Because the houses are close together I would be mindful of the houses on each side. These colors are from this website: Foundry 7 Inch Perfection Shingles from VinylShake.com The dormer should be the same as the rest of the house

Snow

Biscuit

Shadow

Jumiper

Thanks for the comments. I think I like the snow colour. I tend to like the grey tones better than the brown ones to be honest.

Take a look under the siding you want to remove. The original is probably underneath and likely restorable. Most vinyl and aluminum siding was put on just to avoid painting. My guess is the original is the most appropriate shape, side and material.

That’s a good point actually- it is cedar shingles at least in some places (so likely all of it). That said, there are loads of coats of paint on the shingles since the house is very old. I guess when I tear it off I can check and see

here are some ideas you could implement

you could always do something diff in the gable portion. either a slat wood, cedar shake, shingle, etc.

perhaps look into adding a portico and redoing the steps?

use your imagination w/this pic. simple vertical board/batten siding

or you could do the upper half in the vertical (or a cedar shake) and the lower portion like shown here

maybe add on a porch w/that portion covered w/roof.

I wouldn't suggest using a real wood door unless you have some type of overhead protection.

Some option with color

or

Wow, there are some excellent responses here- thank you all!

I like the idea of vertical batten board and a porch of sorts- I was thinking so doing a small porch anyway so the overhead could definitely improve the look of the house. Understood on not using a real wood door without cover- to be honest I would probably go for a wood look door provided I could find one I like.

The house looks much different in those colour shots! I think I like the darker one more, but that may just be because it’s so different to the current colour. Either that or going with a white, provided I power wash it enough.

I really like the Juniper as shown above. I think that gray is very overdone. I would add a portico and change the metal railings to white vinyl or wood.

Understood on redoing the stairs, and ideally since it’s not large I would rip that and the flowerbed out and make a porch of sorts where the stairs are sideways (I.e. you walk from the car over the existing flowerbed then up the stairs).

I love the portico idea, but my house is only 5 feet off the curb on one side. I’d have to check the local code to see how close I can get.

I guess if there is a look that I like, here are a few photos that epitomize it after reviewing everything posted above. I think I like white just given that it's pretty simple and I won't tire of it, and the board and batten look seems to work for me. I think I'd do (white) vinyl cedar shakes on the side and back though, just for textual contrast.

It would mean that I'm potentially tied to getting new front windows, but that's not necessarily terrible. I am planning to build a large wired shed for flex space in the backyard and the look I already liked is below (third picture). If I did the house this way it would tie in nicely with the shed, and I could reuse the big window in the front of the house on the shed as I'm certainly not getting those beautiful accordion doors. I would also accept white on white for the shed in terms of windows.

Denver Urban Craftsman Bungalow Pop-top | Board and Batten · More Info

Urban Farmhouse · More Info

Shed design I like

Current backyard. The existing shed and tree would be removed, and the hedges need an aggressive pruning.

White with both vertical and horizontal siding will be interesting but not more work. Cedar shakes up high still need to be taken care of. The simpler, the better. That gives you choices on door color and when you change the windows, you can do black trim. Yes, you need to know if you can extend an overhang, porch and walkway. I like your idea of being able to walk from the driveway to the house. Your home is adorable. It just needs a little love.