The slope in the picture doesn't look that steep, but it still doesn't meet your needs. A cut and fill method would save some hauling. Cut into the top slope and use that to fill in the bottom slope to raise it. This may give you two more retaining walls depending on the degree of slope you leave behind. The far slope could be left as is and planting if not to steep or threating the integrity of others property. the cut and fill method may allow a lower height retaining wall that can by a DYI. This will leave one Retaing wall by the patio and then a second one bit up from there. It seems a little awkard?

Design wise there is almost always a way to do this, it is the engineering that has to be sorted out . Your best bet would to speak to a local structural or soils engineer and they can either draw you up a set of plans with footing details and the appropriate required calculations for your building permit and or you can work in tandum with a designer and an engineer. In most locations you will require a permit to build such a structure that has the attached calculations and is wet stamped by an engineer.

what is it you like so much about the house? It looks beautiful on the outside but according to what I saw on your realtors website the inside is pretty common for houses in that price range. Did you ever think about finding a house with a beautiful interior, a yard you like and change the outside to the craftsman style you appear to like? Think about how much the potential house costs, how much you will spend altering the yard (while taking care of a small child and newborn) and then what is the return on the house if you decide to sell. The market is slowing down quite a bit and that has to be taken into consideration. While it is true houses are meant to live in they are also investments. I do not know anything about the area you are looking in but read up on functional obsolesence. If there is nothing in the area to compare it to there is no value in it. If you over develop your house it will only price so high meaning you spend $$$$ on a house put $$ inside and $$$ outside, you might only be able to get a very small percentage of that back on a resale (if you are lucky). Youe could lose quite a bit unless of course the market goes back up which I do not see happening. Think beyond the emotion on this one. Good luck in whatever you decide to do. It can be a heart wrenching thing to fall in love with a house and then have to deal with the big BUT. It happens to me all the time. I found the perfect outfit but it does not fit (but I can always go on a diet but the reality is that a year later it is still hanging in the closet with tags on it and now going to Goodwill), found the perfect TV but it does not look right in the room I wanted it for (but I can always put it in a different room and then i still have to buy a tv), found the perfect car but hate the way the seats feel (but I can always replace the seats but I will be uncomfortable for now)...no matter how much I love it the "buts" come into play. With patience you will find what you want with a smaller sacrifice. You probably did not get the answer you wanted here but you asked for advise and I assume you wanted honest opinions. I hope we made you think of a few things before making such a large commitment. You are talking about a half million investment so invest wisely!! I am done preaching cause I do want to beat a dead horse. Let us know what you decide and keep us posted. If you decide to do it anyway (and judging by your responses I think you will) start another topic to let us in on your project so we can all know what all is involved and how much it costs. Regards Ms Jay

The patio will need a slope but in most cases the retaining wall stays the same height. I picture of your yard would be helpful. As you can see in the picture below it always looks better when the top of the retaining wall is level and let what ever is on top or bottom slope.