I'm guessing that you are stating temperature being relatively constant at 50 degrees F, as in fall weather. That means the water is colder as well.
I am going to hypostulate some things related to heat.... mostly expansion of cast parts. You may have a hairline crack in the block between the cooling jacket and the oil gallery. If the engine is running cold, then water would seep in through the crack and contaminate the oil. Usually small block chevy cracks outward, around number 4 cylinder near the deck, but it depends. Cracked blocks are VERY common on old engines in a marine situation, and because the water pressure through the cooling system is not very high, like a closed system, the crack goes unnoticed. The other problem could be a head gasket, that is leaking in one place, again, only because the engine is running cool. When engine runs a little hotter internally due to higher water temperatures, the crack or gasket seals up... at least enough to mask any small amount of water getting through.
What your temp gauge says, and what is happening inside the engine is somewhat different, since the temp gauge is the average temperature of the water running by the sending unit. Oil runs hotter, and water runs hotter, depending on where it is in the system. The thermostats on 283F and 327F are 160F if memory serves, and they may be worn out too. Having the temp gauge calibrated and restored, along with a new sending unit, is a useful exercise.
My two best guesses. Both of these are pretty hard to diagnose completely without taking the engine apart, but it is possible. You can do a leakdown pressure test of each cylinder to determine if there is a crack, but you can also get leakdown from valve seats if the engine has some hours on it. You can look very very carefully at the outside of the block to see if there is evidence of cracking on the outside but beyond that, you are committed to tearing an engine down and magnafluxing things.
If this 327 is original and has never been rebuilt... well...
What year is the boat and engine? Has it ever been rebuilt?