The good news is that your home doesn't have monstrosities that many homes have had added to them over their lifespan. It seems like basic good, solid architecture.

With the entrance set so far back, it might be possible to create another faux entrance up front by using some type of square gazebo-like structure that had some good details. On the house, I'm thinking you might be able to add some interesting (but simple and tasteful) detail to the rafter tails. And then, develop a better landscape. The current one seems somewhat plain, unexciting. Any chance on a series of slightly overlapping pictures taken from a more central point of view, including what is left and right of the property (so we can see surroundings/backgrounds)?

The gazebo structure is interesting. I definitely want to go native plants (we are in southern California) and make DG paths and focused areas with the organized "wild" look. Pics of my house below, along with pics of native California yards that I love.

It is already a cute cottagy house! You can use a contrasting paint to make the craftsman details & stone stand out.

Great ideas Yardvaark had for Arbor/trellis entrance to make the front door more noticeable, and to increase the detail to the rafter tails. Here are a couple of pics for inspiration

Maybe DigDoug will wander through and drop some of his landscape magic here.

It would be nice if there was a curvy path of some sort from the driveway to the front door path, linking the two areas.

My first thought is that the entrance area looks confining. I think the raised bed makes the area look smaller and crowded. I would remove that for an open look. Heavily mulch the area until you are ready to plant.

I would widen the path on the right side filling in the area next to the house. Those plants are blocking the view of the door.

I see where the neighbors shrubbery has grown into your yard. It makes a nice screen but I would shear it back so it was not in your space so much. You don't need anything tall in that area so maybe you could mass some low water grasses there. I can't tell if there is enough light though. Which way does the house face? This area closest to the house is where I would put the plants that might need extra attention or require more watering. I am also in California and I have a few plants that I value enough to pamper.

I like your idea for the main part of your garden. Do you want to get rid of all the lawn?

The native garden you show in the first picture is mostly perennials. A perennial garden of that size would require a fair amount of maintenance. You did not mention whether you enjoy gardening. It would be best if you could get a professional design for the that.

When I first read your dilemma it had only one response. I changed the color of your house using SW Visualizer which I suggest you try. I tried to give you a cozy cabin soft of look. Then I realized you might want a more retro look, so I tried a different color and came up with this:

Some people make bad choices in tree selection and placement. I suggest you find the species of trees you have and evaluate whether you want to keep them. If you have a nuisance tree you don't want to wait on removing it.

Also, am chiming in agreement with Emmarene's comments about too much foliage obstructing the entrance way and to sheer back the neighbor's plants and remove other tall plants. Also, think the raised bed would be better gone. It's bulk and rough rock construction both work against its staying. And widening the first half of the walk with brick strips would be a plus.

I also wish the paint colors were reversed with the body being taupe and the trim being white, shutters being possibly dark. There doesn't seem to be much actual trim around the windows. Maybe this would be developed.

a pergola extended out would be lovely- remove the square bedding area on the left by the shrubs and front door to make a larger pathway staged with a cute colorful bistro set or bench if the area allows-( you could leave the stacked stone wall on the left) - i think the house looks "crowded" with the shrubs right under the windows- i would see if you can make that bed larger by a few feet- move the plants out and soften the curves, add some other plants etc.

My thought, at first glance, is to move the plants that are in front of the house farther out from the foundation. They look too close to the stone facade.

Your house is lovely. I agree with gracie bringing those foundation plants farther out from the front of the house would make a big difference.

Wow, I really appreciate everyone’s ideas...such good suggestions that I wouldn’t have even considered. What if I removed the planters in front of the house completely and created a pergola/ deck right in front of the windows that ran the length of the front of the house and wrapped around all the way to the entry door? Kind of like the picture below except this picture has the wrap around pergola going to a side gate. Would that look weird?

Also I think I may remove or paint that stone facade. It feels dated. I may even get some kind of siding but not sure what would look good.

I would not remove the stone facade. It is subtle. Your planting at the foundation are soft. Keep them.

I actually like the raised stone bed to the left of the walkway. I think it is well done. I would start a pergola at that point and go back to the edge of the house. I would add a half gate to the front of the pergola.

I think your property would look cute with an edging of boxwood (don't know if the do well in your area) or some other low-growing evergreen.

I think paint is going to get you a long way toward the look you are going for. Here is a combination I came up with. Benjamin Moore colors.

I love where Dig Doug has put a porch! And the formal, cobbled walk makes it obvious (compared to the informal stepping stones) where people are supposed to go. I'd add one extra change: paint the door a light colour to make it stand out more. If you build Dig Doug's porch and use cream trim, that would also be a good colour for the front door.

WOW seriously I am blown away with all these great ideas. AND DIG DOUG?!!!! That design is beyond. Thank you so much for taking the time to do that. I can't believe that's my house under there. I LOVE IT AND WILL DEFINITELY BE USING THIS!! I also like the ideas of the light door. I think i may add craftsman style columns to the pergola (or would that look to out of place) and repeat the columns and mini pergola at the head of the cobblestone walkway and then do a short retaining stone wall or wood fence around the perimeter of the front yard. I also think I will gray wash the stone since its the color I don't like and then do dark gray siding above the stone with white pergola, trim, and shutters? Like this color scheme below.

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I see DigDoug did a drive by with his mad skills.

Your cottage already has subtle craftsman touches so adding onto that theme and making them stand out will work well.

I like the dark siding with white trim color scheme you picked. I am not 100% sure since I am looking at it through a monitor but it appears your roof is brown. If you need to replace the roof and want a gray colored house consider a charcoal colored roof. If you are not replacing the roof then stick to a green/olive or brown/tan color scheme. It doesn't mean you can't do gray but pick a warm gray with lots of brown and red in it. Same thing for the stone. I personally like the stone you have now and would work with it and spend the money on that portico/arbor and landscaping instead.

Thank you! We will be replacing the roof in a few years. We are courting copper but may just go with traditional charcoal tiles. I definitely want to change the rock color to be less brown and more gray.

Just in case you are not aware, here is a link for you

http://theodorepayne.org/