Find a paint chip card that has the colors of the lightest, medium and darkest bricks. Use the lightest color for the siding and the darkest for shutters. A new pinkish white will be fine for the trim that is already white. Test your samples on foamcore board cut to the width of the shutters.

I'm not a fan of painting brick as it turns a no maintenance product into a long term maintenance issue. The brick seems to have more browns than grays in it but the roof is gray. You need to find a color that marries the two. Something in the taupe family would work. Also, a couple of other things. If you plan on keeping shutters I would switch to a wider shutter that is correctly sized for you windows. The current ones are too narrow. Also, the area without a railing in front of the door needs to have one installed. Building codes require them if the change in elevation is more than 30", which yours definitely is. If you're interested in seeing some virtual makeovers of your house check out my website, Creative Visual Concepts.

We painted some samples on the house and now we are leaning towards Sherwin Williams Backdrop on the body of the house. We like that it looks a little grayer than Warm Stone. We feel like we have to go with something at least that dark because the house is surrounded by trees that drop a ton of stuff on it, and we have the Georgia red clay to deal with, too. Now we are struggling with deciding what colors the garage doors, fascia and gutters should be. Should we use the window trim color (Morris Room Grey) or use the body color (Backdrop)? We have plans to replace the garage door and roof eventually, but we need to figure out what looks best for now until we can do that. All advice is welcome!

If you don't want windows on the right side of the house, you can just plant taller shrubs in that space. I don't like the two different shaped windows on the left side of the house in your rendering. If you're adding those horizontal rectangular windows in the bump out, then use the same shaped windows below on the garage. You can place them higher on the wall so people can't look into the garage to see if you're home.