Studies addressing the supervised extraction of geospatial elements from aerial imagery with semantic segmentation operations (including road surface areas) commonly feature tile sizes varying from 256 × 256 pixels to 1024 × 1024 pixels with no overlap. Relevant geo-computing works in the field often comment on prediction errors that could be attributed to the effect of tile size (number of pixels or the amount of information in the processed image) or to the overlap levels between adjacent image tiles (caused by the absence of continuity information near the borders). This study provides further insights into the impact of tile overlaps and tile sizes on the performance of deep learning (DL) models trained for road extraction. In this work, three semantic segmentation architectures were trained on data from the SROADEX dataset (orthoimages and their binary road masks) that contains approximately 700 million pixels of the positive “Road” class for the road surface area extraction task. First, a statistical analysis is conducted on the performance metrics achieved on unseen testing data featuring around 18 million pixels of the positive class. The goal of this analysis was to study the difference in mean performance and the main and interaction effects of the fixed factors on the dependent variables. The statistical tests proved that the impact on performance was significant for the main effects and for the two-way interaction between tile size and tile overlap and between tile size and DL architecture, at a level of significance of 0.05. We provide further insights and trends in the predictions of the extensive qualitative analysis carried out with the predictions of the best models at each tile size. The results indicate that training the DL models on larger tile sizes with a small percentage of overlap delivers better road representations and that testing different combinations of model and tile sizes can help achieve a better extraction performance.