Background/Objectives: Western societies introduce school-based or school-linked programs in order to improve the physical health status of students and prevent the negative impact of the late diagnosis of a series of diseases and conditions. Preschool visual acuity (VA) screening represents an established school-based approach aimed at the early detection of amblyopia risk factors and vision-related learning difficulties. In this study, we report the methods and outcomes of the first officially organized kindergarten-based VA screening program in Greece, implemented using the Democritus Digital Visual Acuity Test (DDiVAT) screening suite and involving trained educators as part of the screening workflow. The present analysis focuses on the operational performance and screening outcomes within this defined setting. Methods: This study was a kindergarten-based screening. Each kindergarten was equipped with the DDiVAT screening framework, which consisted of a 32-inch, 4K, Android Smart TV with the DDiVAT application preinstalled, a site-license granting access to the secure DDiVAT database, and two vouchers for teachers to participate in the official lifelong DDiVAT training program. Results: From 2476 enrolled students, 207 (8.36%) were referred due to suboptimal presenting VA in one or both eyes. Average VA ranged from logMAR 0.11 to 0.07, which is consistent with former reports. Conclusions: No major technical difficulties were encountered, suggesting that DDiVAT may represent a feasible digital approach for preschool VA screening in real-world educational settings.