I think I'd paint the brick and leave the stone pillars. Paint siding and brick one color.

Choose a taupe/beige.

Replace your traditional sconces with something more contemporary.

Do you like the porte cochere? You could dramatically open up the front of the home by having it removed.

Thanks for the input. Definitely want to keep the port cochere (we live in upstate NY and get a LOT of snow!). the interior of the house is very open and contemporary and utilizes a lot of blueish-slate, mixed with wood. I like the organic modernism inside but the outside just doesn't jive. Updating light fixtures is a must!

here's a closer-up pic of the entryway.

Yeah, I think the brick looks very busy. I think paint it a couple shades darker than the siding color.

When time to replace your roof, a charcoal gray roof would be more contemporary.

Redo front doors as well...too traditional.

Yeah, I actually like the stone and sort of hate the variegated brick, which is the finish that reads most dated to me. I *hear* that current paints or brick stains are much more durable than their predecessors, so I think I'd join mmilos in saying paint the siding and brick the same tone that will leave the roof and stone as accents.

Here you go.

First things first. I love the stone pillars, I would start there and make eveything work with them. The overall colour scheme is too tone on tone with no focus.

-Painting the brick a dark tone, It is tough to say, but would a dark blue (SW6237or SW6244) work with the siding, on my monitor it does. This will the pillars pop.

-change the pillar lanterns to stainless or black down lights.

This will give a more clear idea of where the entrance is and will give a nice architectural design. I would even consider adding 2 up landscape lights with narrow beam spread to the 2 center pillars and the brick flanking the entrance.

-Change the lanterns on either side of the door to and up down light, Again will define the space.

- front door, Thermatru Pulse collection. Get these painted in a colour would be awesome.

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The brown roof is intense, but I think that it is just big, in any
shingle finish it is just going to be a lot. I do agree with mmllos the
brown is not as consistent with making the exterior more contemporary.

What I see right off the bat is the need to minimalize the existing roof. The easiest way to do this is to build a dormer. This dormer needs to spread clear across the front of this roof, with the bottom of the gable coming to within 2'-0 on the ends and the center of the gable around 8'-0. Fill this area with glass using a commercial window installer. This storefront glass will give you the modern look you are looking for. Good luck! I know that you said you couldn't afford much right now but this is for future reference.