you already have the dark windows, so that's good. do a medium gray roof. that color will go w/everything. Do you like dark? if you did the dark siding and added some wood composite siding, it could look a bit more modern. I notice you have some cedar up under the roof eaves. that would be cool if you could do it elsewhere on the home. similar home style with a darker green siding and the brick lighter gray (btw, these all have the stairs like you have. check out some of the landscaping around them wood doors, and all the siding running the same way. Another gray with shingle siding. arbor over garage. cool landscaping here's a before and after where they painted the brick and did the black windows and added some wood siding accents

For what it’s worth, a neighbor-friend on a street where I used to live put their house on the market a week or so ago, and I looked at the listing, which included a link to street view. I happen to scroll a few houses further, and I noticed that one of the houses on the street — a colonial like yours — had been ”updated” to have black windows, modern door, plain columns, sort of like picture Maureen posted. It truly looked awful, especially since the surrounding homes all still have a coherency of history about them (houses typically 100 years old on the street, not special, but just typical of an era, with variety of victorians, colonials and 4-squares). I think the people who updated their probably knocked $100k of the value, possibly more. It looked like the house had a fire or a tree fall on it, and they couldn’t afford to rebuild it to its orginal charm. HOWEVER: When I actually lived in that neighborhood I was taking a walk one day, and I passed a small group of people meeting on the sidewalk in front of a 100-yr old colonial house where the BACK SIDE of the house had been completely knocked down and rebuilt in steel and glass. I overheard the architect (who was standing right there) explain to the 2 other people) how when they toured the house, they should notice in particular blah blah — I just stood there, shamelessly eavesdropping, and when they started to walk toward the house I tagged along — I think the architect didn’t quite realize I didn’t know the other 2 women. Anyway, the back end of the house was super contemporary (it faced into a hill, so there was no problem with the all glass walls). Why don’t you leave the front of your house as is and do the back as MCM as you wannabe?

New modern art, rug, lighting, window shades and great looking sectional sofa that all work with the warm floors would get you off to a good start. It's not the mantel that's the problem, it's the enormous TV that needs to go on the side wall and the man cave sofa and chair. Work with your trim, floors, and cabinets but go a little out of the box with great well-designed fairly modern pieces. Go on Craigslist and see if you can find a wide console for the TV. Search for "midcentury or MCM console, sideboard, dresser" Art for over fireplace in this palette of golds, touch of blues, gold/orange, green you can echo in rug and pillow. Go online to Etsy and just put in "abstract paintings" and see what comes up. From your art, choose a rug--something like this with golds but with green from your art. Sectional sofa in camel/gold leather. Not a bunch of things in this photo--low lines of sofa; window treatment; great piece of art in corner; graphic rug You'll want a round coffee table to tuck into the "L" if you get a sectional. Go with wood with maybe a pullout to use from both ends of sofa. Get modern nesting sides tables as well so you and guests have a place to put down a drink while you're either looking at the fireplace or the TV --Get a modern round white tulip table for your kitchen dining area. It's too dark in there to be inviting. Bigger tulip table than this, but keep your current chairs so you don't have to change everything. Save your money to put same window treatments--roll-up shades in your bay window. Ikea has a decent sized tulip table. This shows how great any kind of dark chairs look in contrast with the table. While you're at Ikea, get a modern white pendant to drop over the new table:

Don’t paint the handrails. Strip and re-stain if you want to change the color. I’m not fond of espresso or gray paint on interior wood. Semi-transparent or semi-solid stain is what I would do for those darker tones. If the baluster openings are wider than 4”, consider replacing them and adding more balusters. If you go with straight 1.25” wood balusters, you could put them closer together (about 2” apart) for a mission-style look. An added advantage is the close balusters mask the dirt on the floor that you would see from seated eye level of the living area. Black iron balusters 4” apart might be easier. But you may have to work with the holes in the base or create a new base. (I actually built a raised base because of the floor dust issue.) If you are worried about all this being too dark, you could paint the existing balusters as a test with your new flooring. I like the handrails and newel posts. They could be re-stained to match the beams. It’s hard for me to tell what the wood colors are throughout from one photo. And I’m not sure how the slate floor would look and how the stair treads and risers would be affected. Figure out everything before doing anything to the guardrails. Sorry to be so ”all over the place” with this. I have opinions because I have struggled with this before - there is just not enough information in the one photo. All adjacent rooms need to be considered.