Hello Eric,
You can relatively very easily create a very accurate tree inventory with Global Mapper's Lidar Module. The State of Massachusetts has state wide coverage with Lidar which should be free to the city of Waltham to acquire. It is a relatively easy process to automatically classify trees and then extract them as 3D point styles with heights, spread and other information. From there you can easily export a table of data answering your question. We use ortho imagery in this process to add visual truth to this but it would be a relatively easy process to say test count the trees in a small radius like a park and then ground truth it by manually counting if you were really concerned about the validity. The data is hi-res enough that you could do that on a small area. We also have other tools for extracting the vegetation to DSM or DTM's to compare biomass stats and volume information.
If you need more info just let me know or download a free trial from our website of Global Mapper and then request an eval license for the base product and the lidar module. Happy Thanksgiving!
Best Regards,
Patrick Cunningham, President
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Blue Marble Geographics, 22 Carriage Lane, Hallowell, ME, 04347 U.S.A
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www.bluemarblegeo.com
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