Integration and management of the flexibility of Demand Side Resources (DSR) in today’s energy systems plays a significant role in building up a sustainable society. However, the challenges of understanding, predicating and handling the uncertainties associated this subject to a great extent hamper its development. In this paper, an analytical framework based on a multi-portfolio setup in presence of a deregulated power market is proposed to address such challenges by adopting the thinking in modern portfolio theory (MPT). A Numerical example that targets on analyzing the risk and return for various flexibility pricing strategies are presented to illustrate some features of the framework.