David,
I had the same issue on my 281. On a call w/ Lewmar, here's what tried based on their feedback:
The "old" Lewmar standard portlight has a two piece aluminum frame.. There is a rubber gasket that links the two parts. That gasket breaks down and starts to leak. The fix suggested was to scrape a small amount of that gasket out from the outside with a razor blade. (I tried this on one to start.) I scraped/cut our a very thin layer of this - likely 1/32" ~ 1/16" but no more. You then take silicone (clear) sealant and put a bead of it on that joint, slightly overlapping the aluminum. Do this on both sides of the joint. For me, no more leak. I also replaced (previously) the window seal that goes fully around the window in the frame, as well as the O rings. I kept all greased with a clear silicone based grease. annually.
This worked well for me. When i bought the boat, all leaked. when i sold it, no more leaks !
I miss my 281. it is a great boat.
Tim