Urbanization poses significant challenges to ecosystems, resources, and human well-being, necessitating sustainable planning. Urban vegetation, particularly trees, provides critical ecosystem services such as carbon sequestration, air quality improvement, and biodiversity conservation. Traditional tree assessments are resource-intensive and time-consuming. Recent advances in remote sensing, especially high-resolution multispectral imagery and object-based image analysis (OBIA), offer efficient alternatives for mapping urban vegetation. This study evaluates and compares the efficacy of Sentinel-2 and Pléiades satellite imagery in classifying tree species within historic urban parks in Rome—Villa Borghese, Villa Ada Savoia, and Villa Doria Pamphilj. Pléiades imagery demonstrated superior classification accuracy, achieving an overall accuracy (OA) of 89% and a Kappa index of 0.84 in Villa Ada Savoia, compared to Sentinel-2’s OA of 66% and Kappa index of 0.47. Specific tree species, such as Pinus pinea (Stone Pine), reached a user accuracy (UA) of 84% with Pléiades versus 53% with Sentinel-2. These insights underscore the potential of integrating high-resolution remote sensing data into urban forestry practices to support sustainable urban management and planning.