Global market developments of wooden pellets have led to an increased attention towards pellet quality. ISO 17829 defines the procedure to assess pellets’ geometrical parameters, which play a key role in pellet overall quality. For instance, pellet length influences the spatial arrangement within the stove brazier, affecting the interaction between combustion air and solid biofuel, thus affecting CO emissions. The ISO 17829 method is time-consuming and affected by the operator’s accuracy. Recent studies have investigated the application of new methods, such as image processing, for monitoring the aforementioned parameter. While also assessing the representativeness of ISO 17829’s method, this paper proposes an alternative measuring tool based on image processing named Pellet Length Detector (PLD). Samples were obtained from Italian pellet suppliers and subjected to a multiple dimensional analysis via PLD and caliper. The PLD’s overall performance led to satisfactory results, with only 10% of the samples having a bias between replicates of >2 mm. Compared to caliper, PLD led to an average bias of 0.5 mm. Moreover, a one-way ANOVA highlighted that increasing the sample size between caliper and PLD leads to a greater statistical similarity of the data obtained for different replicates. Given the prototype status of the device, a further performance upgrade is possible, especially through error modeling.