You have done a beautiful job of tucking plants into the crevices of your retaining walls. Your house trim color is perfect -- just slightly lighter in hue than the retaining wall blocks. First I would paint the big, flat gray wall slightly lighter than the blocks and slightly darker than the house trim. The concrete walk and stairs I would stain a mottled blend of the blocks and the house trim colors. Next would be to paint the railing black or the house body color. Now, think of the following as creating a light, airy trellise structure from the walk-level face of the (currently gray) wall to about 7' above the top of the wall (using 6x6" posts attached to the wall) with a corresponding line of posts sunk into the terrace level 2' in from the outside edge of the wall-attached posts. The inside posts would be about 6-8" higher than the outside posts. Put 4x4" wood to attach the outside line of posts to each other and do the same with the inside line of posts. Run wood pieces at the top of the two lines of posts from the inside line to the outside line at about a 45 degree angle. They would be cantilevered up at the terrace level. Across the top of the angled pieces create your top trellise boards which run parallel to the two lines of posts. OK. There you have your basic structure. You might want to extend the structure around to follow the street side of the terrace. You could then follow the suggestion of reom10 above about creating a bench-planter on the terrace side. Your spacing of the boards parallel to the gray wall and attached to the outside posts would determine how private you wanted your terrace to be. You might want to soften the terrace "floor" by using something irregular like flagstone with groundcover plantings between the stones. From the latticework on top of your structure you could hang seasonal flower baskets. Plant vines to go up the trellis and spill down the wall. How about planting a row of tall, narrow shrubs along the neighbor's fence above your terrace to help add to your privacy and make your yard feel less 'structured'? Or, how about patio table/s with umbrellas to block your neighbor's view? Anyway, you have a fun project ahead of you.

To answer your question I would paint the body of the house blue, all trim white, and then the "fringe" which I think ties into your porch decking, I would paint it the gray. It is a good "grounding" color for your home. Sherwin Williams has a cool web tool. Take a pic of your house and load it onto their site. You can "color" away on your house. When I painted my house for the first time, I did not want the garage door to stick out, wanted it to blend into the house. Everyone said it would look weird, needed to be painted the same as the trim. Used the Sherwin Williams site and realized want I visioned looked good. I have neighbors of dubious design skills! Ha! Ha!

Excuse my duh-ness but i'm having difficulty trying to follow whats going on here. Are these two photos an exact replica of your house and pool ? If not a hasty sketch with dimensions could help a lot. By kitchen wall do you mean the wall behind the bar ? And where is the pool wall ? Are you considering the covered area as being "inside" ? Sorry for all those questions lol Sometimes when you have a design problem you need to turn it inside out or on it's head. If you can't beat it maybe embrace it by making a feature of it : i.e. contrast by having the lightest colored pool surround and a great blue or tile inside and under the overhang, something that will echo the water color ? If you have a great covered area as in photo you'll most likely be spending a lot of time there and it could be soothing to be able to sometimes retire into a darker inside. In my book, 10M isn't small and also contrasting two floor colors doesn't necessarily make a space seem smaller and confined and may in fact even open it up. Could it be that you've thought yourself into a box here ? Sometimes one needs to give it all a good shake up and see how it resettles.

With any post war house built in the 50's the connection from in to out is non existent. Depending on where living rooms are located i would take some of the fantastic windows out and replace them with French doors, or bi folding doors and connect the house to the site. The colour scheme from Karen is perfect to lift the kerb appeal and give it a modern twist. With land costing more than houses these days and the fact that you seem to have quite a big block, after looking at paint colours, opening up the living dining kitchen areas to the outside with a roofed area. Even combining a flat roofed carport which will widen the house to the street making it seem a bigger house, can carry the new look with say an enclosed section for garden equipment, to the opposite side to the house, and if you are lucky enough to have that near the living area it can be used as both car cover and outdoor living. I always think a good landscape architect is worth their weight in gold, to give you a landscape plan, to suit the soil type, your skills level and your preference in planting. Divide up the exterior space to provide outdoor rooms under a tree, paths that lead to some special spot for kids, maybe even a veggie patch with a chock run, and make sure that you use the entire yard, front and back by enclosing part of the front yard in fencing which suits the style of the house, while providing some planting to the street. If allowed a gate structure to blend in with the house, a dedicated pathway with planting each side to the front door, fantastic fencing and consider natural materials like a hand laid stone fence with timber or powder-coated aluminium inserts, to give this house an entry, not sure where the front door is now, so that is not a good look. Gardens always enhance a house, they are never a wasted effort, and if you are not gardeners, make sure the landscape architect knows that and he will be able to select low maintenance plants. All the paint in the world will not give the desired effort that the garden will do to that paint work.