The Energy Performance of Buildings Directive introduced the Smart Readiness Indicator (SRI), a common European system for assessing buildings’ smart readiness. While not mandatory across the European Union, some countries have initiated trial phases, and several studies already examined its application in different Member States. In this work, we present the findings of an extensive application of the SRI methodology on a sample of 59 recently constructed or recently renovated high-performance buildings in South Tyrol, Italy. Our research focused on two main objectives: (1) characterizing the level of smart readiness of state-of-the-art modern buildings in the Italian Alpine region of South Tyrol, and (2) discussing the potential correlation between the level of smart readiness and building energy performance class. Specifically, the HVAC and building systems with the most widespread adoption of advanced smart technologies were identified, as well as those configurations with traditional control solutions suggesting potential for improvement. The analysis proved that the different building categories present various levels of smart readiness, which is higher for the local office buildings and lower for the residential ones. No particular correlation was found between smart readiness and energy performance class, suggesting the need of adopting the SRI to give a more comprehensive characterization of the building performances.