As much as I can appreciate your vision, it seems the siding, chimney and porch need some work first. I love the stone wall, and would just rebuild it using what you have. If you are itching to build the wood retaining wall, maybe you can use the stones to make a flower bed to the left of the porch. Also, there must be a better way to hide all the cables hanging off the house.

I suggest huge pots of the classic red geraniums along the side of your house. The red and green will look fabulous and definitely be great curb appeal. Your front yard looks pretty mangy but the only thing you can do there for a relatively small amount is cover it in large plats of grass but be sure and follow the directions on taking care of it exactly or you'll have a yard full of dead grass very shortly. Simple. Easy. And not horribly expensive.

I think you've answered your own question. fix the crumbling flower bed/wall, make a nice pathway and put in some new plants. But the house still needs painting, or cleaning off that giant dirty spot. maybe a good washing? other than that, until you get some funds to make repairs, it's still going to look like does.

There is a big crack in your chimney. That looks like a hazard. You should have that check first - soon.

Cute house.

There is no reason to have a raised bed. Unless you can have that wall re-laid well and professionally, get rid of it. The same goes for any retaining wall. It's a flat lot; there's nothing to retain. It doesn't give you any appreciable height and it looks ragged and run-down. Plants will give their own height.

Paint all the foundation a medium dark-ish natural color and it will disappear behind the plants.

Very cute house!

I don't think you need to replace the retaining wall. Seems like an unnecessary expense to do so.

IIRC, you need >6" between the bottom of your siding and ground cover. I just landscaped around the front of our house and chose 10" between siding and ground, adding a couple inches of river rock, creating a "maintenance strip" around the house.

If mud is getting tracked in the house because of that dirt path, I wonder if you could repurpose the wall stones as stepping stones?

I'm all for curb appeal. However, as others have mentioned, you have some repair issues that trump curb appeal for the moment.

You have a cute home with character. I hope you had a very detailed inspection before your purchase. If so, start with the repairs in the report. Some inspectors are better than others so you might even have repairs that need to be done that aren't in the report. If it has been a while since your purchase, then you will probably have a good idea of where to get started.

I agree that landscaping is the best way to improve the look and this includes your retaining wall and walkway. Before you go down that road, take the time to fix the big items: chimney, retaining wall (keep or not), walkway, etc. Good luck. It looks like you have a real gem there :)

The crumbling wall is surely a not-well-thought-out, prior homeowner add-on. You don't need it and it would be better to dispense with it. Maybe you can use the stone for a better project in the back yard. Foundation planting has to have space if it is to be any good. Therefore, move the walk away from the house. Have a nice landing at the base of the steps. Widen the steps and the walk. Those are some simple things you can do that will make a big difference.

Thank you guys all for the suggestions!! We had the chimney looked at and while it is maybe not beautiful, it is structurally sound.

I think we will widen the steps as suggested by groveraxel and Yardvaark, although this is one of the more expensive suggestions and we may need to wait to do this. I also think the idea of moving the walkway a little further from the house makes sense--it eliminates the need for retaining wall, gives the dirt that's currently in the raised bed a place to go, and gives room for planting. How much room is best?

Finally, we will paint the house (and paint the chimney to match) as soon as we can. That lovely stain is actually uneven fading, I believe.

As you rethink your landscaping, consider what changes you'd make to the house itself IF and when your budget permits so your landscaping (because of what you spent on it making you reluctant to change it) might block some change you may want to make later.

If you're not planning to add to the front of your home, choose shurbs that thrive in your area and keep their leaves year round. (In Zone 7, I'd suggest aucuba.)

If you're even considering changing that front "half gable" into a wider full gable in order to have your door in the front exterior wall rather than opening toward the side of the home and/or if you're even considering building a front porch, make your new sidewalk from your front steps lead away from the house far enough before turning toward your driveway to do that.

Planter box with trellis could be placed to hide any discoloration of your siding.

I like the green siding with the red roof, but if you're thinking of eventually changing the color, keep the future color in mind in choosing colors of plants! I think painting the white trim a darker green would de-emphasize the irregular shapes and positions of the windows. Paint the stair railing the same darker color and it too will fade.The chimney, on the other hand, is a feature I'd keep as prominent though perhaps a brick (i.e. faded) red, not white. Hope you'll keep us apprised of your progress as this is a house with oodles of potential charm.

Have you thought about painting your front door a soft yellow? I think it works well with your siding color and your roof color.

Buford Road · More Info

Another inexpensive tip is to have large, easy to read address numbers where you have them now, but something with a little flair. Maybe you can design and craft something along these lines:

Metal Wall Planter and Address Plaque, Rust, With Numbers · More Info

Placing the walk at least 6' from the house wall will give you the minimum necessary for a decent foundation planting. If a walk route works out to be farther away, that's OK, too.