In recent years, public authorities around the world have used incentive strategies to encourage the renovation of the existing building stock to meet the set carbon neutrality targets. However, the design of the incentives typically does not consider that the subsidized energy efficiency measures should result in robust long-term improvements with respect to various objectives. Moreover, building energy retrofit analyses are commonly conducted at the individual building level rather than at urban scale, which could instead significantly accelerate the renovation rate. In this context, the current research aims to combine these different factors to support the design of building energy retrofit programs. We developed 21 subsidization strategies and their impact was evaluated on a parametric multi-objective optimization with respect to energy, economic, and environmental performance for a district located in Bolzano, Northern Italy. The optimization was performed considering a set of energy efficiency measures, pertaining to building envelope, climate change, economic scenarios, and two types of energy supplies. The results showed that (1) the impact of climate change is limited for the climate of Bolzano; (2) the type of energy supply strongly influences the economic feasibility of the retrofit investments; (3) when the investment is profitable, the optimal solutions include those measures with the largest impact on energy efficiency; and (4) subsidization strategies modify the number and composition of the Pareto solutions.