I think the house needs to decide what it is first. The right is a modern addition and the rest is colonial wannabe not exactly perfect together. So what do you want it to be and first what is your budget. Anything is possible with enough money.

I think just taking the shutters off will bring the two parts together. Update the landscaping and add an ornamental tree on the left side out in the yard.

Do you have a budget range in mind? Just paint? New roof? Landscaping?

No budget exactly. I’m not crazy about the half brick half siding. Looks outdated to me. Maybe looking for something more modern

You can:

1. paint the brick and siding the same color

2.paint the brick a wash of the same color as the brick

3. paint the siding a darker color such as dark blue or dark green

4. regardless of how you paint, definitely punch up the landscaping in front of the house

I'm no architect, but the columns for your pediment look a little undersized, given how high they reach. Any chance that was an addition at some point? It doesn't really go with the colonial look the main body of the house has. If I had unlimited funds, I'd address that. Most colonial revival houses have a one-story portico.

Edit to add: As for the modern addition on the right side, I'd probably just introduce some fast-growing trees or bushes to diminish its appearance from the street.

In order to "marry" the two different wings of the home, I would remove the columns, pediment and shutters. Behind the pediment, the left side appears to be more of a Garrison Colonial style, while the right is contemporary. Then upgrade the landscaping, filling about 1/3 of your yard next to the house with well designed planting beds and some trees. Edit: recycle the shingles from the pediment to the new roof. To bring the left side in line with the Garrison Colonial style, add a trim piece all across the bottom of the siding as seen here.

a house of six gables - the exterior · More Info

I would remove the shutters and paint the brick the same colour as the siding. Also paint the white vertical corner trim pieces on the edges that same colour. If possible, beef up the white trim around the left side windows to better match the right side.

you could always paint the brick and siding white, redo the pediment, and the add-on portion

Shutters off so the right and left are better matched. Remove the portico and pillars entirely. Look for a different style portico for just over the door, something like the one in Beth's first photo. Here are others:

This one has double pillars:

Front Facade · More Info

This one extends the entrance forward:

Garage and Connection · More Info

Notice the substantial pillars and the way landscaping on each side extends the house:

Garage and Connection · More Info

Devote most of your budget to a landscaping redesign that brings visual interest forward and balance out the mass of the house.

https://www.houzz.com/discussions/5741384/1960s-garrison-colonial-update-black-windows-metal-roof-farmers-porch#n=8

Here's a nice solution if you don't like the overhanging second story; add a porch!

Who thought that ad on was a good idea no attempt to make it blend in !

I am hearing the owner wants to move toward the modern not away from it so the add on needs to be in inspiration. I agree the columns are too skinny for their height. I am not a fan of painted brick but seems the most cost effective solution. Or just removing shutters/portico/columns and beefing up the trim on all the windows. It would be pretty plain jane modern then.

"Updating" seems to be a catch all word for changing something that we don't like. Rather than try to turn a colonial into something it isn't, the best curb appeal will be achieved by embracing what it is. People should buy a modern home if they want modern.

I do agree with removing the shutters (since they're mounted wrong) and fixing the column/pediment situation will do wonders, though.

Ignoring the large element on the right for now, the house is a Garrison Colonial with stripped-down Neo-Classical columns and pediment. Unless you're comfortable with the inherent architectural contradiction and since it would be virtually impossible to get rid of the second floor overhang, one solution would be to remove the pediment and columns, add the missing trim board at the bottom of the overhang, use a more interesting paint color on the upper part and possibly paint the brick. To add some interest to the roof you could add some dormers if the roof slopes enough to allow it.

Perhaps the large element on the right including its trim could be painted dark color.

Painting the brick the same color as the siding would help unify the fascade but, as everyone will tell you, once painted brick cannot be stripped and restored to its original look. I agree with other posters - the two portions of the house do not live easily together but painting the entire house one color might alleviate that to some degree. I also agree that the gable and columns are out of place. Removing is an option. Another option would be to enclose the area under the gable to create a bump out. This would give you a bit more room on the house interior. Good luck!