The increasing urbanization projected to reach 60% of the global population by 2030 needs innovative approaches to urban sustainability challenges. This study investigates the potential of vertical farming as a nature-based solution for urban regeneration in underutilized spaces, with a specific focus on the Magazzini Raccordati of Milano Centrale railway station. The research employs a multi-method qualitative approach integrating three complementary analytical frameworks: SWOT analysis to evaluate internal and external factors affecting implementation feasibility, stakeholder analysis utilizing a Power-Interest Matrix to identify key stakeholders and their relationships, and Ecosystem Services Evaluation to assess environmental and social benefits. Following a systematic assessment of four potential locations in Milan, the Magazzini Raccordati site was selected for its strategic position, accessibility, and potential for social and environmental impact. Three development scenarios were formulated and evaluated: (1) local production with educational programs focusing on community engagement and food security; (2) restaurant-based culinary education emphasizing gastronomic awareness and circular food systems; and (3) research and innovation hub advancing urban farming technologies through academic partnerships. Results demonstrate distinct trade-offs among scenarios: scenario 1 maximizes provisioning and cultural services, scenario 2 enhances cultural services while maintaining strong provisioning benefits, and scenario 3 optimizes supporting and regulating services. The study concludes that an integrated approach combining elements from all scenarios would best leverage the site’s potential while addressing urban regeneration needs. Future research would benefit from quantitative assessment methods such as Multi-Criteria Analysis or Cost-Benefit Analysis to further validate these findings.