It looks as if the shakes are in bad shape so I would start with replacing them. You could do horizontal siding, shakes or board & batten. I would also remove the awning over the second floor window.

Are you planning on keeping the patio enclosure? I would also put wider trim around the windows that have narrower trim.

If you're interested in seeing some virtual makeovers with different sidings, colors, etc. check out my website, Creative Visual Concepts.

I would paint it fresh if possible to save shakes, if not, then replace them.

Thanks everyone. The house is from the 1930s. It needs a ton of work inside. I want to get rid of the patio enclosure, fyi.

I assume the shakes are what's on the roof. Would you build out the dormer or raise the roof?

Some options

Like these.Thanks. The shakes are the siding, I see.

Painting and getting rid of the enclosure would look better. I like the red. Is it time for a new roof? If so, get one in a more charcoal gray.

I would like a shed portico over the door.

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nice

thanks so much

Like the comment about the thinner trim.

I suppose it depends on budget. Paint in a lighter color would look nice, The options presented are quite lovely. Also, a white or lighter color would look nice as well. I realize this is siding, but it's a lovely color. Roof and trim color has to be considered to play into everything as well. It's a really cute place!