Are you considering cladding changes? Or just a little sprucing up?

To start, I'd work on making the entrance more inviting. Change out the light for something more substantial. Add pretty address numbers. Expand the stoop out to the outer corner of the sidewalk. Put a bench near the door.

Then add some shrubs and perennials both near the house and on the outside of the sidewalk. Hire a landscape designer to come up with a plan that you can implement yourself over a few years.

If you want to go further, remove the shutters. Then re-side the upper area in shakes (there are some really nice vinyl ones that look very like stained wood) and the rest in a coordinating board and batten.

Leave the shutters but paint them dark gray. Then invest in some substantial landscaping. Landscaping can make any plain home look significantly better!

Little or not structure change is tough! 3 things bother me with the house, the front door looks like a mini-entrance, the eye is drawn to the lower area where there is no windows or shrubs, and the sidewalk looks like a bunch of Chicklet gums were dropped off. Definitely consult a landscaper. They will advice you to rework the walkway, Bring it out further from the house, perhaps plant some evergreen type bushes to camouflage the empty area . More trees to soften the corners of the house. If you had money to change the entrance somehow, a pergola or peaked roof over the entrance.

My plan so far was. Add white trim to corners. Paint shudders gray or black. Put in a new front door painted pale yellow or black. Add garden boxes to windows. Add new light fixture.

Also sounds like I really should see a landscaper, new thought,

Thanks for the pergola idea Sue, do you think the things I just mentioned would look well with a small pergola?

Would garden boxes make the house look to squat? So to speak.

Agree with removing the shutters because they don’t fit (wouldn’t close over the windows). Also agree that a larger front door would create a more substantial entryway. And landscaping, definitely.

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Notice that neither have the shutters?

Those shutters on your home detract from the exterior. Please remove the shutters and beef up the window trim. Please read this article about shutters so you can see why they don't work: http://www.oldhouseguy.com/shutters/

You just don't have the right amount of room next to your window for properly sized shutters.

The others are right about the landscaping and a landscape designer. I think your walkway could use a little bit of help, but the basic idea works. Just expand the walkway so it is wide. The landscape designer can help with that too.

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Are you going for a cottage style home? The window boxes might be difficult to maintain well (with plants for your area). Also the door you have selected looks doesn't go with the style of your home IMO.

I like the white corners, new door, and gray shutters. Window boxes add interest. Fix the landscaping and you have transformed your house!