pdb and winpdb both seem to be missing this essential (to me) feature. I saw something suggesting WingIDE has it but I'd prefer a solution that is free, and if I do have to pay, I'd prefer to pay for something that is better than Wing.
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This reimplementation of the built-in pdb.py has watchpoints.
http://morepypy.blogspot.com/2008/06/pdb-and-rlcompleterng.html
I tried it but, in cursory tries was not able to get it to work.
Please look what pydev in eclipse offers...
You should check out Eric4
It's a very good Python IDE with a builtin debugger. The debugger has views for global variables, local variables and watchpoints.
Take a look at PyScripter. It has an integrated debugger, watch windows and much more. It's open source and is developed here.
HTH
It's too bad that the standard pdb module that comes with python itself does not yet support watchpoints.
Described here: http://wiki.python.org/moin/PdbImprovments