What's your budget?

Well, nothing too crazy as we are renovating inside as well. I'm more curious about what I can do immediately.

Do you like the colonial look?

I am about to transform my colonial from this:

To this

Not sure what's behind the left side windows but you could replace with full length, paint the exterior. I'd remove the shutters as they are pencil thin in comparison with your windows.

I think with your roof color and front door a steel grey would look sharp.

Nothing wrong with keeping he traditional look though. If you keep the same size windows on the left, you could possibly paint the lower trim portion to match brick or add some decorative colonial moulding underneath to give it more dimension. If you wanted shutters, make sure they are close to the same width of the windows. I'd paint them black. If you are dead set on keeping your, paint them black. Work on the lawn and plant plenty of colorful plants.

Thank you for your comments Eric!
In all honesty, I prefer a more modern look. However, I'm not going to fight the style just yet!
The roof is new so brown it is.

I'd like to replace the front door with something less traditional but I'll bet the last option would be best.

If I paint the shutters dark, the door and garage should be the same, right?

I wanted to add more photos of the interior, maybe for greater discussion.
These are with the previous owners furniture and colour schemes!
I'm a fan of cool tones. I despise beige.

Previous image, living room.
Dining room, family room & kitchen, sunroom and foyer.

I think you'd be better starting a new thread for the interior, as well as... actually asking a question about those pictures. :)

I would suggest you remove the bed closest to the sidewalk all together and re sod or re seed that area. Doing this will make the landscape a bit more cohesive and allow the tree behind it to be focal. I would also suggest removing the tree against the front porch and planting that bed with several evergreen shrubs that will provide year long interest.

A good place to start modernizing the outside of your home is the windows. Modern homes typically have large open windows. Have you ordered them yet? The shutters are best to be removed. Your windows are too wide for shutters. Maybe it is just the picture but the roof looks grey, not brown. Look around the site and find a home inspiration for something you'd like. Obviously the brick is most likely to stay so try searching red brick ranch.

If you like the 1st or 2nd picture for the front door, I would find windows in a similar or coordinating style and no shutters. Without shutters they could be wider and I'd make them longer, too. You could then put modern horizontal siding (cedar, redwood, whatever) if you need to finish the section under the windows. However, it will look a little odd imo because of the colonial looking porch. If at some point you intend to modify that, then I'd go for the modern windows and doors anyway because they're so expensive and you aren't likely to change them. If you want modern, definitely avoid doublehung and mullioned imo. Warning: I am not a decorator and I didn't sleep in a Holiday Inn last night.

An instant fix up that would add a lot of impact would be to paint all the white something softer and more subtle like the colour of the grout. Then highlight the front door with a color to pop. Beef up the flower gardens and add some black mulch. Save the bulk of your budget for the interior.

You said you like modern, go for it. You could go contemporary/transitional. I like the 2nd door. If you are ordering windows, a darker frame, awning or casement style, simple divisions. The rest can be done as your budget allows, but, you would have a plan.

I see everything that is white changed to grey that has a strong brown undertone. No shutters. New exterior lighting. Darker downspouts.
A modern trellis style beside the garage or none. Gardens changed to fewer choices but drifts of one type of plant, mass planted.

The photos below is to show the dark framed windows and dark downspouts and mass planted gardens.

Thank you for your comments so far!
We have not ordered the windows yet but had a quote done that would just replace them exactly as they are. I'm now debating over darker frames but wonder if it's just a trend? I agree painting out the white would soften the look and I'm anxious to take a look at a few colours.
The plants are a project. There is a ton going on there and I'm planning to put some cluster grasses and hostas out front, especially in front of the white siding under the windows. Has anyone found any pictures of this area under the windows changed to something else? I can't be the only one with this!