Castanea sativa plays a key role in different production chains (timber, flour, honey, and tannins). Moreover, considering the great importance of chestnuts and chestnut flour for the food industry and for the subsistence of piedmont communities, a relaunch of this production chain is definitely essential, thus motivating this review. The first aim of this literature overview is to summarize current knowledge regarding the main criticalities in chestnut tree cultivation, chestnut processing, and in chestnut flour production. The second aim is to suggest specific improvement strategies to contrast the main pests and diseases affecting chestnut trees, improve chestnut processing and flour production, and, finally, valorize all by-products generated by this production chain. With respect to chestnut trees, it is essential to develop specific integrated strategies based on early detection and management to contrast known and emerging issues. With regard to chestnut drying and flour production, particular attention needs to be paid to molds and mycotoxins which definitely represent the main criticalities. In addition, further investigations are needed to improve the dying process in both traditional and modern dry kilns, and to develop innovative drying processes. Finally, to face the monumental challenge of environmental sustainability, the valorization of the whole chestnut by-products is crucial. This review clearly highlighted that the recovery of polyphenols from chestnut by-products is the most interesting, sustainable, and profitable strategy. However, the fungal fermentation or the incorporation of little amounts of these by-products into foods seems a very interesting alternative.