Precise step length estimation (SLE) is a key necessity for not only navigation systems design but also gait health monitoring in neurological conditions. Among existing solutions, non-invasive inertial sensor-based approaches operating without dedicated infrastructure are more cost-effective. Many such methods, however, rely on bodily-affixed inertial sensors rather than freely held smartphone sensors. Traditional signal processing approaches, on the other hand, offer varying accuracy across diverse gait patterns due to user parameter calibration. This study, thus, proposes a regression-based SLE framework employing eight regression algorithms: linear regression (LR), k-nearest neighbours, support vector machine, decision tree, elastic network, random forest, histogram-based gradient boosting (HGB) regressor, and artificial neural network (ANN). Their extensive and rigorous evaluations across varied window sizes, using a dataset collected in normal and fast walking modes with two device positions (hand-held and trouser-pocket) during three evaluation scenarios, demonstrate the ANN’s exceptional generalization capacity over the other models and the previous method IRT-SD-SLE in unseen test evaluations with an achieved mean absolute error (MAE) not exceeding 6.3 cm. In seen test evaluations and leave-one-out cross-validation, the HGB regressor’s outstanding performance, achieving the lowest MAE below 1 cm across most contexts, is also reported. The extensive evaluations of training and testing times reveal the highest computational efficiency for LR, moderate efficiency for the HGB regressor, and the highest training cost for the ANN, indicating a clear trade-off between MAE and computational expense. Additionally, this study includes an insightful discussion on the performance results, including the trade-offs between accuracy and efficiency.