There is enouph room to put a path on the side of the house. It looks like it will go to the back patio. So the material should match or at least coordinate with the patio. It should be at least 3 feet wide. You may not be able to make it much wider than that since there is the grading issue and you HAVE to take some dirt out and flatten the area for the path. The path goes next to the flower bed which is next to the house. Of course you can take off the flower bed totally and use it for the path. Depending on how deep your retaing wall goes, you may be able to slope what will be left on the other side of the path. Planting can help to hold the slope. If that does not work you can have a second retaining wall to be build in front of the other. Another alternative will be using large stones/boulders to have a raised bed. Again you can plant this area. Azeleas are great for shade as well as many other evergreens. I actually used large boulders instead of retaining wall and worked beautifully. Of course, in the front you can do whatever you want to. I would continue by curving the path and enlarging the front beds.

The part I would worry the most is where it stops at the sidewalk. If there was some way of putting another course of the stonework across there to stop dirt/debris moving out of the garden onto public space I'd feel happier (if it were mine.) I don't know if you get snow in winter, or interesting frosts that affect your steps. What impact would having a raised bed there have on your ability to clear snow? If the mulch stays in one place (apart from the birds helping it to move) then you shouldn't have a lot of runoff or downhilll movement of soil. You don't say what you plan to plant there. In my own zone I could think of natives that would tolerate that depth of soil, despite the rubble below. And heaps of weeds, too. Not to mention shrubs and herbs. I'm just thinking that stooping over from the steps to garden could be quite demanding. I like your wood constructions. And I like that blockwork you have out front even better as a match for your house. As well as this forum - you could offer the idea on some of the other forums that get more traffic than this one. PS Love your boulders! They look sort of glacial. Very pretty!

The retaining walls are a bear of a project. That's something I would hire out if possible. I would first get copies of local building laws (state, county and municipal) for the retaining walls since you wouldn't want a telephone call from a neighbor to undo your work and since the saftety part of such laws is for your benefit. I know there are formulas for designing the walls but can't say offhand what they are. From the photos it looks like the slopes are a bit steep so a series of terraced walls would probably look and work better. If you do a series of terraced walls then you can plant up the terraces with plants that are not too heavy such as flowers or small shrubs. I would be hesitant to plant trees in terraces. From the photos it looks like the area gets a good amount of sun exposure so sun loving flowers might work. Some sort of interlocking block product might be good for the retaining walls since you can go at your own pace (one block at a time over several days if necessary) after the prep-work is done and since such walls are less likely to fail from heaving or from excess water buildup. Wood ties are probably easier and less expensive but will rot eventually. I'm guessing that the path to the pool will be paved or stone or whatever since you don't want to track mud into the pool or the house. A grated-covered drain near where the path meets the pool patio might be good so that water flowing off of the path during rains will not make a mud pit right near the pool patio. The path should be graded to slope down away from the house of course. I would also suggest observing the area during and after a good sized rain to see what drainage issues in the area might need to be addressed. Attached is a link to erosion control magazine which you can read and search for free online to get ideas and to find out suppliers of products. Here is a link that might be useful: erosion control magazine

I wouldn't call this a real Tudor, more a mish-mosh with some Tudor trim. That is why it doesn't look "right" to you (or me). Half-hearted gables, the door is wrong and lacks importance, it altogther seems not graceful. If you don't want to pull off the faux half-timbers, you could paint them out -- make them fade into the overall siding. You need to decide which direction you want to go -- I think there might be things you could do to "fix" the Tudor look to an extent -- changing the dark paint in the gables would be a start, maybe adding another texure (stone or brick) around the door area. As many have mentioned above, the right color scheme can make a huge difference. My inclination would to go in a direction that might suit the overall shape of the house a bit better though. Your roof's shade of brown is not a bad one and can work with several greens, blues, reds and, of course, neutrals including a few grays. You are lucky that you can paint which gives you infinite color choices. If you don't want the color to pop too much because you are close to the street, choose a muted tone. There are lots of gray- blues, blue-grays, green-grays that would lighten up the house but not be too strong.