Don't want to hijack, but torrey, I really like that color combo, considering for my house with brick on first floor. What line of BM exteriors would be best for this application?

You will need to remove the shutters for painting anyway so why not see how you like it without them. I would not paint the brick IMO it always lessens the value of a home.I like sage greens or grayed greens with brick and I think you could go quite a dark shade of that on the shingles.Then maybe beef up the trim insted of the shutters

I wanted to select a light stain like the shutters below, but they don't exactly work with your brick, so I selected a stain light than your current one with white trim.

Your home is Contemporary, but not Colonial by any definition. All of your evergreens have hit their 'sell by' date. They are overgrown covering your windows and cannot be trimmed into any viable shapes. Look at Superdeck.com for Their Duck Back stains for your home. Here is the color chart I would recommend you select a weathered driftwood stain for your home and possibly consider a corrugated metal roof for your home. To complement the new stain I would recommend the driveway be overlayed with a Chip or Macadam stone driveway. The contractor sprays some tar on the existing asphalt driveway spreads stone like a pea gravel and then rolls over the stone to press the new layer into the tar. I think it could be a handsome finish to your home.