Far cheaper to repaint rather than re-shingle.

A shingle-style house should blend with its surroundings, so yellow would be a bit strong--think more earthy, like ochre or a amber-yellow. Green was also a popular color for that style, dark sage or olive would be nice.

Check out Roger Moss' Victorian Exterior Decoration for color schemes and four major paint companies choices in appropriate colors.

Hey Columbusguy1, were in agreement again.

Originally the house would have been covered in unfinished shakes, or at the most, stained and oiled - so a color that reproduces the worn color of wood is perfect.

Please dont paint it yellow - its not a colonial house (which are, really, the only houses that can carry off yellow). Instead look at ochres or dull warm grays (which is the color of weathered cedar, anyway) - both of these are light colors. BUT, having said that, I think the house looks amazing in deep brown.

The brown is way too dark. It makes the home look foreboding. What part of the palate would I be looking for to have a lighter color?

When I replace the shingles I was thinking about white cedar dipped in sickens. I really like the look of Nantucket style homes.

Nice house you have there.
I note you say "WHEN I replace the shingles...." so I guess you will sooner or later, but you are proposing a paint job in the time being?

Just so you don't make BIG mistakes, I suggest you buy yourself some new shingles and set about painting them, or doing the Sikkens thing to them. Even painting some of the old ones behind shrubbery where they do not show could give you a way to eliminate some of your proposed colors. And I absolutely LOVE ochre. It is the earthy version of the yellow you are proposing, and can be dark or light. It does not show as much texture as the Nantucket cedar shingles that you say you love so much.

But if you get a good painter, tell him you want to "antique" your brown house, by putting a nice light color over that dark brown, really ragging a dull warm gray over the textured shingles, letting some of the brown show through like the older weathered homes seem to show. Now that could be done on a patch behind the shrubbery too, just to check it out.

It might give you a new feeling about your house, and let you enjoy it a few years more before re-shingling.

No house should ever be painted white, especially an old one with so much mass to it--it will be a glaring monstrosity to anyone who sees it, and will never go with anything around it.

With the stone on the lower parts, pick a color similar to those, and you can't go far wrong...that house screams for an earthy color, be it light, medium or dark...white will only make it look alien to the landscape. AND you would lose all detail of the trim....

If the shingles are in good shape, why replace them? Modern woods are NOT of the same quality--they will not stand up as long as the ones already there.

I think your shingles are perfect - it's the roof color &/or material that looks off. I can't tell which from the photo.

Even though I like your roof and shingle colors, I see why you think it is too dark. It is a lot of brown. I would look at either some mossy greens or a tan leather color. In the Benjamin Moore line, colors like Cedar Path, Great Barrington Green, Forest Hill Green, Copacubana, and Morgan Hill Gold. Your roof is a prominent feature of your house so the shingle color has to compliment that.
Diane

The matching the stone idea is a really good one. I just learned the shingles are only 10 years old. I think we will wind up with something lighter in the gray family. Also a good idea to try painting a bit to pick what we really like.

Now on the antiquing idea before, does that just mean painting without a primer over the existing shingles?

Just had to say "charming house indeed!". What a gem.
I'll dissent on the gray idea. Somehow I don't see gray playing very well with your very brown roof. Taupe maybe? Or, as Diane suggested a leather tan or mossy green, would seem good to me. But, then, I'm a huge fan of green! Best of luck and DO let us know what you end up doing in the end! Cheers, -Kim