Cute house. Yes, I would keep the stucco and I don't even like stucco! You have to use special paint for stucco to insure that the house still breathes after painting, otherwise the new paint can peel right off. I would paint it a cream or a pale taupe. It is hard to see the roof color. It might look nice with an earthy green trim color.
I would definitely get rid of the overgrown plantings. About the windows, instead of removing them, I would get storm windows. New windows, while energy efficient in the short term, almost always end up with broken seals. I've had storms on three houses and "new energy efficient" windows on two, and will never replace my old windows with new ones again. My current 1908 home has the original windows with storms and we love it.

Landscaping your cottage-looking house might include replacing some of the concrete with a brick walkway, a small tree towards the right corner of the house, and flowerbeds. Since we can't really see the whole property, I have to guess. You may want to add window boxes too.
Your house has great appeal and once spruced up, she will be even better!
Diane

It's a precious house! You are spot on with making the awning and foundation shrub removal a priority. They are just eating the house alive. LOL.

As said, try to retain the original windows if they are still in there. Not only for authenticity, but they'll outlast your new windows.

Again , ask a reputable contractor about painting stucco. Our old house is brick. It had been stuccoed over in the 1930s and believe it or not, that stucco job lasted until six years ago! My husband had had it painted before I married him and although it may have seemed like a cheap fix in the short term, it cost us dearly in the long run when we had it re-stuccoed.

We could not find a local company who did that type of work on two hundred year old, large homes. The stucco they applied is not the new stuff, but the same formula they'd have used in the 30s. The problem came because we'd painted. They said the new stucco would not adhere properly to the old because of the paint and it would eventually fail. So, the whole house was covered in what looked like chicken wire first. It added weeks to the job. And the whole crew of workers had to be transported almost two hours each way every day just to get here. Ouch.

I think you are going to have a lot of fun figuring out how you want this house to look. It is so unique and is going to be an eye-popper.

Keep the windows, get storms as mentioned above, and use spring bronze weatherstripping between the sashes/frames of the current windows. Save yourself tons of money and get improved efficiency!

I love the idea of keeping the windows. One of my biggest concerns had been what would happen to the trim on the inside if the windows had to come out. The stucco has never been painted, so that should help keep the costs of putting a new topcoat down.

My brother is coming up next weekend to help me start tearing things out. I'm really excited about how it's going to turn out.

Hope you post a pic when you get the shrubs and awnings removed. I bet it will make it look like a whole new house. I like the lines on the house, it's a nice one.