Copernicus Sentinel-1 images are widely used for forest mapping and predicting forest growing stock volume (GSV) due to their accessibility. However, certain important aspects related to the use of Sentinel-1 time series have not been thoroughly explored in the literature. These include the impact of image time series length on prediction accuracy, the optimal feature selection approaches, and the best prediction methods. In this study, we conduct an in-depth exploration of the potential of long time series of Sentinel-1 SAR data to predict forest GSV and evaluate the temporal dynamics of the predictions using extensive reference data. Our boreal coniferous forests study site is located near the Hyytiälä forest station in central Finland and covers an area of 2500 km2 with nearly 17,000 stands. We considered several prediction approaches and fine-tuned them to predict GSV in various evaluation scenarios. Our analyses used 96 Sentinel-1 images acquired over three years. Different approaches for aggregating SAR images and choosing feature (predictor) variables were evaluated. Our results demonstrate a considerable decrease in the root mean squared errors (RMSEs) of GSV predictions as the number of images increases. While prediction accuracy using individual Sentinel-1 images varied from 85 to 91 m3/ha RMSE, prediction accuracy with combined images decreased to 75.6 m3/ha. Feature extraction and dimension reduction techniques facilitated the achievement of near-optimal prediction accuracy using only 8–10 images. Examined methods included radiometric contrast, mutual information, improved k-Nearest Neighbors, random forests selection, Lasso, and Wrapper approaches. Lasso was the most optimal, with RMSE reaching 77.1 m3/ha. Finally, we found that using assemblages of eight consecutive images resulted in the greatest accuracy in predicting GSV when initial acquisitions started between September and January.