My two cents is to begin by editing out every non historical element, like raised planters and pots. Keep it all simple so as not to distract from the building. And make sure you can store cars in the garage as even they detract.

Thanks kitesei2. Those cars are temporary and not ours. Maybe replace one with an old carriage?

Agree with kitasei. More is not more. LESS is more. And no to a fake carriage.

You have a very dignified, formal home and carriage house. Think formal, traditional, manicured.

Hopefully the trampoline isn’t yours.

Sadly, since it appears quite newly installed, I'd get rid of the too small and too fiddly rectangular bed.

The trampoline came with the house and I hate it, but awaiting something to replace it (pool?) or the grandkids will be unhappy.

I agree about the garden bed. It’s acting as a nursery right now but will go once we figure it all out.
Thanks to all of you. Your comments are well taken. Keep posting please, and I’ll post my end results as well.

Go for the swimming pool. A swimming pool and a big lawn...wow that would be perfect for the grandkids.