This paper proposes a novel method to identify unexpected structures in 2D floor plans using the concept of Bayesian Surprise. Taking into account that a person’s expectation is an important aspect of the perception of space, we exploit the theory of Bayesian Surprise to robustly model expectation and thus surprise in the context of building structures. We use Isovist Analysis, which is a popular space syntax technique, to turn qualitative object attributes into quantitative environmental information. Since isovists are location-specific patterns of visibility, a sequence of isovists describes the spatial perception during a movement along multiple points in space. We then use Bayesian Surprise in a feature space consisting of these isovist readings. To demonstrate the suitability of our approach, we take snapshots of an agent’s local environment to provide a short list of images that characterize a traversed trajectory through a 2D indoor environment. Those fingerprints represent surprising regions of a tour, characterize the traversed map and enable indoor LBS to focus more on important regions. Given this idea, we propose to use surprise as a new dimension of context in indoor location-based services (LBS). Agents of LBS, such as mobile robots or non-player characters in computer games, may use the context surprise to focus more on important regions of a map for a better use or understanding of the floor plan.