The objective of the present work was to categorize the risks in the on-farm welfare of dairy sheep in semi-extensive systems in order to highlight if risks in welfare vary according to the farm size. To the best of our knowledge, this study constitutes one of the few categorizations of the risks in the welfare of dairy sheep reared semi-extensively. The survey was conducted on 12 semi-extensive dairy sheep farms in Tuscany (Central Italy), which were classified according to flock size: <500, from 500 to 1000, and >1000. The results showed an adequate rating for all the farms included in the study. The most critical issues concerned the ratio between the number of stockpersons and the number of animals within the farms, the small decubitus areas, the lack of udder cleaning procedures during milking operations, and, in terms of biosecurity, the lack of prevention, control, and eradication plans for the most important infectious ovine diseases. The results show that different items in the five areas evaluated, including the assessments of management of the flock, the number of daily inspections, and the hygiene of the water supplies are associated with the farm size. In large farms, the assessment of management of the flock was better, but the number of daily inspections and the hygiene of the water supplies were worse.