I would do a green on the shakes and leave the bricks alone.

I would get rid of the window boxes if you don't use them. Paint the trim and the sidelights of the entry white.

Is the roof color changing? I would remove the shutters and window boxes and stain the shakes dark charcoal. Paint garage door to match or replace it and match to the entryway door.

Yes we are changing the roof- would love advice on that too!

I think a charcoal or weathered wood would look good for your roof.

Here are some other possibilities.

Thanks so much!

Would suggest replacing the bow window if possible. There are far too many mullions and it detracts from your facade.

I would decide on the roof color before determining the color to paint the siding. The picture doesn't show your brick clearly but it looks as if there are some gray shades in some of the brick. A gray/brown shingle

Driftwood

or

Black Sable

would probably work with the brick and would also give you some options on paint colors. If you're interested in seeing some mock ups showing how different shingle and color combinations might look, check my website, Creative Visual Concepts.

Thanks! The brick has gray mortar although we are thinking of whitewashing it for an updated look. I like the black sable roof you posted!

I would go darker on the roof and less of the different colors together.
I love whitewash and think it’ll do wonders to the exterior

Thanks! We’re definitely leaning towards doing the whitewash and probably dark grey shingles with white shutters, or cream shingles with black shutters and a dark roof…
Do you guys think we should paint the front door a different color?

Assuming shingles you mean the siding? I would stay light.
Darker roof.
And you can leave the door color if you keep the actual door. If your buying a new one I’d get wood.
If you had to paint it a different color I’d go with a pretty blue.
But I feel like your more of a safe choices type :)

Yes I meant the siding 👍
We are keeping the front door- it’s actually stained a dark color wood. I am the safe choice type although I love blue!