I think your house is lovely. I’d start with garden beds in front of the brick foundation. And, of course, put the bicycles and dumpster somewhere out of view. Can’t really see the walkway to the front entry, but perhaps it could be made more prominent and landscaped.

I’m sure you’ll other suggestions here, but it don’t see traditional and classic as ”dated.”

I agree this is SUCH a cute home! There is so much you can do!
I’d start with landscaping plan.
I would possibly remove the small tree, just because it blocks the view to the porch.
You can put it back into another spot maybe.
Then go all in with the front brick planters and walkway.
I’m picturing some pretty vine style plants in the mix :)

New outdoor lighting.

Now the next idea I have will take it to the next level. But can be pricey. And has some logistics to it.

If you can, and the interior allows, I’d add two sets of French doors leading to the front porch.
It’ll create such a lovely moment.

And then maybe paint the door a pretty blue.
Porch ceiling blue also?

I think what you are missing our front windows on either side of your front door. I don’t believe I’ve ever seen a house with no windows facing the front. That would help tremendously. The columns on the front of the house need to be a little bulkier. That’s easily solved by just wrapping the columns with 1x6 on each side and Finishing the bottom with a base and may be a detail at the top. A front walk would be lovely coming down from the front door and may be turning and finishing at the driveway depending on where you’re parking situation is. You’ve got a great start of a beautiful house. Good luck

I like the suggestions above and would also suggest a porch railing. It will visually fill the vertical space on the first story.

Some walking way to the driveway with plants on sides. Beef up posts.

you may have some hidden windows under the siding (inside under the wallboard) have you looked? I'd take a chance and open it up to see.

A color such as this BM Wythe Blue is so pretty with the brick and is softer looking than the black on your front door and shutters. Definitely add the windows on the first level, hope they are hidden but money well spent as they will really enhance your curb appeal. A walkway to the front door is another good investment as well. Plants in your boxes would be good too, a mix of upright annuals and hanging vines would soften the lines of the brick planters. Changing out the white cushions on your chairs to a color would make them more visible. It's a cute house, you are lucky it's not a complete do over!

How far do you want to go? If it were my house I would want to do away with the peak in middle of roof. Most definitely you need windows on the bottom. I would also do away with the wood structure in front of porch. I'm wondering what's behind it. Do away with the small tree on right and make large flower beds in front.

LOL, I see two eyes, a nose and a mouth! Adding first floor windows would definitely help with my distorted view.

If cost is prohibitive and windows not an option, I would get a trellis for the front porch and plant some clematis or other vining plant. Looks like the right side might be sunniest. Agree with other recommendations. A nice winding brick pathway - herringbone pattern to driveway might be nice. Love the door color recommendation as well as redoing retaining wall beds to make more symmetrical. Mums and pumpkins would look nice this time of year. Happy home decorating!