Have you thought about replacing the siding with cement board?

I think it depends on how much you want to do. Look at Certainteed Grand Manor to get some depth on your roof. If you want to really update the look think about replacing the stone with stacked stone. Here are some ideas.

Sorry to hear about the damage to your home but it does give you the great opportunity to update your home! You can do the various tones of beige and brown roof, classic white with charcoal roof, or even stick with green but just in a different shade with a grey roof. I really like the classic white but the different shade of green is very appealing.

I believe it is Sherwin Williams that allows you to upload photos and change the colors to the exterior if you wanted to play around with it.

Bellburgmaggie, I like the depth the roof material adds. I will certainly check that out. Thanks. I have been looking at some grays but the Rock is a stumbling block

Yes, I know the rock is a stumbling block, you have no idea how many roofing materials and paint samples I played with for 2 hours trying to get a good mix. One thought I had was simply to replace the chimney with stacked stone and to paint the stone at the base a darker color than the base of the house. On the roof issue, most people go with the cheapest roof - big mistake - why. Because the majority of the cost of your roof is the labor to install it. Check with your agent on the roofing materials which have the LOWEST claims in your area for hail, etc. Because you may save over the next 5 years the extra cost of the better materials with what you will save in lower premiums.

As an aside, I went through this exact situation around 2005 and so did my neighbor. I would think about an updating plan for the house as its starting to show its age. By that I mean its time to refreshed the exterior and to also update the landscaping you have what could be a spectacular home with a modern edge which is very much sought after now. If I had your home, I'd find a local architect or designer who has more knowledge than I do as to how to update your home while maintaining its integrity. It will be well worth the expense because a future buyer will decide whether to see the inside of your home in the first three seconds of looking at it - curb appeal is that IMPORTANT! And I think you have the same windows I had which were common in the 1980's the are metal clad on the exterior. Well don't worry, you can buy paint that will adhere to them. I painted mine in 2005 and only the windows on the front of my home (north) are in need of re painting. So don't let anyone talk you into buying all new windows unless and until they need replacing because the seal is gone. That trick saved me a lot of money as I have been slowly replacing windows as needed and not because they didn't go with my new exterior. I will say the cement board siding is a god send over the cedar siding. A lot less maintenance.

HI -- I think the stone work is an asset and that is the style direction I think you should go. First decide what siding look you want and then choose the roof style to go with it. I love the rustic and modern mix of this house . I could see a natural cedar siding and even some ceder shake with a red or dark metal or slate looking roof . This house would even look great with a white siding and a colored or dark color roof . Search some house exteriors for ideas . Either a Hampton's east coast style or I could see a West coast modern flair too. Having to replace the siding you should see and take the opportunity to see if the windows need to be up-dated and or replaced . That may influence your choices too.

Here you go with landscape, remember, I am NOT on site nor do I have your planting zone. It's just a visual to explain how much a good landscape design and some better color choices can change the appearance of your home.

Your landscape is currently way way too close to the house. The first planting should be a good 3 feet away from the foundation.

With vertical siding.

The stone is neat, no need to redo the chimney. What if you just went with the lightest greige you can pull from the stone?

Here is a modern home with vertical siding and updated colors with stone not all that dissimilar to yours I think it is a good reflection on how much change could occur while embracing the fixed elements with good design choices.

Try paging through some of the contemporary shed roof photos: https://www.houzz.com/photos/contemporary/query/shed-roof

Your ideabook photos show a preference for soft natural colors with brighter off white trim accents. You could take some foamcore boards, cut one to the width of your window trim, paint it in an off white that's the lightest color in the stonework, and prop it up next to the window. Paint the others with the sample colors you are considering. Easy, cheap, quick way to see what really takes your fancy.

Photos of your roof samples next to the foundation rock would be useful.

Thanks so much for the suggestions. I will consider much. I have been looking around and gathering ideas!