Trees provide numerous benefits for urban residents, including reduced energy usage, improved air quality, stormwater management, carbon sequestration, and increased property values. Quantifying these benefits can help justify the costs of planting trees; to that end, the U.S. Forest Service and Davey Resource Group created i-Tree Streets, a program that estimates the benefits provided by trees based on species and diameter at breast height (DBH). This presentation is the result of a 5-city study of trees planted by tree-planting nonprofits with neighborhood groups from 2009 to 2011. Tree size and survival were assessed in summer 2014 using the Planted Tree Re-inventory Protocol. We use this data to examine survival and growth rate of the trees and evaluate the current and projected benefits provided using i-Tree Streets. The re-inventoried trees currently provide almost $50,000 in annual benefits, the majority (75%) of which are increased property values. We also project the benefits of the trees by “growing” them to 40 years after planting and using i-Tree Streets to estimate the benefits of the grown trees. Some investigations into the model reveal that i-Tree Streets calculates benefits very differently between three climate regions and that there is an important distinction between annual benefits and cumulative benefits. i-Tree Streets is a useful tool for assessing the value of the urban forest, but these discoveries should be kept in mind when interpreting the output.