Where are you at? As in generally, so folks can help you with growing suggestions. Do you get snow that you need to anticipate plowing for? How much upkeep do you want to have in your yard for plantings?

Thanks for asking. Northern Michigan-snowy cold winters. I’d prefer somewhat minimal upkeep (I’m 50+ and work FT). I can’t afford to have trees planted around my entire property all at one time, so thinking I need to do things in increments or create smaller private spaces. I don’t know where to start. 🫤

Fedco has some good prices on trees. Their ordering is still open (closes soon).

Small Trees and Shrubs - Fedco Trees (fedcoseeds.com)

I'm not a big fan of forsythia, but it will root really quickly. Buy a few shrubs and pin down a few branches and you'll have more plants in a year or two.

I would focus on where you want privacy first. One or two small trees or shrubs might provide privacy for windows.

Which no real idea of what you want, I'd put in a few plants at the corner near the pole.

Go to a local nursery and speak with their designer. Tell them you want to implement the design over time (as budget allows). Sometimes there is no charge if you buy plants from them, sometimes a nominal fee. In your situation I would want a plan first, so you are not placing things willy nilly around your yard. Fences are expensive but I think a rail fence across the front and down the right side will your property some definition. The next priority would be something around the front deck (looks like that is your "entertaining/relaxing space.

Move the seating area to another side of the house and put up some privacy fence panels. Plant trees and shrubs as you can afford. I don’t know where the logical place for a seating area would be because you don’t have exterior doors marked, but it’s not the current location at the front of the house. You can use fence panels to block the view without doing an entire enclosed area. You can remove the panels as the trees and shrubs grow.

As @shadywillowfarm suggested, you could do a privacy screen with only a few fence panels. Then when hedge grows in you could decide whether to remove it or not? Much less expensive than fencing entire property. We love the evening sunset from the front of our house. But our neighbor has cameras aimed at all the neighbors now and monitors all of us 24/7. We installed a couple of screens like the photo of the sloped front. So much more peaceful.

Costco Traverse City should be getting their yearly spring supply of Arborvitae. Good size at $35/ea. You can add more every year. These won't work if you have deer go through ypur property.

Arborvitae.... Not exactly interesting.

A few overlapping drifts of a variety of trees and shrubs, NOT rows, would do the job.

Ok, Mi with a hard ditch along the front line of the house. Whatever you plan on along that property line to the corner, you will want to plan it for on the house side of the ditch. Leave the entire ditch to road area clear with just grass like you are doing now. It looks like you can get closer to the road on the bottom of the pic, but do allow for plow clearance depending on how much snow you get and visual clearance at the corner for drivers. Check with your local municipality about if there is setbacks or height reqirements with plantings or fences.

Otherwise what I would do. Plan out an entire border along the two road sides. Plan it in segments. Like the corner itself and 2-3 sections along the bottom side of the road and a couple on the house facing side for year one. Maybe some bits of pretty fencing, plantings. Start breaking that long view. Next year do in more sets, fill in spaces with drifts to break more sight line as you go. The first sets you do help you line up the rest of them in future years. If you want, you can put in moveable fence panels to shift around too as things grow in or put in permanent panels as part of the border. It can take a few years to really fill in an empty line, but if you start with a plan it can work. If you just go in piecemeal it can work much less successfully.

There is of course a lot of other things that can be done to break up the property and make more intimate spaces. I'm just suggesting to plan out the outer edge of it to start with. You can always build inside that if/when you want.

There are a fair number of places to get large quantities of baby shrubs cheap. Fedco, Musser Forests, and your local Soil & Water Conservation District. The selection is limited, but the screen could be added to with more interesting things over time.

Thank you all for the recommendations. I wasn’t expecting such well thought out ideas, specific to my situation. This is so helpful!

If you place one of the suggested fence/screens along the garage path (yellow line), the area by the fireplace flue would have some privacy for a seating area (yellow circle):

You have a huge property and your main sitting area looks like it's at the front of the house. A pergola would give you a sense of privacy with the slatted ceiling with a side privacy fence on the corner side (you can grow vines in that section on the exterior side). Plant nice flowering shrubs on the front part along the patio on both sides of the path that leads to the house.

@tracefloyd thank you-I think this could work & wouldn’t completely block my view of lake & woods

@lisedv thank you. The pergola would definitely add dimension & make the front of house less boring!

I'm so pleased....two more visuals for you. Adjust the fence accordingly for the view.

It's hard to get perspective in my renders...the chairs are inside the fence in one render, and no where near it in the other. But it will be fun to think of what style and how to articulate the fence on site.

The screen could be a curve for softness or in large zig-zags to create zones for seating or plants...or the lamp post and tree.