The current study concerns the analysis of interactive artworks that are located in the public/urban space and use or comment on close circuit surveillance systems (CCTV). For approaching the matter, we focused on two characteristics of the public space, accessibility and communication, that derive from the fields of Political Philosophy and Sociology, as well as the effect that different forms of technology and the New Media have on the way people approach the public/urban environment and interact with it and with each other, and on any artistic content that is located there. Thereupon, the study is directed to the phenomenon of the rise of surveillance of public spaces, presenting historical and sociological/ behavioral data that connect surveillance with the accessibility of the space and the communication between the people in the public sphere. We then mention artistic interactive installations-“ancestors”, that used CCTV in order to comment on the phenomenon, and we later move on to our three study cases. These are: Watch out! The eyes of the city by Maurice Benayoun, Detour by the group VE_design and Street With A View by Robin Hewlett and Ben Kinsley. The analysis of the artworks is based on the effect that each of them has on the accessibility of the environment that is placed in and of the communicational matters regarding its users. We attempt to make observations that compare behavioral parameters that are showcased by the people during the use/participation of/to the artworks and their general behavior in spaces that surveillance has its traditional role and is not linked to an artistic content. In the end, we propose that further research could be conducted regarding the effect of the surveillance art on the way that public spaces are approached and monitored and on the alterations that it may cause on the behavioral patterns of the people.