This paper presents a control-oriented dynamical model of a towing rope system with variable-length. In this system, a winch driven by a motor's torque uses the towing rope to pull a cart. In general, it is a difficult and complicated process to obtain an accurate mathematical model for this system. In particular, if the rope length is varied by operating the winch, the varying rope dynamics needs to be considered, and the key physical parameters need to be re-identified... However, real time parameter identification requires long computation time for the control scheme, and hence undesirable control performance. Therefore, in this article, the rope is modeled as a straight massless segment, with the mass of rope being considered partly with that of the cart, and partly as halfway to the winch. In addition, the changing spring constant and damping constant of the towing rope are accounted for as part of the dynamics of the winch. Finally, a reduced-order observer-based servomechanism controller is designed for the system, and the performance is evaluated by computer simulation.