Garage has black metal roof, dark gray siding and white trim.

What I'd do first is spend money on landscaping around the house: shrubs, trees, flowering bushes. Evergreens would be a good choice in a cold climate.

You have a very nice home!

Agree with kudzu9 - landscaping is going to give you the most impact.

I can't see how large your current walkway is right now, but it looks like it is too tight to the house. Is there a way you could widen it to at least 48 inches wide and have a more pronouced curve?

Paint the front door an accent color that is lighter so the front door shows up. Right now it is so recessed and dark that it has the black hole effect. A brighter, lighter color will make the front door come out of the shadows and make your front so welcoming.

No shutters. Your windows aren't the right shape or size for shutters.

This very brief article will show you why your windows won't work with shutters: https://www.lifeofanarchitect.com/residential-architecture-101-shutters/

You have a beautiful house. I, myself, would not make changes to it in order to coordinate with a pole barn. Does the house need a new roof? If not, I personally would not replace it at this time. I agree with the other respondents to focus on landscaping.

Thanks everyone for the input!

Landscaping intimidates me, so I hadn’t addressed that yet.

Good to know about shutters. I had no idea.

There is actually concrete all the way from the front door to the garage that juts out on the right. It is all cracked and not in great condition. The plan is to get rid of it and just have a decent sized sidewalk from the front door around the garage. Probably put some sort of decorative gravel in the remainder of the space

We will need a new roof in the next year or two. My husband is leaning towards metal, but I’m not sure it goes with the style of the house.

Landscaping for sure. That will make a vast improvement. I'm with your husband. If you can do a metal roof that would be awesome. I live in a house that had a metal roof installed in the 1940's and it was still in good shape when I left in 2000. A standing seam metal roof would be great. You might consider a light colored roof - perhaps galvalume. Would suggest you remove the elongated hexagonal vent in the front gable and replace it with a less dated shape. If you decide to paint the brick replacing the vent should be no problem as you can find a brick that's similar texture and paint it along with the rest. The column at the entry stoop seems undersized. Would suggest replacing with one that has more beef to it and would give it a brick base to match the rest of the house. It's quite a nice home btw. Good luck!

I would do a metal roof for sure we are doing one very soon. I agree landscaping is going to be the biggest bang for your buck. If it was mine I would do windows with no grids, definately no shutters , a new door and then see if you need paint for the house . I do not think the pole barn and house need to match but a darker color on the white parts of the house might work. I think the entry is very small for the house you might want to see if there would be a way to widen that.

Stall on the roof while you do some research IMO. If your home photo is current (as in this week), since you don't have leaves on the trees yet and your lawn is brown, you evidently live in a northern area with snow? In those conditions, standing seam seems to be the way to go....

HOWEVER.... and this is why I say to research first. See how your house is in the blazing sun? Research solar. My roof is purpose-built for solar, neither standing seam nor shingle. I've been getting at least some solar power all winter (except one month), yep, even though we get a lotta snow here.

If your state has an agency for energy efficiency—as mine does—get their advice and see if they have grants for solar or incentives dependent on income.

Tip: If you're researching solar, also find out if your state has net-metering. That way, you can generate solar in summer to pay the bills in winter. Cost out EVERYTHING for your overall savings, and not just the expense of the solar panels. Cost out utility savings per month, projected increase in value of home, tax reduction, if the roof costs less than a standing seam or shingle because the materials/techniques are different.... Arrive at your long-term savings, not just your short-term expense.

Make sure you do a LOT of research on metal roofs. My wife is an insurance claims adjuster and they have many claims where the screws holding the roof down leak. With the expansion and contraction of the metal roofing material due to changes in the weather they screws loosen and allow water to leak in. Plus your home style is not usually seen with metal roofs.

If you did want to change the siding I would probably go with a warmer gray (taupe) that works better with your brick color.

I'll repeat what others said, landscaping, landscaping, landscaping. That's going to have a huge impact.

If you're interested in seeing some virtual makeovers of your home check out my website, Creative Visual Concepts. I can show you how different treatments and things such as landscaping would look.