That's a lot of flat roof we are looking at. I would try larger windows and dormers if the money is there. That will not only enhance the outside but imagine all the light you will bring inside. The upper windows look undersized for the home. I marvel at what a great porch design is doing to some of these early 1970s small ranch homes. How will that work here given your bottom windows?

It looks like previous owners tried to turn the raised ranch into a colonial. All the ones near me have much larger windows. I don't know what your budget is, but as arcy_gw said, if you can make your windows larger it would be an improvement. I would consult an architect for design options since done right this could be awesome, done wrong you will have just spent money for nothing. You will need to address all sides of the house if you change the windows. I hope you already have larger windows in the back since it looks like you have a lovely wooded lot.

Thank you for your responses! I love the idea of dormers and larger windows, that would absolutely be in budget. When expanding the windows my fear is there would still be quite a bit of dead space on the right side between the upper and lowers. Which is where I was thinking some sort of porch could maybe work, but maybe not given the lower windows. Our intention to create an area where we could sit/socialize, just not sure how to make that happen and also deal with the boring exterior.

I am wondering what the lower windows to the right access?

opening that up to an exterior living space would be nice. you have plenty of yard on the front of the house for an addition, or outdoor living space.

The entry already looks tacked on, but it works. A portico in front of it would look quite funny. I think your biggest problem is the greige. There isn't a strong contrast with the roof or trim. I'd go with a medium to darkish blue for the paint. The roof will read as much smaller when it's not the same color as the siding. The windows on the right are farther apart than the window on the left. I'd plant an ornamental tree --- we have a lovely red Japanese maple --- between the windows, so the dissymetry isn't noticeable. But dogwoods are lovely too. Make sure it's mature size will at least reach the bottom of the upper windows and you plant it far enough from the building to not scrape the siding when the canopy is mature. We're constantly hacking our Japanese Maple (which some former owners planted)

It all depends on whether you keep the stairs inside, or place them outside to gain some interior square footage.

This is the best remodel of a raised ranch I have ever run across.

Around here, that is called a split foyer. I agree that larger windows upstairs would be nice. There are many like the modern ones that Beverly shows in her first two photos, but I think it would be astronomically expensive to change yours into one like those. I would embrace the saltbox vibe and paint. No porch.

See!? This is why I posted, thank you all for your suggestions! I’ll nix the portico/porch idea and focus our budget on windows etc. I appreciate it!

At this point it isn't a ranch. It's a Colonial. Love the idea of a porch (even though that's not usually an element of Colonial style except in the South) but the current window placement will make that very difficult.

The spare exterior, reminiscent of the oldest New England houses, doesn't bother me. (I grew up there and love those old homes.) The gabled entry does; it doesn't seem to fit the house. If you're up for it, changing the roof to a shed form that echoes the existing front-sloped roofs would help. Here's a visual so you can see what you think.

I would develop a shade garden around the trees, so you don't have to mow around them individually. If that's a sidewalk at the bottom of the photo, and if anyone would approach the house from it, the steppingstones that cross the shade garden above could become a full, curving front walk from sidewalk to door. (This just shows ground cover under the trees; you could do more if you like gardening.) Thoughts, anyway . . .