Urban residential shade trees extenuate the heating of buildings in the summertime by intercepting insolation and by evapotranspirative cooling of their immediate surroundings. By modifying location-specific climate data, and tree growth characteristics, this research adapts the Sacramento Municipal Utility District’s (SMUD) Tree Benefits Estimator for application in Toronto, Canada. This tool is then put to use modeling the energy conservation savings delivered by 577 trees planted in Toronto backyards between 1997 and 2000. This study’s results estimate that the trees contributed 77,139 kWh of electricity savings as of 2009, 54.4% of which was due to shading of neighbouring houses. This study’s findings indicate that urban residential tree planting programs should not focus exclusively on location-driven strategic planting to yield large energy conservation benefits. Instead, it is argued that priority should be given to selecting planting locations that will maximize tree survival as neighbourhood energy conservation benefits of a tree that achieves mature stature often outweigh the homeowner-specific benefit of a strategically planted tree.