Hope, you have a very solid house that with just a little work can be great. First of all I would not paint the brick. Use it as the base for everything else to get a cohesive look, plus painting brick takes a no maintenance product and turns it into a long term maintenance issue.
Here's a list of some things I would do, and why:
1) Get proper size shutters (old ones are too narrow) and put them back on the house, but only on the two windows on the left side of the house. They don't work on the large window under the porch.
2) When you said lake house and I saw the porch columns my immediate thought was, "That round column doesn't say lake house to me, a square wood column fits more with the lake theme." I would probably only do a wood column, unless you can match the brick. If you add stone you're adding another material and you don't want the facade to get too busy.
3) I would paint the gutters the same color as the trim. Right now that dark brown makes them stick out visually and you don't want them to be seen.
4) Paint the front door a bright color that draws the eye. Right now that dark brown just makes it look like a dark hole on the front of the house.
5) I would go ahead and "bite the bullet" and take out the existing landscaping and just start over. Trimming the existing is going to expose a lot of wood.
6) The one other thing I might look at is painting the trim a different, more earthy color. But that would be only if you really don't like the existing trim color.
If you're interested in seeing some of these and your ideas virtually check out my web site, Creative Visual Concepts. I can show you how your house could look with these and other changes.
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