District heating and cooling systems represent a great pillar of European cities aiming to achieve climate neutrality. This study investigates stakeholders’ perspectives on district heating and cooling to analyze the challenges, barriers, and potential accelerators of a sustainable low-carbon energy transition in urban areas. This study was performed via a survey-based approach, targeting multi-level stakeholders, both from the supply and demand side. This study employed a structural methodology involving customized surveys tailored to different stakeholder groups, aiming to understand challenges, advancement, and opportunities in Romania’s district heating systems. The results highlighted the diverse interests of stakeholders, emphasizing the need for financial support to reduce reliance on fossil fuels from the supply side while addressing concerns about infrastructure and current operations from the demand side. This study laid the groundwork for shaping national and regional policies and promoting local partnerships to reduce fossil energy demand and support the transition to renewable energy sources. Using a multi-stakeholder, cross-sectorial approach, and SWOT analysis in Romania, it systematically addresses technical, financial, and regulatory challenges for the greater sustainability of these systems in the urban environment.