I have a 2003 TTR 250 which seems to have an oil leak either from the "o" ring on the starter motor or somewhere close by. There also seems to have oil seeping out the grommet with 4 wires coming out of it, just in front of the front chain sprocket. Thank you Terry.
You may be lucky and you just need a new generator covergasket.
What is the history of the bike - have you had it for a while?
The reason I ask is that if the TTR has been run with a worn sprag clutch then it is possible for the "bang" on shut down to put so much pressure on the starter gears that it cracks the generator cover which then leaks when the engine is hot.