In my opinion what dates this house is the overly large, tall portico. Having said that I would not go black on windows and doors. I would pick the darkest color from the stone. As for black roof I think it is much too stark. If you want to go darker go charcoal

What Ruth said. I'd spend my money fixing that tall portico with oversize roof.

Black everything is such a trendy thing, I would soften the black to a less stark contrast.

Where I live in the Mid Atlantic, pollen is a bitch on black trim.

I couldn't find an example with white windows... you didn't say you were changing out the windows, right? a Black roof is very severe, a dark gray with some variations would be more pleasing and less bird poop stains showing.

this pix may help show your husband the concept.

Honestly this seems like a bad idea. You are going after trendy black. I don’t think it’ll suit your lovely home.

Is this a split-level?

What is behind the space above the door? If it is just a high foyer? Could you add a window?

It is a raised ranch with a high ceiling/foyer

In fact, our house had one of those tall ceilings in the foyer and a structure similar to yours, except we also had one of those dreaded round top windows circa 1990s. We removed it and used that open space on the second floor to create a home office. It looks and functions WAY better than before.

I think that often thoughtful/professional landscaping gives the best ROI on updating a home

Your brick looks like it leans brown, not gray. I agree with the other commenters that black windows aren't a good fit here, nor would a black roof be a good idea. Depending on which manufacturer you use for your roofing, they might have a color named Weathered Wood which would be a better fit. You can't get to the "modern" look you want by applying trends. The massing of your house is contrary to true modern. The front door you're showing isn't a good fit either. The house would end up looking worse if you do any of the things you're considering. You could paint your trim and garage doors a darker color, but don't go too dark or else the overall look will be oppressive. If you love the interior and your neighborhood, then try to learn to love the exterior. It is what it is - if you really want modern you'll have to look at moving.

A black roof will make your house awkwardly top heavy, absorb a ton of heat, and increase your cooling costs in the summer.

Your current trim color on the portico goes well with the brick and roof. I'd consider painting your garage doors, window trim, and front door and windows that color.

You could do your front door and garage doors in wood instead, but I think finding a color of wood that looks good with your bricks, you'll end up with something in a greyish wood tone and might as well just paint instead.

Get a more modern, larger, and attention grabbing light to hang in the portico. It will take your attention way from the dated portico itself and towards a more modern element.

I'd also create a more contemporary planting scheme to the left of your door.

I would rather go with dark color from your brick than black.

Roof looks nice to me.

It seems the newer homes around my area are adding stone to the brick in accented areas. What if you added a coordinating lighter stone to the portico?

If you're going to tackle the roof, I'd reduce the height of the entrance canopy.

Your home has 'Carriage House' details. IT WILL NEVER BE MODERN WITHOUT EXTENSIVE REVISIONS WHICH WILL NOT BE WORTH THE MONEY.

I would not consider anything darker than bronze for the windows

Get rid of the light color on any trim and the garage doors.

Again I would consider reducing the height of the entry canopy.

The existing door is a better fit with the style of your home, unless you want to start pushing the home more traditional.

It would be easier and more appealing to push the home to the traditional side than the contemporary side.