The FREEDM system is a technology for a smarter and resilient distribution system that facilitates a higher level of distributed energy resource (DER) integration by offering effective voltage regulation, reactive power compensation and real time monitoring and control. This paper provides a framework for conducting a cost-benefit analysis for such a smart distribution system. The method first identifies the benefits, and then quantifies and monetizes them. OpenDSS time-series based power flow simulation is used to quantify the benefits accurately. The costs associated with the new components of the system are estimated based on prototype units. A cost-benefit analysis is adopted to identify the scenarios where employing such a system by a utility becomes economically attractive.