An increasing number of aircraft is equipped with wing tip devices, which either are installed by the aircraft manufacturer at the production line or are retrofitted after the delivery of the aircraft to its operator. The installation of wing tip devices has not been a popular choice for regional turboprop aircraft, and the novelty of the current study is to investigate the feasibility of retrofitting the British Aerospace (BAe) Jetstream 31 with an appropriate wing tip device (or winglet) to increase its cruise range performance, taking also into account the aerodynamic and structural impact of the implementation. An aircraft model has been developed, and the simulated optimal winglet design achieved a 2.38% increase of the maximum range by reducing the total drag by 1.19% at a mass penalty of 3.25%, as compared with the baseline aircraft configuration. Other designs were found to be more effective in reducing the total drag, but the structural reinforcement required for their implementation outweighed the achieved performance improvements. Since successful winglet retrofit programs for typical short to medium-range narrow-body aircraft report even more than 3% of block fuel improvements, undertaking the project of installing an optimal winglet design to the BAe Jetstream 31 should also consider a direct operating cost (DOC) assessment on top of the aerodynamic and structural aspects of the retrofit.