Much of forest science is dependent on accurate stem measurements, and relatively new photogrammetric techniques may be suitable for modeling stems from the terrestrial perspective. From imagery taken along a windbreak and urban roadways we tested the viability of photogrammetric modeling for producing accurate diameter at breast height measurements. Treatments for different point cloud models differed based on intervals between control points (i.e., every 5 m, 10 m, 25 m, and an absence of target control points) and site conditions (i.e., urban mixed species vs. a windbreak of Pinus taeda) over 100 m sections in the Tampa Bay, FL area. Stem diameter measurements from both the windbreak (n = 53) and the urban sites (n = 93) showed high conformity between field-derived and point cloud model measurements (linear regression showed R2values >0.9 and RMSE values ranging from 7.04 − 12.35%) with the number of control point targets having little influence on modeled DBH accuracy. Modeled stems of larger trees had greater associated error relative to DBH tape measurements, which can be attributed, in part, to problems with estimating diameter from non-circular stems of certain urban species (i.e., Quercus virginiana). Future work will focus on georeferencing these datasets and extracting data on other aspects of stem biometry (e.g., lean angle of stem, stem volume, etc.).