Your house is nice looking. It does need better landscaping. More on that later. As viewed from the street your roof is prominent. That means you can't go cheap on roofing. What you have now is not attractive. I don't know how many more years it will last but when it needs replaced I suggest architectural shingles in a darker shade.It will make a big difference. At that time you could replace the gutters on the front. They just don't look right. If you think you might make changes to the roof line that would be the time to do it. Actually I do not suggest making changes of that sort unless done for a functional reason. It is not a cost with good return on investment. Looking at your stoop I have to wonder how risky it is to change the bulb in the outdoor light. It needs to be wider as mentioned above. A path to the door would be very appealing. It looks like you live in a semi rural area with no sidewalks. How often would the path be used? You will have to decide if it is worth spending the money. I would make an enlarged stoop a priority over the path. What you have now is small enough to look ridiculous. It looks like you have some nice plants. They are not placed well and are possibly too close the the house. Relocate them spacing as suggested by Yardvaark earlier. Perennials will help the bed look more filled in while the shrubs take the time to grow. Some conifers grow slowly. Don't plant shrubs in front of the stoop or next to the steps. Shrubs need room to grow and you don't want them crowding the entrance. It would be worth investigating the cost of a retaining wall on the left side so the lawn could be more level. In the example above I am picturing the top terrace as being your lawn. Here is another area with a patio on the higher tier and lawn in the lower tier. You would have real steps instead of the silly bits of lawn. ^last one You might want to remove the lawn from the area nearest the road. It looks dangerous to mow and would be more attractive with ground cover which can include prostrate shrubs. Here is an image I borrowed from another site. It looks to me as if you could get a wider door and have a solid window to the left of it as opposed to a prefab sidelight. In doing so the door is much closer to being centered. What you have now is nice in my opinion and suits the house. I only suggest if it really bothers you that the gable is not centered. I am not a skilled artist so my mock up is very basic. I see that I did not make the stoop wide enough. It should extend equally from center and I know a handrail is needed too. If no one else mentioned it, a larger light fixture would be a big improvement. It looks like you just have an exposed bulb right now. On the right side I have two recommendations. First that you plant a tree that will stay smallish about 15 feet off the corner of the house. I would also suggest a row of broad leaf evergreens to eventually screen the view of the neighbor on that side.They came out looking columnar which I am not suggesting. Choose any shape you like. Do not add dormers. Do not paint the brick. Do not watch Fixer Upper.

Congratulations on your new house! Expanding the garage is an expensive proposition. Do you have the budget for something like that? The first thing I would do is remove the shutters-they're too small and not suited to the style of the windows. Then I would add risers to the steps of the porch and stain the whole thing in a color that compliments the house. Add a tall planter on either side of the door for some color and interest. You could add small evergreen trees in them for the winter that can then be planted in the yard next spring. I don't see any house numbers so I would add some vertically to the left of the door. If there's electricity available, I would also add a light to the the left of the door. For a few hundred dollars, you can have the stump ground out. Adding a flagstone walkway from the garage to the front door is a nice idea. There are crack fillers that you can use to fill the cracks in the driveway, then you can power wash it and use a concrete stain to freshen it up. I would also paint the shakes on the garage gable in a color that matches the house. Don't forget to paint the downspouts in a color that matches the house as well! With winter coming, it's a great time to sit down and spend some time online learning about what plants you could add to your landscaping next spring and summer to enhance the curb appeal of the house. In the meantime, fall is a perfect time to throw some tulip and daffodil bulbs into the garden beds to provide some pretty spring color. Hope this helps!

Following up on Addie's idea, if you want to designate an area for the pool and incorporate it into your landscape, why not? Then in spring and fall it could be your campfire area, and in winter you could put holiday decorations there. But my first item on the priority list would be a privacy fence. Frankly your house looks fine/wonderful to me but if you have no back yard and are wanting to get the most use out of your front yard with kids, etc. then start with a GOOD fence. It is not inexpensive. Then just prune a bit or refresh what you have. And for what it's worth, I think the tree looks like it is hugging your house, in a good way! Plus if I was a kid I would be up that tree in a New York minute. :) You don't need to do it all at once! And you can get a lot of plants and other things bit by bit as they come on sale or even for free from friends or neighbors who are cleaning up. Do the big important thing (fence) with a lot of planning and don't skimp on the money and the rest will come from your enjoyment of your private space as time and cash allows.

I have a California bungalow, too! Casements would be a great idea to bring those "big 3" down to scale. I think a simpler color palette would be much more suited to what you're going for. How about just 2 colors? The house one color and the trim another? Paint the "flat" areas under the eves the same color as the stucco (that dark area under the left windows, too). Then paint all the dark brown areas the same color as the "raised" decorative pieces AKA trim (a lighter color than the stucco). Is that dark thing under the left windows something that can be removed? . The shrub looks healthy. How about trimming it to about half it's current height and taking a little off the sides? You'd still have some established greenery, and more of your home would be visible. It would even out the proportions and look great! Have fun and good luck