[Baby Jane]
Why Maggie?
Nor do you see Lisa or Bart get older.
Perhaps all The Simpsons episodes are packed into a 1 year period.
This was the best rationale that I could have come up with when I came about the same though regarding their age. But to think, 300+ episodes doesn't exactly mean a years worth of events since within many episodes they display events that occur over more than one day. For example, Bart traveling to France or Homer seeing his mother for the first time in years.
It's just a running thing that I think works well with the simpsons just being the simpsons. However there were points when Bart and Lisa were in a grade lower than they have been shown to be ya kno'. =P