I would lighten the paint color and after that landscaping!!! Add something to ground the house (bushes and plants) between the 2 windows were the gap is id put something with some height to fill that space visually.

I would lighten the exterior to gray or grayish blue, change the front door color so it can be better seen, and add deep curving landscaping beds to nicely contrast all of the straight lines.

Paint it. Prune the tree (heavily). Break the long expense of facade with low and high shrubs. Build up the front door with pots, urns, and an improved walkway that draws the viewer in.

Do NOT waste time or energy on the things you’re mentioned as having been improved (roof, siding, etc). They are fine. Work with them.

Before you paint the whole house, try painting the trim & front door first. I think there is too much contrast between the dark brown and white. You could go with either tame or bold: a creamy beige would help tone it down or you could go the opposite and use a bright blue. (brown & blue can look nice together) Some colourful big plant pots & out door furniture on the porch would be nice, then when time & budget permits, a generous planting bed of small shrubs, perennials and bulb to the right of the porch would de-emphasize the plain wall there. Not knowing your planting zone, it's hard to suggest actual plants but go for a mix of evergreen & deciduous shrubs- your local nursery can give you ideas which will do well in your location, or stroll about the neighbourhood and see what you like in other people's gardens.

Window boxes might look nice

Landscaping, & lots of it. Seek the help of professionals if you need to.

Your home is lovely. I wonder if a little landscape of some simple hedges can help. Hedges that will grow under those small drive by windows on the right side of the house... And maybe white painted bermuda shutters to give the illusion of a large window.

A little landscaping can help with window boxes. HGTV

Shutters might help. But they added a portico over the entrance. That could be very pricey https://www.pinterest.com/egarcia0552/1950s-ranch-home-makeovers/?lp=true

See the pink bushes might add a little interest

Sometimes a bermuda shutter could add symmetry and create the illusion of a larger window.

Landscaping. I think I might keep it simple and bring in a few large pots/planters around front of house + some lighting on the grounds.

Aw, your house isn't ugly, it just needs to be dressed up for the party! If your budget allows, pay a landscaper for plans and do the planting yourself. Do not underestimate the value of a well designed professional plan...it will make a huge impact on your space. Best wishes!

Landscaping!! Most houses are ugly without it. We have a local nursery where I live that will actually come out and draw a little picture for you for free...they actually use landscape architects too. I’d call local nurseries and see if they offer a similar service, even if you have to pay a little, it’ll be worth it. Usually a big landscaping company will charge a lot, but if you can afford it that’s probably going to be your best bet. If that’s too much money though, use your local nurseries, take in pictures of your house and let them help you pick out plants...and take it slow. You don’t have to plant tons and tons of things at once. It may take you a few years to get it how you want it. There’s a landscaping design board on here, and will also be a local board for your state.

It’s too bad that tree is smack in front of the house. I’m sure it’s beautiful, though. Limbing it up would make your house so much more attractive - remove AT LEAST the lowest ring of branches. Probably two or three rings is what I’d do, so there’s no branches/foliage hanging under the roof line.

I like the color of your house, by the way. You just need landscaping and maybe a nice, wide sidewalk. Blobs of green would go a long way toward breaking up the hard horizontal line of this ranch. You don’t have to go as elaborate as the sample offered above, but use that as a template.

Oh, and clean up the front porch paint and get some real steps.

Wow Doug, that’s impressive! Thank you all for the landscaping ideas, I don’t know why that never occurred to me!

We do plan on doing something with the porch and steps, the shed style roof is too low and you can’t open the storm door all the way, plus the steps are ugly. When we do that, we’ll have to do something with the vertical siding on the front bump out. Should we find a different vertical siding to put there, or put up the same grooved shakes on the rest of the house?

The large tree is overwhelming. Rather than seeming like supplemental shelter, looks like a monster ready to attack. Needs some bottom limbs removed in order to become friendly again.

A little landscaping and a new mailbox would dress things up considerably. Its definitely not an ugly house, it just has untapped potential. I agree with Yardvaark that bottom limbs of the tree need to be removed. A little landscaping to frame the driveway and the front of the house would also significantly improve curb appeal. Of course, we would also suggest adding a classic looking mailbox to polish off the look, but we may be a bit partial.

You might want to get an arborist to look at your tree. After enlarging the photo, I think there appears to be some suspect areas... before embarking on a whole new landscape, make sure the tree is sound and safe.

Not sure what color your front door is, but a pop of color would be great. Also updating a house number and some new exterior lighting. Start simple with some potted flowers. Eventually get some more landscaping done like others suggest.

Mature trees are nice to have, though this Maple is much too large in scale to your single level rancher. Better choice would be to get a Japanese maple-they grow fast, or another type of tree for your zone that matures at 12-15'. Landscaping has a huge impact on the esthetics of a home.

I would add shutters , lighten the paint and loose the tree because it blocks the front door, try a white shutters and red. yellow door with a lighter gray.

Your house will never feel pretty until you stop calling it ugly! It’s a nice house, maybe the paint is too dark and maybe the landscaping needs some work but it isn’t ugly.

“Monster ready to attack”, I like that :)

The tree didn’t fair too well this winter so we do need to find an arborist, but we intend on leaving it until it becomes a danger. It seems a shame to cut down a 100 year old tree because it doesn’t look good in front of our house. Plus our house faces west so it keeps our house comfortable in the summer. With that, the entire front of the house is quite shaded in the summer. We have hostas along the front porch but even they don’t grow very well so I will need some help picking the right plants. Unfortunately our mailbox is across the road so we won’t have a pretty mailbox for curb appeal.

The front door is the same color as the house, not sure why the previous owners did that. The house itself will need to be repainted in 1-3 years but the garage should be painted this year so I’m trying to figure the overall color scheme

I don't think your home is ugly at all. I agree that landscaping is the key to bringing out the best for your home.

But now that you mentioned it a nice yellow or red front door would look amazing!

I would love to do a bright front door!

I found th Sherwin Williams Visualizer (please pardon my sloppiness)

For some reason I don’t understand, when I accidentally clicked on the sky, the app darkened the color on half of the house, I like the right side but I’m not sure which is accurate for Intellectual gray?

So much potential! Painting the house and adding some simple shrubs, trees and perennials would definitely be a good start. Also, redesigning the front entry as you have already mentioned will add a lot of curb appeal to your house.
My suggestions would be to start with a good landscape design (or even a solid plan) and implement it over time as your budget allows. A lot of the work can be done yourself, but you might find that you are more at ease once you have a plan in place and a goal that you can work toward. Good luck!