Are you set on keeping the dirt area for your puppy or are would you consider container gardening? Does the area get a lot of sun? My first thought is there is alot of brick already between the facade of the building and that two story portion shown. But the herringbone paver layout is great. If it were my home I would probably take that Trex decking and extend it over in to the dirt area at an angle and then use pots to make my garden. Really great pots that you can move around and change by adding colorful plants when the season permits and then I would invest in really nice outdoor furniture to make the space. I see you have a small teak table and with a good powerwash it can be made to look new. Then add some outdoor chairs and hang a piece of outdoor art on the brick and that would be a great start but definitely start by just getting rid of all those odd plantings. It will be a lovely retreat. Good luck.

Pull up some of the pavers and introduce landscaping into the space to break it up into smaller outdoor 'rooms' ... some shaded, some not. Perhaps a group seating area, a BBQ area, fire pit, swing under a pergola? That sort of thing. Give the old girl some character.

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Hi Amy, Isn't Houzz fantastic - it's easy to spend hours here looking at ideas and hearing other peoples ideas. If you've not already done it, get the high pressure hose out and give the pebblecrete a clean to get the colours to come up (give the lower stones in your retaining wall a clean up too so you can check their colours). Looking at the colour of the pebblecrete now and seeing that the area will be shaded for at least part of the day and you won't want it to feel too dark - especially in winter, I'd go for the sandstone look unless it's completely at odds with the retaining wall. Most places selling pavers will sell you or give you a single paver that you can bring home to check the colours in situ. I'm sure that it will look fantastic when it's done.