How do you define "modernize"? And a couple of pictures taken in daylight will let others see the house better.

Dunno about the house, but what a pretty tree!

Since you are planning on some major updates in just a few years I would probably take off the green shutters, paint the window boxes white, make sure to plant them in the spring and cut back or remove the big bush at the front and call it done.

Better windows in few years will make a big difference.

For some reason that big ugly bush makes me think of the 1970s. Please get rid of it. The trees are beautiful. Yeah, I don't know anything else.

Belahn-It probably makes you think of the 70s because this house hasnt been touched since then :)

the bush is definjtely going, as are the purple rocks.

Btw- these pics were taken in daylight . yay for NE winters ha

Are you replacing the roof? If yes, pick a modern color (dark?). If not, paint the siding lighter, paint your shutters and facia, change or paint front door, and change that old garage door. With red brick, I would stick with a farmhouse look: dark (if not black) facia and shutters, light siding, and white garage door with a beautiful hardware. Or, light cream siding, brownish or even red shutters and red garage door. if not changing garage door, paint the trim around it. You burdget will dictate what you can and can not do.

Wow, what a cute house! I would keep the shingles. They’re prettier than newer options, IMO. A new garage door and windows are what I would focus on. The brick is fine.

Remove the ugly shrub and ALL the shutters and window boxes. That would include the shutter effect around the front door. See about cob blasting the shingles to see what you have. If you don't like them after blasting, prime and paint them to match the siding around the corner. What IS the siding around the corner from the shingles? Can you replicate that or is it undesirable? Is it paintable? Simplify, paint and then focus on new landscaping next spring.

Deco, those window boxes are the love of loves! Beautiful bulbs will make anything else disappear (almost.). The shrub, on The other hand, HAS to go.

Laraisaacs, I doubt anyone without two green thumbs would upkeep those boxes and they look very shallow to me. I like to put pots in them so they can be switched out seasonally or if something starts looking too scraggly or dies.

Regarding the window boxes, have you lived a full gardening year with them yet? I agree they look too small to be practical, especially the upstairs one. Small bulbs might work but they're only there briefly in spring. Window boxes are quite a challenge to keep looking good all year round even when a good size.

The shutters are too small, so either update them to proper shutters or remove them. The cedar shingles will hopefully look MUCH brighter once power washed. Then I would have to find a way to condition them, I am not a fan of 'weathered' cedar silver look. The 'modern' FAD is to paint everything the same color, shakes, brick; paint it all. That gives you a maintenance nightmare FOR THE REST OF THE HOMES LIFE. Right now it is "maintenance free" meaning no painting--if you like the shakes that is. When you replace the windows, will you make any of them larger? I would say this home needs larger windows pretty much in every spot. The front door has a country detail that I don't think flows and the garage door appears to be newer and really BRIGHT next to the rest of the home. Pick one trim color. I see green on the windows/window box and white on the garage/porch/soffits. White all around might help lessen the start garage door. The window boxes may be a challenge. My DH is dead set against them. How is the siding holding up behind them? The brackets they are hung with on the brick in particular might not be easily ignore once the boxes are off. They are a quaint IDEA but the reality of keeping the watered and freshened makes them a lot of work.

Thank you everyone for your thoughts/opinions!

1. i have not lived there through the seasons but the window boxes do seem shallow & the narrow.

2. i hate the shutters on the front door but theres no brick behind them so i have to either keep them or replace with something else

3. i love the cedar but hate the brick combo. maybe ill feel better about it once we powerwash.

4. the rest of the house is abestos yellow shingles so the entire house needs to be redone, thats why im not opposed to painting since its going to all come down eventually

5. roof is 2 yr old

the house wasnt touched since the 70s inside, inside needs to be gutted so we are trying to update the outside in an affordable way. i love modern farmhouse exterior but not sure its possible with this style colonial

Yeah, those windowboxes are foolishly-sized. Remove and toss.

Omg, that is a ringer for my first home on LI, asbestos shingles, dark wood trim and absolutely totally 70s on the inside. The homeowner that we bought it from thought is was fantastic. I was 25 and full of energy and after gallons of white paint on the inside and new floors it looked pretty good. Outside we changed the windows and made them larger, put siding over the asbestos shingles it was like ’96 and those ugly trees were all the rage so we just kept them trimmed. We sold it a year and a half later for a pretty good profit. Nobody wanted that house when we bought it because it was hard to see past the ugly 70s interior/exterior . We ended up building a new home with a lot less to do.I have to tell you that it is possible to make that home something your proud of without spending a ton of money. Hopefully you can get some good advice.

I actually like the color combo on the back and side of the house.It's interesting that it looks almost forbidding on the front and pretty cheerful around the side. Maybe just paint the shingles the same yellow if you are going to replace them when you do the new windows.

M Riz - were on LI!! The whole house inside and out needs a lot. Were trying to prioritize the inside and make it livable.. right now it’s not. 🤞🏻

Palimpsest - I love the country look of the back but you’re right it’s sooo opposite in the front!

Thanks for your comments!

You can do this… room by room. keep everyone updated.