John Deere 318 and 420 garden tractors actually had a sight glass to show oil level attached to the back of the rear end/transmission housing. The oil levels would rise once the oil was warmed up because the more viscous oil returned to the transmission faster. Even that was slow to show level increases as oil was added. I always worried about cracking the level tube or breaking the 3/16 plastic hose which ran to it, but it never happened.
In your situation, I think that you probably put in a lot of oil fairly fast, and checked the level right away. I think if you had filled a bit more slowly, and not to the top, but to the bottom of the dipstick and then waited 10-15 minutes to check for a final level, the dipstick might have read more accurately. Also , running the engine and warming the oil up, once you were close to the minimum mark, and then stopping and checking the level would be the way to do it.
At least now you know that your particular design tractor is slow to show oil added to the trans casing. You know, in future, to fill slowly and not try to go to full mark and pause 10 or 15 minutes to check level before you top it off. There should not be any surprises for you from now on.