Urban fragmentation represents one of the major challenges affecting post-socialist residential neighborhoods, generating underutilized spaces characterized by ecological degradation and reduced spatial cohesion. This study investigates the potential of ornamental and aromatic plants to support the regeneration of apartment courtyard spaces and their integration into urban green infrastructure systems through the evaluation of a proposed landscape design scenario. A comparative approach was employed, combining Space Syntax analysis, expert-based ecological assessment, and perceptual–visual evaluation to compare the existing site conditions with the proposed landscape design scenario in a post-socialist residential neighborhood in Craiova, Romania. Spatial configuration was assessed using the indicators of integration, connectivity, and mean depth, while ecological and perceptual performance were evaluated through biodiversity-related indicators and the Scenic Beauty Estimation (SBE) method based on expert assessments. The proposed intervention, founded on a stratified composition of ornamental and aromatic vegetation, reduced impervious surfaces and was associated with improvements in spatial permeability, biodiversity potential, and the visual quality of the landscape. Space Syntax analysis indicated an increase in configurational performance (ΔC ≈ +41.6%), while perceptual evaluation showed higher mean expert ratings for aesthetic, functional, and sustainability attributes in the proposed design scenario compared with the existing conditions. These findings suggest that, within the limits of this case study and the applied evaluation framework, small-scale green interventions based on ornamental and aromatic plants may contribute to improving the ecological and spatial performance of fragmented urban spaces and provide a methodological framework for assessing similar regeneration projects in post-socialist residential contexts.