Leave the brick alone; it's the best finish on the house. It has visual texture and depth that paint will destroy.

The thing that bothers me is the front door. It's not in keeping with the style of the house; it needs to be more modern. Paint the storm doors to match it, otherwise they visually shrink the door from a distance.

I'd paint the garage door to blend in with the brick (or, better yet, replace it with a sleeker, modern one that blends).

I'd paint (or replace) the windows to blend with the garage; same with the gutters (and especially the downspout in the middle).

And I'd re-do the shrubs--not so solid.

I like your brick. Modern doors and a wood or wood look garage door are great suggestions. I think modernizing the landscaping would help things a bit as well.

Sage green popped into my mind! Garage doors cause visual pain

No matter what else is going on , so I think tatts has good ideas there.

I'd focus on redoing the front planting beds.

Leave brick and windows as-is.

If re-roofing, I would invest in a more architectural shingle. The current roof looks flat and cheap.

I like the brick. I also dont mind your roof. I think the color works well with your house. Some new landscaping could improve your curb appeal, and add a bit of color, either in plantings, or some large pots with colored plants. I agree with the others, about your garage door. Either paint it to match in with the brick, or replace it in a newer more updated style. Looks like a very nice house. I would never paint that brick.

Brown brick is NOT "dated" - not sure where you got that idea.

What does often look kinda blah is a red or brown toned brick in combination with white. Consider swapping out the white trim etc for some jazzier gray or earth tone (would help to see a closeup of the brick) and yeah the wood garage door would be a total game changer for your house, especially if you could get a wood front entry door to match.

Here’s a close up of the brick:

Matthewklara: Now that I see it up close I feel even more strongly that you should not paint it. It's because of the way your bricks are laid. That mortar joint is referred to as a "nail-struck" joint. The wall is laid and as they go, the masons rake out the mortar to an even depth with a tool with nails or other teeth in it, then smooth it out.

That is a rotten joint for painting. You're not going to get a subtle brick pattern showing through. What you'll get is a grid defined by the sharp shadows of the overhanging bricks--light brick fronts, dark, shadowy grid of joints.

And it shows dirt and dust like crazy.

I don’t think it looks dated. It’s a classic at this point. Would not paint. Ditching the brown roof would be an improvement IMO. Helpful Maria Killarney blog post about why brown rooves often don’t work: https://www.mariakillam.com/roofcolours/

Maria Killam, not Killarney. Darn autocorrect

I would like a sheer whitewash or pale gray wash on the brick, keeping some brick color visible. Gray roof. Lapis blue or mid-tone blue/gray trim. Red door.

Your roof is fine. I'd do a bigger front porch, a new garage door, get rid of those hedges and simplify your landscape.

Paint your downspouts to match your brick.

I like Grover’s rendition but I think a darker roof and painting that small gable deeper color would be good. Also change the front door.

I wish I would have gone black windows in my 56 MCM ranch and I think they would look great here.Do not paint the brick it is IMO the fastest way to devalue your house no matter Joanna Gaines says. A charcoal roof and the some really cool MCM landscaping and a MCM front door

Here's a dark gray roof. I don't know what's going on with your door, but it looks like you could use a new one, so I gave you one in acid green.

And here's a dark roof and dark window and door trim. Because the brick is fairly dark and the front of the house shaded, I like the contrast of the white trim better:

Blue contemporary door could be nice. I darkened the brown roof a bit & fluffed up the landscaping.

[I disagree with Maria Killiam about brown roofs, btw. They look great here in the woods & rocky outcroppings of the U.S. Northeast, blending in better with nature than a heavy black, tarry asphalt roof.]

Here's the darker roof, not the first picture.

Here’s an updated pic of the house in the summer. Really appreciate all the ideas so far!

It's a very nice house!. It's great to see it in the summer also.

Another vote to not paint the bricks. But changing the roof color could make a nice change.

Agree with above - the giant yew blobs are the only "dated" features. Grover's version with the darker window trim gets my vote.