The enhancement of Modern Heritage buildings is nowadays a challenging issue as they are often degraded or abandoned and their historical value is not well acknowledged by potential buyers and their owners. Moreover, they are usually energy inefficient and obsolete, but investments for energy retrofit interventions are not always convenient, especially in socio-economic contexts characterized by weak real-estate market dynamics. This paper aims to study the influence of intrinsic and extrinsic characteristics on housing prices and, in particular, to understand whether elements of building cultural connotations or some housing green features are monetized by the real estate market. The UNESCO site “Ivrea, industrial city of the 20th century”, located in the weak real-estate context of the Eporediese territorial area, was selected as an emblematic case study and two data samples of property listings were built to perform spatial regression analyses. The results showed that the green features of housing, such as the heating type and the EPC level, have a greater influence on property prices than those characteristics related to the cultural connotations of a building, such as the Olivettian context. Therefore, the current incentive-based policies for energy efficiency can represent great opportunities that can be exploited both to preserve and to improve the condition of this valuable Modern Heritage.