The residential heritage that was built during the great expansion of real estate after the Second World War has severe deficiencies in structural safety, fire resistance, energy efficiency, and accessibility and these cannot be solved with sustainable renovation measures. This study focuses on replacement interventions and promotes a management model that addresses three areas (technical, social, and economic) and it refers to the application of the circularity principle to the construction sector for the goal of climate neutrality by 2050. The final objective is to define a protocol—namely, the guidelines—to reference in a decision-making process that promotes urban regeneration by comparing demolition with reconstruction and renovation. The proposed methodology allows for the determination of suitable areas in Bologna for replacement and the joining of the municipal geodatabase with data from archival research on building permits in 1949–1965 by using GIS software. This digital archive can be implemented in a digital twin for an urban block, which can become a predictive tool for urban planning and the management of the whole life of a building. The main result is the characterization of urban blocks by identifying typical features belonging to specific building libraries that are validated with density analyses. These urban clusters and building archetypes can be used to assess targeted intervention measures by using specific tools, such as predictive maps and 3D city models.

Adapting outdated building stocks’ operations to meet current environmental and economic demands poses significant challenges that, to be faced, require a shift toward digitalization in the architecture, engineering, construction, and operation sectors. Digital tools capable of acquiring, structuring, sharing, processing, and visualizing built assets’ data in the form of knowledge need to be conceptualized and developed to inform asset managers in decision-making and strategic planning. This paper explores how building information modeling and building performance simulation technologies can be integrated into digital decision support systems (DSS) to make building data accessible and usable by non-digital expert operators through user-friendly services. The method followed to develop the digital DSS is illustrated and then demonstrated with a simulation-based application conducted on the heritage case study of the Faculty of Engineering in Bologna, Italy. The analysis allows insights into the building’s energy performance at the space and hour scale and explores its relationship with the planned occupancy through a data visualization approach. In addition, the conceptualization of the DSS within a digital twin vision lays the foundations for future extensions to other technologies and data, including, for example, live sensor measurements, occupant feedback, and forecasting algorithms.

Depopulation has become a significant issue for local culture and built heritage conservation of many European rural areas. In San Giovanni Lipioni, a province of Chieti (Italy), this phenomenon has increased to the point that, nowadays, there are only 150 inhabitants and no significant economic activities. In this regard, the present paper aims to describe the crucial role of nature-oriented tourism in an economic, social, and revitalization strategy; how digital tools can be used to map and create a territorial trail system between municipalities; and, finally, outline the operations necessary for reactivation. The proposed methodology consists of a first digital survey phase using GPS receivers and outdoor navigation apps. The second phase would create a web platform with a system of virtual itineraries between villages, named “The Golden Leaves Paths”. After that, the last phase concerns the creation of analysis factsheets to guide the maintenance of paths and the design of iconic signage with artistic illustrations based on the oak leaves leitmotif to be installed along the paths. A local social promotion association will employ the outcomes, technical drawings, and strategies to reactivate paths as an attractive element for nature-oriented tourism and create a digital platform to foster the village’s territorial and cultural heritage.

The Italian residential building stock consists of 12.2 million buildings, with 7.2 constructed post-World War II during the economic boom. These structures were designed without specific regulations for seismic safety, fire resistance, and energy efficiency, and today lies the current state of strong obsolescence. Therefore, energy refurbishment may not always be the best cost/benefit solution due to these intrinsic issues. Consequently, the transition to construction systems based on circular economy principles brings new opportunities and becomes key to proposing replacement interventions for this heritage. This paper presents a comparative GIS-based bottom-up approach to evaluate the lifecycle impact of residential building blocks, encompassing energy, environmental, and economic aspects. Two tools are introduced: one for measuring energy consumption and the other for quantifying the quantities of materials stored in buildings. This methodology permits comparing the new circular buildings and different refurbishment scenarios to identify the most suitable solution from an environmental impact and financial point of view. The application of a case study, a residential urban block in Bologna, built in 1945–1965, highlights how the demolition and reconstruction scenario based on circular economy principles presents the lowest environmental impacts and is economically competitive compared to standard deep renovation techniques.

Situated in the province of Chieti, Italy, San Giovanni Lipioni is a representative case of depopulation, mirroring the challenges numerous rural areas across Europe face. In this regard, the present paper describes the activities of a four-year research project in collaboration with a territorial promotion association and a local action group (LAG) aimed at fostering the sustainable development of the territory, focusing on nature-based tourism, digital-based communication and activation strategies, and the preservation of built heritage. A multidisciplinary approach is employed, delving into three distinct levels, as follows: (i) a comprehensive analysis of the built heritage and the tangible and intangible culture; (ii) the activation of the nature hiking trails between surrounding municipalities; and (iii) an exploration of digital communication strategies for tourism promotion and territorial reactivation.

Massive construction systems have always characterized traditional architecture and are currently the most prevalent, straightforward, and cost-effective in many Mediterranean countries. However, in recent years, the construction industry has gradually shifted towards using lightweight, dry construction techniques. This study aims to assess the effects on energy consumption, comfort levels, and environmental sustainability resulting from the adoption of five high-performance construction systems in a multi-family residential building: (i) reinforced concrete structure with low-transmittance thermal block infill; (ii) reinforced concrete structure with light-clay bricks and outer thermal insulation; (iii) steel frame; (iv) cross-laminated timber (CLT); (v) timber-steel hybrid structure. To achieve this goal, a multidisciplinary approach was employed, including the analysis of thermal parameters, the evaluation of indoor comfort through the adaptive model and Fanger’s PMV, and the quantification of environmental and economic impacts through life cycle assessment and life cycle cost applied in a long-term analysis (ranging from 30 to 100 years). The results highlight that heavyweight construction systems are the most effective in terms of comfort, cost, and long-term environmental impact (100 years), while lightweight construction systems generally have higher construction costs, provide lower short-term environmental impacts (30 years), and offer intermediate comfort depending on the thermal mass.