Well I'm not going to help much, but you are not alone. My 2.5 y.o. DD seems to be up every night and once awake she can't get back to sleep for about 1.5 hrs. The time of it varies and she has her molars already so I have no clue why. She does go back to her bed and I tuck her in to sleep, then I sit in the glider in her room till she's asleep (that's our usual method for putting her to sleep). I keep feeling like I should work on her going back to sleep independently but it's so hard to when all you want is to get back to sleep! The glider has a recline function so I usually bring a blanket and snooze in there till she's asleep, then I go back to my bed. I realize this may not be helpful at all depending on what your sleep setup is like but I just wanted to share my method of coping with it.
Oh and DD naps for 1.5-2 hrs a day typically, we never skip a nap but the duration varies depending on how tired she is. I try to get her down for the nap earlier as opposed to later cause keeping them to 1.5 hrs seems to keep our wakeup to only one a night (rather than more, eek!).
I hope someone else may have helpful advice! I'm not looking forward to dealing with this when #2 arrives in the spring!
Just another thought, is he fussing or crying, or seems uncomfortable? If so I would think that the teething is definitely to blame. Would you consider some pain medication if that's the case?