I think a softer weathered grey shingle would look nice. But I would remove the shutters around the windows that are wider, and the shutters don't look like they would close. I think black would be too heavy. Once the roof is settled, you can think paint.

I would not introduce grey into a palette of off white/tan. Unless I was planning to change the off white/tan color.

Shutters do not work for these windows.

Wow, it didn't even occur to me to remove the shutters. Thank you for that perspective. I LOVE window boxes, so I can look into that for sure. We are 100% changing the landscaping (it's horrible!) but trying to deal with paint also. We also want to upgrade the front steps (and you know, add a 2nd railing), but trying to do the painting first. Thanks for helping me with my little ugly house. :)

Agree with removing the shutters. They're almost never right for double windows. I think tan, black and white would work nicely. It's a very popular color combination in our area. As simplechoices suggested, a wide white trim around the windows would be good. You could paint the door a shiny black. A previous home of ours had tan siding, slate blue shutters/door and white trim...similar to simplechoice's last photo. We also had a very long slate blue window box in front.

This is similar to what I was thinking with the tan, black and white. However, no shutters in your case but maybe black window boxes. Also, a black door instead of the red. You mentioned the landscaping being changed. That will add a lot.

Love your pumpkins! :-)

I like your dark windows trim. With your roof you actually can go with any color you like . I like white/off-white or ivory.