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This article explores the tensions between China’s newly privatized model of urban housing ownership and its socialist foundations. Through a combination of interviews and local research, the authors investigate the evolution of property ownership in Shanghai’s architecturally-distinctive stock of historic housing, encompassing various architectural periods and styles (including leading examples of Art Deco), which have gone through periods of private ownership (pre-1949), gradual socialization (1949-1965), militant squatting and occupation (1966-1976), and now privatization (1977 to current). Originally single-family residences, many were gerrymandered into multi-family units, in which the original owner/resident was relegated a small portion of space, and the remainder divided (by governmental assignment or squatting) among other residents. Now that land values in Shanghai have risen, there is increased interest in selling or renovating these houses (which are located in key sites in central Shanghai) or redeveloping the sites. However, the rights to develop or transfer these properties remain complicated due to ongoing issues regarding the rights of the original owners versus later residents/squatters. In the face of this impasse, a dynamic known as “the tragedy of the commons” has developed in which none of the parties has assumed responsibility for maintaining and improving the buildings or their common areas. As these formerly majestic pre-1949 residences increasingly fall into disrepair, they become vulnerable to demolition and replacement by shiny, new complexes. Unfortunately, if events follow this path, Shanghai will lose a key part of its architectural character and flavor.