I like your home though the landscaping could use a more thoughtful plan. I don't think you're going to be able to change the pitch of the roof over the door, and I'm not sure that would add more light.

I think a greyish architectural shingle is the right selection for your roof and you could consider restaining the house a lighter color.

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I would open up porch entry walls and even maybe roof over door to let in more light. The use of natural wood with your exterior color will bring some much needed contrast. beefing up or just painting the existing window trim dark brownish black will give you big bang for the bucks. The chimney could also go dark for some architectural interest.

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following.

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I agree that a grayish architectural shingle would really enhance your look. Since you've recently painted, you may not be able to do that again right now, so I'd work with adding some contemporary looking sconces, painting the door a color, and using contemporary planters at the entrance. Also, removing the curtains in the front window to something more modern would be a nice look. I absolutely love your home!

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Add a couple of skylights to the porch roof so the front door can be appreciated. Or open the front part of the roof like a pergola for additional light.

Monotone equals monotonous appearance...all gray is all gray. Clean new roofing, a colored front door and trim, and color in the landscape will give a bright lift and good contrast, whether you keep the house gray or not.

I like your house. The only "problem" I see is the doorway is awfully dark. In addition to painting your front door a lighter color* (soft creamy buttercup yellow would look awesome with gray), what about adding some decorative lights? Such as, a string of white LED lights that you could leave on all the time (cheap enough to give it a try and see if you like it). Or side scones, as suggested above, that could be left on 24/7.

What I would *not* do is cut off your house's nose -- the length of the doorway roof balances the cut-out of the roof-line above it.

*edited to add: and use this same color on some sort of accent on each entry side wall. A decorative stencil? Molding strips to suggest a rectangular panel? A small mirror and shelf? Just something to bring a touch of light color to the side walls.