That's a lot of red, which is why it's probably two-toned now. Have you thought about other colors that go well with a red roof and chimey:

Henderson Road Farmhouse · More Info

Meander Road · More Info

Note cedar stain on pergola. Consider staining your porch a reddish cedar.

Sears House Garage Addition, Camano Island WA · More Info

Garage and Entry · More Info

Do a Houzz, Pinterest, and Goggle search for "Red roof craftsman" A search will give you some options you might not have considered.) Great house!

Two toned was done frequently on this style of house, although I've seen green on the top half more often. The red roof kind of limits you. Will you be replacing the roof too? If you do red, I would keep it to the top half. Just please don't do gray - that era of house was never painted gray. Craftsman bungalow colors are earthy. You can always do cream all over - just not a white-white.

Craftsman style, side-gabled and with the front gable dormer and a full porch.

Working with the red roof, have the darker paint color abut it.

Thank you all! Realized I didn't pick the best photo... The evening light makes the roof look red. Here's one in a better light.

Love the house!!! I would do a soft, sage green on top, and then have some fun on the porch with coordinating colors and a bright front door.

So the roof is gray? Crisp white house, red door.

Does the white section of the siding even need replacing? If not, spend your budget on power washing the roof, fixing the porch with red brick and gray cement front steps and walkway,

I’ve seen one with green at the top.

I would focus on fixing the mess of a porch first. Craftsman columns, new skirting, new stairs.