A communication quality evaluation system, a device, a method, and a program for evaluating communication quality at an arbitrary location, in the form which can actually felt by a user, are provided. According to an instruction from an evaluator, a control device displays a map or layout diagram of a specified area on a map/layout diagram display device and specifies an evaluation point within a display range of the map or the layout diagram. According to the network quality estimated by a network quality estimation unit, a network quality simulation unit for estimating the network quality when communications are performed at the evaluation point deteriorates the evaluation data and transmits the data to an evaluation device. The evaluation data deteriorated is a sample of data actually transmitted and received in the communication system. The evaluation device uses a communication device actually used by a user in the communication system.