Have you chosen a manufacturer and product line for the shingles? If so, then you know which colors you're choosing from and people are in a better position to make suggestions. Post a picture of the sample board from the roofer. In general I would say you want a color that is less brown and a little darker than what you have now. I don't care for the almost black as shown in your last picture, but some people like that look. Roofs last a long time, so you have to ask yourself if you'll still like it after the fad for black roofs passes.

As far as the gutters and downspouts, you want them to blend in to the exterior as they are not architectural elements to be emphasized. That's why the HOA wants you to use earth tones. It looks like they currently match your siding. If that's true, leave them alone. They look a little off with your brick, but if the siding is staying the same I don't think they can be changed. Remove the shutters from the frontmost window. They look out of place.

I would choose a charcoal colored roof, and make it solid color, rather than variegated shades of charcoal, so, it does not clash with the busyness of your brick.

I would choose a gray roof, paint the siding similar and ditch the shutters.

"We will be getting a new roof soon..."

• Energy Star Cool Roofs
• Cool Roof Rating Council - What is a Cool Roof?
• Roof Directory

These are the samples they gave me.

Names

Surprisingly, the TruDefinition Duration® COOL Plus Midnight performs well as a cool roof. Mystic Gray is also a good performer.

You can browse the Owens Corning Duration shingles sorted by solar reflectance in the Cool Roof Directory.

The designer collection is crazy. Estate Gray looks good. Have the contractor bring you a large piece to try on the roof so you can see what it will look like. It's a big investment and you want to love it. Also take the shutters off.

"Estate Gray looks good"

TruDefinition Duration FLEX Estate Gray looks nearly identical to cool roof TruDefinition Duration COOL Plus Mystic Gray so I'd choose the latter unless there were something compelling about the Flex product.

Sand Dune would blend the best. You may prefer more contrast, though. If so, go with a dark brown:

• Summer Harvest
• Driftwood
• Peppercorn
• Teak

Whatever you think you like best, get a bundle or "square" to test first. Don't make a huge investment like that without loving it!

You could always go with "Dark Earth" or a topsoil color (also known as "Dark Bronze" or "Musket Brown" as the gutter color--it doesn't get more "earth tone" than that! And, yes, gutters can be used as an accent color if done properly. Think: trim.

(BTW, as others have stated, remove the front shutters and paint the window trim to match all the other window trims.)