Also redoing roof so we need to select a color for that as well

Start by selecting roofing (fewer choices there) to work with the brick. Paint comes in a gazillion colors and can be custom blended to work with those "fixed" items. Remove the shutters, and when you replace the siding, remove the aprons under the windows (and above the lower ones) so your siding can cover that area to be consistent. I don't think the faux colonial pediment trim around your door is era appropriate. Remove that and perhaps totally change the door, using a solid glass storm. Do you need protection from the weather at the door? You'll want to enlarge and upgrade the lantern light. And then its on to the landscaping. Cleaning up that tree on the left would help. If you decide to do something about the brick, that would come first. Check out Romabio for masonry paint/stain/washes.

first thing I'd do is remove the colonial accent around the door.

since you're getting new siding, pick something that works w/the brick (could be a navy, white, charcoal, gray, etc)

here's what the darker charcoal and roof look like. I don't care for the shutters all that much. and I think a double door would have look better here. but I like the transom window above it. you could do that.

for the roof I'd do a medium gray/charcoal. that roof goes w/any color.

you don't have a lot of brick. look at Romabio Masonry. it's a lime coating for bricks. very easy to apply and no maintenance.

here are some similar style homes to give you ideas.

I believe the paint color on this one Iron Mountain. looks great w/the dark windows and roof

and if you really want to take it to another level:

gray brick, lighter gray siding, new landscaping w/path, and a very large portico over the front door area. you could size this down a bit.

check out this link to see how they modernized their split level

https://www.fourgenerationsoneroof.com/how-to-modernize-a-split-level-home-with-black-windows/

Thank you both! Yea for sure the colonial piece above the door has to go. Barf. I love craftsman design, and mid century, so a decesion needs to be made which direction to go for the door. Most likely craftsman, sidelights and transom above door.

We are thinking a weathered wood color from GAF for the roof.

We do live in Minnesota so a storm door will need to happen.

We live either sticking with white, a gray, or a blue or green gray. Decisions aren’t easy for us 🤣🤪 and this one is especially challenging since design doesn’t come easy for us either!

I've removed the shutters and the overly decorative pediment around the door. This color scheme might work for your home

If you like the mcm look, I'd do some composite wood siding (it looks like real wood) all around the door, paint the brick a dark charcoal, do a gray siding, darker black roof color.

or, paint the brick white, do a navy siding, weathered wood roof, but still do the wood around the door

basically like this. (i know it's a diff style. just look at the wood around the door)

get more of a modern pendant light

modern address,

and a more modern door. (you can remove the storm door during the summer, yes? )

or, do the composite wood siding across the front, paint the brick, black roof. for the siding on the sides, do a charcoal color

this is a wonderfully updated split level.

thanks everyone. We are definitely open to painting the brick. I think would love to go wood-finish composite front entry with side lights and transom, and all windows will be white as we are not replacing the upper windows.