Overall, nice batch of pictures to start with. (Wish everyone would grasp that idea!)

Thanks Yardvaark!

Now help me! LOL!

While one could make suggestions based on what-most-people-living-in a similar-home might want, it's not obvious what you want in a landscape. I suggest you begin by sharing your objectives and expectations. You can get help and guidance here, but you'll need to turn it into a plan (or have it turned into a plan by a professional) in order for it to have lasting value. One immediate tip I'll offer is to remove the bottom limbs from your trees. They'll be large someday (sooner than you think) and there will have been no point in allowing those bottom limbs to remain ... unless your goal is to have a bigger scar and more work. The ones in the photos are large enough that you should be able to walk below them without smacking your head ... at the very least.

Thanks, Yardvaark.

As I had said, "The goal is to make the area feel a bit cozier and park-like, while diffusing (not necessarily entirely blocking) the views of the surrounding homes." I feel that the house doesn't look "anchored" to the property yet (newer home) and the expanse of lawn unbroken by trees and shrubs give it a "bowling alley" feeling.

I've begun trying to get an idea of what to do out front, and I've gotten as far as the image below, but worry that I'm not getting the "inviting and welcoming look" I'm after.

I'm aware that my circles and ovals aren't "to scale," but just trying to get a plan together to give to a local pro.

I like the direction the back is going, but the front of the house is where I'm stuck. I know I need to move the boxwood that lines the front walk (perhaps moved to the base of the Maples? *circled in yellow in front*). Also, I want some type of tree placement that doesn't block the view of the entire front of the house... a bit more "formal" of a placement, but not overly so and not fussy.

The ditch by the street is full of Cattails, which I love.

Additionally, the small area between the front walk and the garage (near the front door) is a challenge. Right now, there's a pink Dogwood tree and not much else.

adding to my prior message ...

For all except the small tree, you might consider the height of the eaves to be a minimum goal. Obviously you can't remove all lower limbs below that now, but you can go to 50% the height of the tree mass, helping you work toward your goal each year, rather than waiting until long after most of it is overdue. The small tree at the front of house is an exception and must be shaped to fit with the architectural features.

A couple of things I don't care for about your landscape are the long, confining hedge along the front walk. It doesn't look bad from the street, but I'm sure it makes the walk experience less pleasant than it could otherwise be. And the rhythmically dotted shrubs marching across the front foundation. Some street trees would help with "framing the view" and the feeling of ultra-exposure.

Sorry, you mentioned goals but it's been a few days and I forgot about them.

After seeing the aerial view where you are working out your ideas, instead of getting the "inviting and welcoming look" I think you are getting the hodge podge look. It seems to me that you are assigning plants to the yard based on the ornamental personalities of the plants, but forgetting entirely about their architectural and functional purposes. Every tree is a roof and a ceiling ... a shelter. Plants can be walls, floors, barricades, land & path markers, screens, sentries, landings, gateways, arcades, upholstery, and I'm sure, more. These things can be small, or giant sized. It would be best to think about how you could use these things before thinking about the pretty details of plants. Could you use a large wall in January to "break" the fierce bite of winter wind? If viewed through an "arcade" wouldn't your home seem more "cozy". Wouldn't it appear more luxurious if the entire house sat on a low, cushioned platform-like, upholstered "landing"? There are many ways you could use plants to make improvements to the property, but just sticking pretty ornaments wherever you can find room for them would not be any better than adding a disordered mish-mosh more of building materials and furniture to the inside of your house.

"Before" ...

I already acknowledged that I didn't know what I was doing, but I appreciate you putting a finer point on it.

You haven't acknowledged them so wondering if you're in agreement with any of the suggestions I've made.

"One immediate tip I'll offer is to remove the bottom limbs from your trees."

I do agree. They've just reached the correct time of year for pruning and it's been scheduled with a local company.

"A couple of things I don't care for about your landscape are the long, confining hedge along the front walk."

Agreed. I'm in the process of hiring someone to move it for me. I am considering moving it to around the Maple trees in front (saplings right now).

"And the rhythmically dotted shrubs marching across the front foundation."
I hate that, too. I don't know whether to let it grow into a solid hedge, or remove it completely.
"Some street trees would help with "framing the view" and the feeling of ultra-exposure."
That sounds like what I want to do, but I'm too "structured" and am trying to make it look less contrived. But the harder I try to get that look, the more garish it becomes.
I love your taste, Yardvaark. If YOU like it, then I probably do, too. What would you do if it was YOUR house? You probably can see the needs better than I can!
I don't want a lot of plants that need dead-heading and constant pruning (some is ok, but not everything). I'm in my mid-40's and not getting any younger, so I'm looking for what will give great impact sooner rather than later. BIgger-picture landscaping stuff, not gardening stuff. Does that make sense?
If I'm not explaining myself, perhaps you can ask me specific questions I can answer?

You explained yourself fine. I was just looking for some agreement. Little time now but will work on something for you in a day or two.

Here are suggestions to show how you might achieve a more organized appearance. Since the property is sizeable and you need all of it organized, theres quite a bit of work for you--or someone--to do in the plan view. I'm trying to show how you might group things. Avoid small individual plants like lilacs in the outer reachers. Use them as a hedge or grove instead or use them closer to the house. Street trees would need to be set far enough back from the road to protect the cattails. In the plan, I'm adding trees to what you already have to show how you might group them. (But don't take my "plan" too literally as you might need other things arranged differently in other places. Smooth the pond edge out some so that it doesn't appear jagged. Trees are mainly at the street, house and perimeter. Leave some open space, too.

adding a plan view

Yes! I love the way the front looks! Simple and organized and more inviting.

I see what you mean about trees being at the street, house, and perimeter.

Thank you for taking the time to do this. I really appreciate it!

You are welcome. Glad it helps. In many of the lawns where people use a fair amount of trees, usually, they don't clear out the lower branches sufficiently. It not only kills the view within the yard, but it leans toward a feeling of oppressiveness, gloominess and claustrophobia, depending on how dark it becomes.

Yes, I can imagine that. I had a Sugar Maple once that was limbed up (professionally) to about 10-12 feet and it was perfect, IMO. Maintenance was a breeze and it was beautiful to see it in the yard, yet still see past it.

It will probably be a LONG time before these trees look like actual trees, eh?

It will be much sooner than you think.

I like all the ideas but I would get rid of the bushes lining the walk to the house and along the house. It's too formal. put in large flower beds, lined with big rocks. Maybe Hostas edging or ornamental grasses. Curve the flower beds around the house. Add flower boxes under the windows with lots of colors hanging down. west side needs a climbing flower to hide all that white walls. purple or blue, maybe even red would make it beautiful with a large flowers with all colors edged by ornamental grasses. Add a rock walk way around those flower beds so you can enjoy walking and seeing those beautiful colors. and where those steps up go put beautiful colored flowers on the rails and add hanging plants. and where it shows the back yard, make a seating area with a water feature. edged with more flower beds. where the bushes are torn out by the front door. put a big flower bed and where the wall is siding put a large climbing plant with bright beautiful color. Also add some large trees to the front yard with color. and add different metal flowers that adds sparkle to the flower beds