Roof, door and landscaping would be the first order of business. The roof shingles will come in the most limited colors, so after they're on you can determine what siding colors will work with them.

Before you replace your shingles with more shingles, consider whether or not you want any structural changes to enhance curb appeal -- even if it is only a cupola on the garage and/or adding a larger covered portico at the entrance and/or adding more prominent window framing ...

If you want a different look, then consider different materials -- such as log siding

https://www.loghomeshoppe.com/pine-quarter-log-siding.html

or vertical siding

https://www.kpvinylsiding.com/vinyl-siding/vertical-siding-touch-dramatic-flair/

You should probably look at both shingle colors and siding colors at the same time. Then, as has been suggested, change the shingles first. ( decoenthusiaste ) It will be easier to be certain your colors will go well with each other once you see the shingles on the roof.

From the front view, if the downstairs window placement didn't give it away, your home would look more like a salt box home than a split level -- one with a very prominent garage attached.

It isn't unattractive but it is a bit plain and, absent structural change, landscaping changes will likely have more visual impact. At the very least, you might consider trimming the shrubs (privacy) to have level tops.

I'm not a big fan of trying to turn a house into another style. In general, I think you just get a mishmash, but you could put corbels under your eaves, which would add a little detail and be a bit craftsmany.

Craftsman Exterior · More Info

A shed dormer for your garage would add some detail, but it might be expensive if it's not giving your extra light or usable space. Rather than extending the garage, I'd be tempted to bring the door or porch forward, like this.

The Danube plan front porch · More Info

You should improve your bushes, too.

I would definitely change the siding and replace the front door. Here are some colors that would work with your existing brick...

Catamaran · More Info

Farmingdale Vinyl Siding Remodel · More Info

Here are a few options.

I would remove the shrubs in front of the bottom windows and add something taller in the center. I would also limb up the tree on the right to reveal move of your house.

Eliminate the storm door and modernize the front door.

I really like the darker taupe and the cedar color at the top. With a dark roof (charcoal, not black) and the wood piece over the garage door stained to match and the modern front door, I think it would completely change the look of the house. Don't do contrasting corner blocks, make everything the same color to keep from chopping up the house. Does your siding need to be replaced or will a good paint job do the trick? If you're going to replace it, use the same wide size in a Hardi plank. You won't be doing the house any favors if you replace nice, wide siding with chintzy 5" vinyl.

Power wash the concrete step, add a tall black planter and modern coach lights.

Hope this helps!

@nkatter

I was basically thinking you'd add a porch that would be essentially flush with the main house.

Are you planning to remove the brick?

I was thinking a wood siding would look lovely at the entrance. Just to give you an idea: wood siding

I wouldn't add more to the roof (the gables you mentioned). As those renditions above show--you could change things easily just with color.

Do you want a porch?

Do you need gutters (that dark splotch on the concrete)?

You could easily get a more modern vibe with a new modern door and casement windows for example.

Does the siding need to be replaced? Can it just be painted?

I think you have a simple house which can be easily improved with curb appeal using some of the suggestions above. If you do add more garage bays, make sure your garage doors are not the focal point; otherwise, no one will ever notice your entrance.

@Anna

Yes we need gutters for sure, that would be part of the project as well. Not really sure how to incorporate a porch though without changing the roofline - you'll see the entrance has the same roofline as the garage, which can only extend out so far. But I do think a porch would add that much needed emphasis at the entrance, just not sure how to accomplish that.

The siding does definitely need to be replaced, it's original and in bad shape - we're planning to replace with LP Smartside.

While I love the idea of the modern wood siding, I'm afraid that will be a bit too modern for my tastes, that lean a little more farmhouse/craftsman - although I do love clean lines.

You should look at pictures of split-level remodels. You won’t get a farmhouse or craftsman look out of the house without making it look forced and unnatural. I too love craftsman and farmhouse styles but I have a ranch and I know and respect the limitations of the house.

Based on the above renderings kindly done by others, maybe just a color change will give you what you want.

I guess I misinterpreted “I’ll still have a 1970’s looking split-level” to indicate you wanted something more modern. My bad.

Good luck.

I think that Doug's design with a pumpkin colored door/and stormdoor would look great! I would avoid any gray or blue for your siding.

I would definitely get some more substantial trim around your doors and windows if possible & gives you more options on your paint scheme.

https://www.gardenweb.com/discussions/4556765/what-to-do-with-this-exterior

We have some similarities in house style. Here’s a thread on some changes we made. Maybe it will help give you ideas.