the people occupying them; moreover, their environmental impact is not limited to the energy consumption for heating, cooling, moving, and lighting, but it affects many other factors, including above all the relationship with the territory. Considering these premises, this research focused on suggesting sustainable guidelines in Italy by trying to identify what has changed in the methods of residential construction, especially in order to meet new environmental and people’s requests. The research purpose is to focus on the concept of property value, trying to identify some guidelines that increase the value of housing according to the mutated market requests observed by a representative sample of real estate agents. As a result, a new property concept aimed at high quality and sustainability standards, co-housing, and dynamic scenarios pushed up by the increasing demand from new generations, such as single, high-educated young workers and university students, lead us to explore the solution of short-term rents in the Italian territory. This solution appears in a real estate market heavily affected by the economic crisis, and is a good alternative for owners or landlords, which is able to guarantee a positive return on investment and to assure a major capability to keep value in the long term.