The Arctic sea ice cover seasonally evolves from large plates separated by long, linear leads in the winter to a mosaic of smaller sea ice floes in the summer. The interplay between physical and thermodynamic mechanisms during this process ultimately sets the observed sea ice floe size distribution (FSD), an important metric for characterizing the sea ice cover and assessing model performance. Historically, FSDs have been studied at fixed locations over short periods, leaving a gap in our understanding of the spatial and temporal evolution of the FSD at large scales. Here, we present a new framework for image segmentation, allowing the identification and labeling of individual ice floes in Moderate Resolution Imaging Spectroradiometer (MODIS) data. Using this algorithm, we automatically process and segment 4,861 images, identifying more than 9.4 million floes over 23 years. The extracted characteristics of the floes–including area, perimeter, and orientation–evolve throughout the spring and summer in the Beaufort Sea. We find seasonal patterns of decreasing mean floe area, increasing FSD power law slope, and more variability in the floe orientation as the summer progresses.