Here are more pics of the front building (the close ups) and the back house too. You basically can't see much of the front house from the street... mostly the roof & some big overgrown bushes :)

Paint them 2 modern colors- solid, no trim, and in a sating or eggshell finish. Imagine the front house in dark, inky blue, and the back house in a bright barn red, or lime green.
I'd paint the concrete a darker red, and eliminate the parts of the crazy walkways that you don't need.

It would be fun to landscape that yard, but, for now, consult your nursery, and a lot of fast growing succulents would look cool.

thanks @keenplanner! Those are fun ideas :D

Simplify.
Where does all that rain go that washing down the hillside above you?
I suggest you install a porous pavement all across the front yard to stem the flow and protect your property from future damage.

Take up all the pavement in the front yard, excavate the soil from those areas not in planting, even across the open area to the right in the photo. Put down a heavy drainage layer of gravel, with an overflow to the wooded hillside to the right.
Compact the gravel, add a layer of stone dust, compact that and add your porous pavement of brick and flagstone or whatever you desire.
The area to the right becomes an outdoor room, a front terrace bordered by the green hillside, and offering a pleasant picture from inside the home.

At the house in the rear, draw a huge circle on the pavement from one corner of the house, way out toward the front house, and then back to the other corner of the house.
Lay on that circle a broad band of brick pavers that are very thin. They may call them thinset brick pavers. Wallah, another front terrace, arrival court, welcoming area for containers of flowers, a few chairs and a pot of coffee.

I don't know that I'd jump right into planting a bunch of different things yet. Gardens are a work in progress. You'll need to decide what sort of garden speaks to you and plan out the steps to get the look you are wanting without too many different plants or colors. People often go to the plant store and get a few of this and a few of that. It rarely looks good. To me, garden and house wise I'd either trim up the bushes or remove the ones that are clearly too huge for the area (right side of picture) if they can't be trimmed. I personally hate square shrubs and would rather plant ones that will not grow bigger than I want in the end. PS: I think your house is cute.

Whitewash all the pink brick everywhere and paint the two houses in two different colors you love that work to play off each other. Trim up the in ground plants.

Thanks for all the ideas so far! Just wanted to mention that we have a stream behind our house that has done an amazing job taking the rains so far. I'm happy to report that whe we've had flooding in our neighborhood, the water has always kept running out the back as long as our fence is clear of clutter. We've lived here 10 years but have done mostly inside renovations :). I have this sketch I made on my iPad of some color ideas and possible decking on the right side coming out of a slider that we'll update. All the brown markings are wood like a cedar (box planters; an awning on the back house) and I like those concrete rectangles for the front. All of this is a work in progress of course. :)

@Cascio Assoc-- thank you for your excellent advice!! I'm thinking a landscape architect might be an important investment to make sure we get this right.

Oh! Lastly... I should've mentioned we're in major drought territory (SF Bay Area)- thus all the dead grass! :)

firstly id suggest artificial also known as turf secondly id suggest a nice stone pathway and bright flowers that don't require as much water and if u put down a stone walkway go for a nice reddish orange so basically a burnt orange and if you could try getting rid of a few trees that will distract from it and if its still within your price range id suggest to re paint your house a nice color maybe resembling a traditional Spanish house

I really like eco enthusiasts picture number 1. I can see your house in there.

Please research using synthetic lawn before using as suggested earlier. Not an ecological alternative. there are numerous reasons i say this - creates a "heat Island", no carbon exchange, may have more runoff when it does rain and it is expensive and not interesting to look at. Better idea is decoenthusiaste's.

I would actually paint both the main house and the back house in "white", but with the door a nice bold dark color to stand out (like charcoal gray or dark blue). In the main house the pavers leading to the house look very nice. I would plant something that starts from the beginning of the walkway straight leading to the front and following the curvature of the walkway on both sides of the walkway thus defining the main entrance to the house.

It screams paint to me(two tones dark and lighter)...same on both houses(so they look like one place instead of two....(maybe even a connecting walkway, I would replace the clutter flower pots, with a couple tall grass like plants/or raised garden areas. Also trim the trees a bit. If those are asbestos shingles, better ck. codes on those before removing or painting. Solar panels might be a good investment, looks like you have the roof for it and with things the way they are... may come in handy, best wishes and remember what ever you do, enjoy it. :)

Open up the view of the house & make it more inviting by seriously thinning the tree to the left of the front door and removing the shrub/structure to the right of the beginning of the walkway. Live with the look for a little while & see what occurs to you. Get some professional help by either consulting a landscape designer or just taking pictures to a good nursery & asking for ideas. You might be surprised what help they can be. I am having good results now in the Bay area with various grasses, river rock and ground cover.

I would paint both houses alike & unify the look with plantings, walkway design, etc. . A distinctive color for the front doors. Also trim and maybe shutters. Not easy right now trying to landscape in the Bay area. You have lots of potential in this property. Good luck. I would love to see the progress as you move along.

I really like all the ideas presented. Sandra and I are thinking along the same lines as my first thought is to deal with the existing trees and shrubs first. Nice property.

I think I would have the retaining wall repaired before it fails. Maybe it is the angle of the photo. It looks like it is tilted. Make sure there is a drainage system behind the wall.

I would experiment with tubs and tubs of bright flowers to see where you might want to put permanent beds. I look a the picture and it seems no one lives there. All the major changes are fine but little personal touches make a home alive. Everything is green or brown now. Color will inspire you to make the next change. Keeping the drought in mind, there will be less water lost.

Remove all the trees that block the front of your home. Add new paver or brick pathway and driveway with path lights. Fresh new lawn a must. Flower border at around the house.
I envision main house color in a taupe with crisp white accents, maybe black or red front door. New garage door in carriage style look.

I'm surprised that no one has commented on your windows. Given that this is a major expense, your budget may not allow for this. However, from the photos it seems that there is an inconsistency in the windows not only in style but in their positions, which creates an imbalance. I would suggest having an architect, designer or window company provide you with some plans for window replacement. Some of them might even need to be placed differently....changes of level or size. All of this is costly but perhaps necessary to get the look that unifies and upgrades probably the biggest investment you have ever made.....your home. Also, your home deserves a more important entrance door. Once you have it as a focus it might also determine how you re-design the approach to it. Are the steps and walkway both necessary? The property at this point in time seems to appear in many ways from the curb to be cut up: with two houses, many disparate window openings, a too-small front door and a lot of disconnected plantings and various approaches (driveway, walkway, steps). My feeling is that all of the other cosmetic changes you make re painting, roofing and landscaping will still leave you with two houses that have a major issue unresolved unless you first address the windows.

i would start by freeing up your windows by trimming or removing branches or even the tree that is blocking them

I agree with Sandra re thinning the trees and living with it a while - if you cut them down it is too late to have regrets! Also, perhaps your climate means a little shade is welcome? We planted a lot of wild grasses, flaxes, toetoe (NZ native similar to pampas grass) to get a garden that looks natural and a little wild, but is easy to keep tidy. We have a view over fields and distant mountains, and didn't want anything to detract from that -do you have a view - aka borrowed scenery? Re your front walkway, embedded railway sleepers surrounded with riverstones look wonderful if rustic is your thing - also good in a dry climate, and look stunning surrounded with drifts of succulents and low growing hot climate color - mesymbranthemum, arctotis, daisies. I could see your house painted black or dark charcoal, with a statement color on the door that says "welcome" ie, bright yellow or turquoise. White window trim always looks sharp against black siding. - also, I love the mismatched windows - matchy matchy is boring! They suit the house, wow, have fun with it.

It's always presumptuous to assume that someone would have the same taste as my own... so I offer this with humility! I would also note that I would remove or consolidate the many potted plants infront of the buildings. It can looked cluttered. One larger planter or three planters staggered in size in a grouping can look more "intentional". You have a beautiful property! It's just waiting for some love. I forgot to note in the sketch that I'd remove the smaller tree in the foreground. When doing planting, choose just a few types of plants to use throughout to give a cohesive look. Have fun!

Your home could use some softness and de-cluttering of the general appearance, in my humble opinion.

I would paint the two homes different colors, but keep them natural and compatible with each other (like the front one in medium taupe and the rear home in dark taupe), so the eye doesn't see too much chaos and the homes are noticed for their design, not their contrasting colors. Use different trim colors on each home...the rear home could use some deep brown and maybe a teal or rust and the front home could use a lighter taupe and black, for example.

I would rid of the excess concrete. If you cannot afford to do that, consider acid etching the red color and then stain it to a color that blends nicely with your home.

The front home could use some softness and some height at the outer corners with some color and medium height to lead the eye to the front door. Having some lighter paint and flower pots at the front door would also help pull the eye and guests there.

I'm not so sure the planter boxes in the front of the home would give the home any soften balance to the boxiness of it, you could use some nice landscape beds and nicely planned plantings with both shrubs for a foundation shape and perennials for color and personality.

The existing small trees could be removed or they could possibly be pruned to get a shape that flatters the home more and allows you to see more of your home, while still providing some height and the trees would look nicer and grow better, too.

You have a great property and so much to consider and so many possibilities.

Remember to keep the potential for resale in mind, if you do not plan to be in the home for a long time.

I say paint both houses the same color. Go with a deep, rich color like gray or olive and go with white trim around the windows and black shutters. The landscaping needs a good trim. The tree right next to your house good possibly be saved (thus keeping some shade) with some serious thinning out of the lower branches. I like the idea of the brick pavers but it looks like they've been patched over the years. You could paint them all the same color or replace them. (I'd only keep one pathway; having two eats up a lot of yard space.) I agree, also, that using local drought-resistant plants with a rock garden is probably the best (& easiest) way to go. Good luck!

Color and landscape ideas in attached photo.

I'd keep the front home a bit lighter in color to help give it more presence and the rear home a bit darker, but in the same color family as the front home.

The rear home could handle trim in darker, lighter and accent colors.

The front home, though, needs simplicity and unification in its colors to avoid chopping up the size of the home. Focus on playing up features and especially the front door, drawing the eye there.

Notice, in the photo below, there is a softness in the front planting bed, because of the curves and depth from making it pull away from the home in strategic places and the white trim establishes a rhythm, while making the front door the focal point. The same could be accomplished with simply shaping your landscape bed in this way and the raised bed isn't a must.

The addition of color via flowers at the front door also helps.

A covered front entry way, which isn't a terribly expensive addition to the front home would also really give the home some personality and add focus and draw the eye and guests to the front door.

In this photo, the relandscaping is new, so the shrub growth is small, but note that shrubs with height are used between ones with mounding habits. Plants with mounding habits add softness, while the few with height keep the rhythm going and fill in between the larger tree on the left.

Also, note that the tree on the front left has been properly pruned to allow healthy growth and to avoid blocking most of the home.

That tree becomes height and an accent, rather than blocking the home. Although, in this photo, it is a dogwood, which is easy to prune to get this nice look. If your tree is a honeysuckle bush that has gone crazy, rather than a tree, it may not respond the same way.

Some simple things that won't cost tons are to line the walk to the main door with some colorful plants that grow without much water like lavender. Also a colorful bench between the trees in the front would add some color and maybe a birdbath surrounded by some grasses that are native. I would add some stone around the main entrance and use a darker shade of paint for the surrounding areas. Some garden flags in bright colors will also add some character. Good luck.

i like the light green with white trim. i would try to make the front house look more like the back house. i would start with cleaning up the front yard - there is just too much going on there. pick the best paving material/look that you have and try to make the others match or get rid of them. it looks like someone tried to put pavers everywhere they thought a pathway should be. you don't need them unless it's a high traffic path. grass can be walked on also. maybe you can use the paving materials in the back yard so you don't feel like you're wasting them. once you clean up the front yard and put some flowers in, the place will look so much better.

The first thing I would do is get a hard scape plan. Implement that before you plant anything. Your pathways and driveway, etc need to be harmonious and cohesive. Think of it as getting a clean, ordered canvas before you paint. Then let the canvas speak to you and tell you what it wants. Work around any drought tolerant, well established plants and trees that you love.

I think the most glaring issue is the walkwalys you have disecting the front yard area in the front house. Even your Ipad design has included these angular walkways for some reason. I would eliminate those immediately before doing anything else.
Next would be softening the hard look of so much concrete/paving. Is there any chance the back house could gain ingress/egress from some other area? Possibly you could consider that which would open up other landscape possibilities for both structures.
I can't offer suggestions on plant material except to recommend that you consult with professionals for proper selections of plant specimens suited to your native region and selected for proper sun/shade tolerance, etc.
Paint color choices are endless. I would go very dark on the first house and include some more updated uses of reclaimed wood or at least getting some stained or natural wood somehow in the landscape or home design.
The back house could use a little enhanceing so it's buffered a little from the harsh aspect of concrete paving. Trellis, pergola or some sort of partion wall to soften the front view. Colors of some complimentary color to one you select for the front. Don't do 'matchy-matcy' . go bold or go home!

I just have one simple suggestion. This regarding how you paint the two houses. I would like to suggest that whatever color you paint the one house, that you paint the trim around the windows, and the entire front door of the other house that same color. And then do it the very opposite for the other house.

So if the front house is painted mostly olive, but the front door and the trimming is painted red, then the back house will be painted mostly red--with its door and trimmings painted olive. I just think that would be stunning.

Yellow for the front house with any trim being white, the rear house should be painted white with yellow trim and some of those trees you have in front of the house shoud go they are blocking off the look of such a sweet little house and spoiling the exterior appeal

Please don't contrast the TRIM color. The fascia and window trim on this house offer ZERO interesting features. Also, get some GREEN-B-GONE! To paint the house 1967 school lunchroom green only competes with the natural landscape greenery, and is about as appealing as those school lunches. Try 2 or 3 shades of light warm putty GREY that coordinate with the roof. You can find the perfect colors in the trunks of your trees. NO nursing home white on the house!!! Don't pick out the TRIM except for the front door (something bold like black, red, very dark grey, or dark stained natural wood ). Eliminate all the junky brick-a-brac along the front of the house. Focus on the ENTRYWAY. Maybe real copper RAIN CHAINS flanking the porch with very large real terra cotta URNS. You could paint the back structure a darker coordinating medium grey. You don't have to match the house. Maybe do some dark grey/chocolate window boxes under the short front windows. Remove all shutters. I would use dark chocolate mulch (not red), and maybe a dark wood bench.

OMG thank you everyone! This is amazing; I didn't get alerted that I had so many replies and I'm thrilled to see this here. SO: Status update... To address a few things:

- windows- I agree- definitely an issue! All different; added at different times from previous owner; lots and lots of additions to the original home! I'm going for unifying the trim with a small window sill on all. I can see now, from looking at the pictures, that they do look super varied, but it's not as bad as it looks in those pics (which is good news). Also might be removing shutters from back house 1.) because I need to add an awning because that unit has hardly any summer temp control, need to block sun 2.) there are barely any other places on other front facing windows that have room for shutters.

- paint: I think I'm going with Benjamin Moore Chelsea Gray for the house(s). I'm still deciding on if the two houses should be the same or not. I still need to explore that. Trim will likely be a warm white, not as white as the vinyl windows but not too different either.

- walkways: we are going to change it to one straight from street to house (not necessarily following the driveway but a direct path from street), and we're keeping the walkway that follows between the front door and the driveway, because we often (but not always) go that path to the cars. I did the angling walkways in my iPad drawing not because I'm going for that look :D but because I was just trying to see what rectangular pavers would conceivably look like. Definitely not going for a random angled walkway look.

- retaining wall- YES! it's a total issue. We are going to get ahold of the original company who installed because OMG what's up with that! We paid so much $$$ for that 8 years ago...

- existing plants/trees & new plantings: definitely changing up the plants. I love dryscapes with grasses and lavender. I met with a landscape design guy... that will help! Definitely trim up that left tree in front; that's the first thing the designer said. Sadly you can't see the awesome redwoods (3!!!) we have directly to the right of the driveway, on a little hill area. We are gonna uplight those for sure! So we do have some good stuff to work with.

- brick: I'm taking it all out. Going with concrete pavers instead. Going to stucco over the brick chimney, in the body color of the house.

I'll post an iPad concept update... as soon as I make it... :D

What's the latest update with your landscape project? Got any pictures?