The smart grid concept increases the observability and controllability of the distribution system, which creates conditions for bi-directional control of Distributed Energy Resources (DER). The high penetration of Renewable Energy Resources (RES) in the distribution grid may create technical problems (e.g., voltage problems, branch congestion) in both transmission and distribution systems. The flexibility from DER can be explored to minimize RES curtailment and increase its hosting capacity. This paper explores the use of the Monte Carlo Simulation to estimate the flexibility range of active and reactive power at the boundary nodes between transmission and distribution systems, considering the available flexibility at the distribution grid level (e.g., demand response, on-load tap changer transformers). The obtained results suggest the formulation of an optimization problem in order to overcome the limitations of the Monte Carlo Simulation, increasing the capability to find extreme points of the flexibility map and reducing the computational effort.