Globally Important Agricultural Heritage Systems (GIAHS) territories are highly relevant to achieving sustainable lifestyles with human subsistence in balance with the ecosystem. The Barroso agro-sylvo-pastoral system is a clear example of this alignment between existing society, nature and natural resources, the environment, landscapes, and contextual heritage. Moreover, the sustainable use of existing natural resources, excellent environmental conditions, and breath-taking untouched landscapes represent a truly relevant factor towards the development of a region economy that is still greatly influenced by an engraved cultural, patrimonial, and agricultural heritage. Given the GIAHS classification attributed to that territory, the need arises to guarantee the existing environmental conditions. This context will allow the maintenance of the GIAHS classification, ensuring the quality of life in the region and stimulating its socio-economic development and overall sustainability. The present article describes a proposal for a digital ecosystem model aimed at the Barroso GIAHS, composed of four main functional hubs that actively interact with each other: smart environment, smart government, smart economy, and smart people. Based on wireless sensor networks, IoT, artificial intelligence, data analytics, and other technological solutions, this solution will allow real-time control of the territory’s environmental conditions and develop more efficient and well-supported management and governance.