Cities are the keystone landscape features for achieving sustainability locally, regionally, and globally. With the increasing impacts of urban expansion eminent, policymakers have encouraged researchers to advance or invent methods for managing coupled human–environmental systems associated with local and regional sustainable development planning. Although progress has been made, there remains no universal instrument for attaining sustainability on neither regional nor local planning scales. Previous sustainable urbanization studies have revealed that landscape configuration metrics can supplement other measures of urban well-being, yet few have been included in public data dashboards or contrasted against local well-being indicators. To advance this sector of sustainable development planning, this study had three main intentions: (1) to produce a foundational suite of landscape ecology metrics from the 2007 land cover dataset for the City of Toronto; (2) to visualize and interpret spatial patterns of neighborhood streetscape patch cohesion index (COHESION), Shannon’s diversity index (SHDI), and four Wellbeing Toronto indicators across the 140 Toronto neighborhoods; (3) to quantitatively assess the global collinearity and local explanatory power of the well-being and landscape measures showcased in this study. One-hundred-and-thirty landscape ecology metrics were computed: 18 class configuration metrics across seven land cover categories and four landscape diversity metrics. Anselin Moran’s I-test was used to illustrate significant spatial patterns of well-being and landscape indicators; Pearson’s correlation and conditional autoregressive (CAR) statistics were used to evaluate relationships between them. Spatial “hot-spots” and/or “cold-spots” were found in all streetscape variables. Among other interesting results, Walk Score® was negatively related to both tree canopy and grass/shrub connectedness, signifying its lack of consideration for the quality of ecosystem services and environmental public health—and subsequently happiness—during its proximity assessment of socioeconomic amenities. In sum, landscape ecology metrics can provide cost-effective ecological integrity addendum to existing and future urban resilience, sustainable development, and well-being monitoring programs.