Cities and nations worldwide are pledging to energy and carbon neutral objectives that imply a huge contribution from buildings. High-performance targets, either zero energy or zero carbon, are typically difficult to be reached by single buildings, but groups of properly-managed buildings might reach these ambitious goals. For this purpose we need tools and experiences to model, monitor, manage and optimize buildings and their neighborhood-level systems. The paper describes the activities pursued for the deployment of an advanced energy management system for a multi-carrier energy grid of an existing neighborhood in the area of Milan. The activities included: (i) development of a detailed monitoring plan, (ii) deployment of the monitoring plan, (iii) development of a virtual model of the neighborhood and simulation of the energy performance. Comparisons against early-stage energy monitoring data proved promising and the generation system showed high efficiency (EER equal to 5.84), to be further exploited.