Property management (PM) service has been becoming the essential service for office buildings in the age of building stocks. In this study, we investigate how PM affects the rent of office buildings. 51 office buildings which are of small and middle scale in Shinbashi Area are selected for analysis. Criteria based on “kansei” judgment (the subjective judgment) of evaluators are proposed as the basis of evaluating the degree of maintenance and upgrade. Their values are derived by the field work and are integrated into the ordinary building specification and site environment data. Decision tree and rent prediction analyses are carried out. Through these analyses, we will show findings such that standard deviations of kansei judgment which are roughly discretized are important factors for rent prediction, and so on.