Simple fixes that won’t need a contractor for:
Paint beige/brown trim around house and garage another color, maybe white or black depending on your style
Switch outdoor lights out for something more substantial and modern
Paint door and trim all the same color; I think a dark blue/green would be pretty

Hard to tell with all the snow. Your house looks nice to me, except for the brownish trim around the door. I would paint that the same color as the door itself. Again, hard to say with all the snow, but, your landscaping, looks like it could be improved upon. I am seeing a small tree and three roundish bushes. I would rather see, some big pots with color by the door, and some shape to the front bed, with flowering plants in it.

The shutters are cheap- looking and narrow. Toss. My preference would be to toss the window boxes too.

Like valinta said, widen the window and door trim and don’t paint ANY trim a highly contrasting color. That fad was popular in the 1970s.

What colour is the roof?

Don't have the colour of your roof but this is one option in BM's Sage Mountain with Black doors and trim giving your house an updated look while not painting your beige windows. You can enlarge the frame on the arched window.

I would keep the shutters for more detail but replace them with wider ones than what you presently have and ad a hardware detail such as a rat-tail holdback. I also suggest you replace your sconces for larger black ones (should be 1/4 to 1/3 the height of a front door).

No shutters, because your house was not designed for them, no window boxes, again your house isn't a cottage, doors white and no outlining.

What you will have is a mid century build house, looking like it should.

Add a fun entry floor:

Do not know your roof color. This bronze/taupe siding color will go good with brow or gray. Some option to go

Even with your existing pale yellow siding with white shutters and garage door with dark trim you get an update.

Love it!!

Here’s a pic in the summer. It’s a strange house, as when you walk in you’re downstairs & go up to living room/ kitchen etc.

Now…what to do with ugly living & kitchen? Obviously all this furniture goes & the wood stove.

That all depends on your budget, what are you thinking? replacing the kitchen or updading it (paint, hardware replacement, counter replacement, etc.)? the island seems to be an odd shape, can you modifiy it without replacing the flooring or do you plan on replacing the flooring? As to the large family/living room, it's simply a question of choosing paint colour and working on a furniture layout depending on your needs. To give you valuable suggestions we need more information.

Would love to do it for $100k. New floors & new cabinets. Could we run the kitchen across the wall w window, move fridge there & take curved wall out completely? Can’t understand that weird wall. Then maybe a island somewhere?

Without a detailed floor plan it's difficult to give precise suggestions but seeing the size of the room I'm sure there are possibilities to enlarge the kitchen area. As to the curved wall, I don't see one unless you mean the one with the angles which I'm sure can be dealt with in some way especially if you plan to replace the flooring.

More pics

Yes, the angled wall. Really appreciate everyone’s input! The vaulted ceiling makes it worth a try to bring up to date. What color would you paint walls. Kind of tired of gray walls 🥴

Not strange at all...a nice raised ranch appeals to a lot of people.

I think, it needs a little updating on the interior, and the peninsula would definitely have to go, but all in all, it is a great size, and new flooring where the carpet is, and a new paint job, and some new furniture, will make a huge change. It doesnt really need a full remodel. You could maybe put an island in the kitchen, once that awful peninsula is removed. It all looks cleaned and well maintained.

What is the colour scheme of your furniture and what style do you like?

Wiithout dimensions it difficult to say if you can have an island instead of a peninsula so I show simply a peninsula that brought up to the window on the left giving you a larger kitchen. Note that appliances & window in kitchen area are not necessarily in the right spot, it's simply to give you an idea...

Well, I think that is really pretty & the window is a great idea, but would still like to open up the other wall. Maybe just have the refrigerator over there on a straight wall?

That opening at the top just bugs me and I think that wall facing out could come down?

We're not talking detail here as I don't have precise dimensions plus I don't know if there's anything in that wall behind the fridge for a reason for it to be angleled that way. This exercise is only to give you a general idea for placement of cabinets along the walls.

Color theme…subtle tan, beiges & white.

Here's a cream, white, beige theme for inspirations...

And some of the nice white paints...

Beautiful

Can someone paint & take the shutters & flower boxes off?

While I was removing the shutters and flower boxes, i tried to change only the colour of the trim on the house and doors. Sounds like you're undertaking a lot of renovations of the interior so perhaps keeping the exterior siding "as is" would be a good idea for you. You can replace the shutters with a wide frame around the windows. So here it is, no shutters, no flower boxes with white trim and doors with new large black sconces. This scheme would relate more to the beige, white, cream interior you are planning.

It’s going to be a transformation..for sure. It’s so ugly now. Appreciate your helpfulness very much! I’ll try to add after pics when we get there! This looks lovely…it doesn’t need shutters, this gives it a contemporary feel.

As above but in BM Coventry Gray...

Oh dear..that’s so pretty. I have to tell you…my daughter & I made an offer on this house today. We both love your ideas & if we get the house we would love more input & are willing to pay you a fee for your help. Would love to tell you more about our plans & the location of the house privately. Do you know how we can share contact info w/o doing it publicly?

I cannot share private information on this site but I'm willing to continue guiding you through Houzz it that can help with any decisions you have to make.

I understand. Sellers have 48 hours to accept or counter..

Wishing you luck with your offer, I'm sure you can have fun with your renovation!

Lisedv Sadly our offer was not accepted. We made a lowball offer bc the house needs lots of work. We think we need to move on…but will soon seek your advice again!

That's too bad but I guess it was not meant to be. I'll be happy to help you out again, good luck in your search for your dream home!

https://www.houzz.com/user/jenniruthjames. 

Just thought that if you don't post the next house that interests you on this same post I might not see it...

I followed you. But take a look at this (very much ) long shot & see if you think can be made to look like a Cottage.

Never mind …..my daughter says it’s a no go….to small.

Ok, I'll wait for the next one...