Posting a picture will help. Ron

Thank you, Laura, Patricia and Glo! I do agree painting the trim the same as the house to blend in will help bring it more transitional than traditional. Great point! Will definitely be replacing deck railing to metal and front doors to something that brings in light. I love the frosted suggestion to keep privacy. By saying I want to keep the brick, I just don't want to replace it. I am open to painting it, but maybe that is a bad idea? I like to concept of dark charcoal, but the light brick looks a bit jarring against this. Should I look towards a lighter, or white palette for the exterior if I keep the brick as-is? If going with a darker palette, do I paint/wash the brick to be less contrasting? Also, I am still stuck on where I could add some natural cedar siding accents to bring in some nautral color/texture. Would I do this on the right entry wall, the entire entry cove, 270°?

I would keep the stone at the entrance but give it a new important appearance. There is a new technique where the grout lines are filled with new mortar up to the face of the stone to create a completely different more fresh & rustic appearance for the stone. I have also seen the filled grout lines with a lime wash over the stone to create a more even appearance. Here is the lime wash used on a stone wall to illustrate the Before & After. Here are options for your front door. I think the balance of your home could be painted or stained white. Or you can consider painting the shed design a gray value

Yes, the plants are a constant work in progress with the shade and the sloped yard and deer that devour everything. Once we got the pachysandra growing densely that helped. Deer don't touch the boxwoods. We have rhododendrons, but they are high since the deer trimmed off all the lower growth. We had some rot, but the painters brought a carpenter who replaced all the bad boards. We've also had to do control for wasps and ants. Keep ahead of the bugs. Figured out we had insects when the woodpecker started on the siding! When budget allows a more contemporary front door would be nice, plus change the light fixtures, and stucco the chimney.