Black roof and brown trim looks a little odd.

I think that once the new windows are in it won't be too dark. Perhaps you can paint the very top edge of the roof trim with a darker brown/black as shown her. I'm sure it will be beautiful.

Slate blue trim!

I love Tudor style homes. I think making the light color darker, Like cafe au lait or caramel, would be nice. But it would be easier and cheaper to change trim and the blue CarrieHund suggests is lovely.

have they already been ordered? then let the roof be the odd man out.

On my monitor the trim looks like a softer gray-brown that doesn't look bad with the blue. In other words, it has some blue in it, unlike other, more chocolatey browns that lean more red.

Could you post the exact shade of brown that the windows will be?

Conceivably there could be some blue-browns for trim + body of the house that are somewhere between the brown of the windows and the blue of the roof that would tie everything together harmoniously.

Get the windows installed, paint or stain the front door a vibrant color, do some landscaping . . . then step back and take a look at the entire picture. Only then may you need to look into a different color for the half timbers and trim. I'm thinking that it will all come together in the end.

Hi, Megan--

Super-cute house. I think what stands out to me most is that the chimney is painted. Having a range of natural brick tones would add quite a bit of warmth that's expected in such a charming design. If the only part of your chimney that shows is what we can see, it wouldn't be difficult to sandblast the existing stack and restore it unpainted. That would go a long way toward warming this design back up and adding the right warmth that people love in half-timbered Tudor designs.

I think you're on the right track with the toned window sashes in your addition, but the other main player here will be softening up the front impression with landscaping. Defining some brick accents there, too - whether edging a new pathway or creating some raised flowerbeds next to the house - would also help add depth and texture to this design. Cheers!