Your house looks great - I would focus on the landscaping! Graduated plantings with various heights, textures, colors....I don't understand the plantings by the big tree in the front of your house and would take out the plantings and just put a ground cover in the circle around your tree. Consider removing the shutters, and adding a climbing vine between your front windows. I would paint the porch siding the same color as the rest of your siding.

I would remove the shutters and that evergreen along the curb that blocks the house. Look at board and batten if you are replacing the siding. It is a much more contemporary look.

This is a tough time of year for all of us, including our homes. None of us are in bikini shape. 
Some nicer weather, greener grass and a little sunshine will make everything look better. 
I agree with the others, get rid of those plantings that have lived long enough they're past getting in shape. 
I can't see your porch well, but yes, have it match the rest of your siding and make it a place to come home to. 
Colorful plantings will make everything better.

Is that brick on the porch? There is so little of it, I'd be tempted to match it to the new siding color. Romabio can do that for you with masonry paint, and you should look into James Hardie for siding. The top trim on those two front windows should be removed and they should match the look of your other windows. Do away with all of the shutters and upgrade the builder grade front door to make a big difference. Redoing the landscaping is where you'll get a real change in the look of your ranch.

Thanks for the feedback. Those plantings by the tree are a bone of contention - I hate them but my husband thinks them quite wonderful.

If you are doing new siding, I would remove the shutters at least on the double windows, and the decorative lintels over the windows, they are the wrong style for the house. I would also remove the railing, I don't think you need it with a porch that is so close to the ground level.

I also agree on removing the decorative trim on the 2 windows. I would choose a grayish blue or grayish green for your siding - and think about painting the shutter something other than black, say deep navy if you go with blue siding, or deep green for green siding, and use the same color for your front door. But, black will also work, especially with blue siding.

The half moon window door doesn't match the house style, so I would replace with a 1/3 or 1/2 light door with 6-8 panes (something like this).

I wouldn't necessarily change the brick or the railing, other than to perhaps paint the railing a complementary color or the same color as the door. I think they both add some charm and interest.

You will definitely get the biggest bang for your buck with better landscaping. Perhaps you could move the shrubs and small trees to incorporate them into a new design. I would build a short raised , somewhat curvy bed with brick or stone across the front for a start - just high enough to hide the foundation block - and pull out all of the stumpy evergreen bushes.

You may have a local independent plant nursery/garden center that will do a plan for you at low cost, or even free if you buy your materials from them.

I wouldn't spend money on new siding unless it's old, damaged or discolored on sides we can't see. People post pictures of some ugly houses on this forum but yours is not one of them. Personally I don't love the yellow front door, but if that's your favorite color, you do you. I would do red or a bright blue. Landscaping needs to be refreshed every 5-10 years. When plantings are new they're too small, then at some point they become too big and/or leggy looking and have to be either trimmed way back or just torn out. Some bushes will tolerate being whacked, some won't.

If you want to do new siding because you're tired of what you have or you didn't choose it because it wasn't your house then, post some pictures of things you like so we can get an idea of what you're going for. Houzz has thousands of pictures you can choose from.

The house is nice. It has plenty of detail. I'd remove the shutters. Landscaping never looks good this time of year. Reassess in the spring. That weeping evergreen was an expensive, specimen tree. It could easily be the highlight of your landscaping.

I second the nix on new siding unless needed.

Agree…why replace siding? If you have not been in your place a year, rule of thumb is one full cycle of the seasons before changes…other than stuff that is obviously dead or dangerous. Take photos frequently. Then you can start to think about plants. Think about hardscaping first…paths, patios, gazebos, lighting etc. Then, trees, then shrubs then perennials and ground cover. But you don’t know what you have got, at the moment.

I don’t know why you would remove the shutters. i like them.

I like the siding and your shutters. I would put siding over the brick near the porch area. Then take a step back and see what you think. I think the porch railings seem a bit busy, but they may look better against the grey siding instead of the red brick.

Paint the front door and get a few proposals from landscape designers.

If re-siding or changing the paint color, perhaps a sage green would work with the brick?

I actually like the wider siding on this style of house, does it need to be changed because of condition?

I also like the shutters. While I understand some people are purist about shutters…on the other hand these add a lot to the look of the house even if they are just decorative. I think the house is going to look rather stark without them.

I think the house itself is adorable. Love the lime green door! (Technically, shutters should be wide enough to cover and protect the window and the window frame they are accenting, i.e. each shutter would measure half of the full width of the window plus frame.). The problem is the tree, which needs a good, (hopefully professional, if in the budget) trimming, and the droopy shrubby evergreen things next to the tree area. (Water will help fix the grass.) I would add some bulbs for Spring color in the planting island toward the sidewalk and the plot next to the house when feasible, or maybe some perennials which work in your planting zone. I hope both of the trees burst with leaf buds pretty soon….better yet, flower buds! Is that a tall lilac near the corner of the house by the walkway?
Do yourself a favor and get one soft-cover basic gardening book. It will help you identify what you have and tell you how-and-when to trim them. Allow the small rounded shrubs to grow into their natural shape and perhaps plant some flowering ground cover around them for color. Ask the nursery person for suggestions for contrasting plants.

Thanks for all the helpful feedback. The siding isn’t in bad shape, it’s just dated, drab 70’s cement siding. This photo gives a closer look, and also a view when spring bulbs add color to the landscape. Budget isn’t an issue, but I want to invest wisely - in landscaping, paint or siding, a new front door, and better sized shutters.

Changing paint colour and new shutters seems like a good investment. If OH likes weeping fir, you could pay to move it.

Didn't have time to read all the comments, but it is what it is! Landscaping would be the best and most cost effective thing you could do. Hire a landscape architect for a consultation and possibly a planting plan.

What about taking a few photos of the small 'trees'/bushes in the front yard to a local garden center that has a landscaping department to see if the bushes can be moved and still survive. In some parts of the country NOW is the time to do that. You may still have snow so the time to do that will be later in the Spring. The large tree is a plus but those smaller ones are detracting from your home. If they can be safely moved your husband may agree to that compromise.

I think your gray/black/white color scheme goes very well with the age of your house, and I think the black shutters work, but the yellow door and red brick are not the best fit together.

Do you think your husband would consider painting the brick the same color as the siding (see Celery's rendering)? If he doesn't want to move the large shrubs in the front yard he probably won't buy into painting the brick but you never know. Another option would be to choose a better color for the front door. Even white would look nice although I have a hunch you'd like a more interesting color.

This is a very good point about moving stuff. It’s definitely done when the plants are still more dormant. I’m not quite sure what your zone is but you don’t want to do it in the hot weather.