To me that is a grand tree which I would want to ”capture” in my landscape design. Instead of trees, I would first look at a border of mixed and staggered shrubs, like viburnums and paniculata hydrangeas, that will be tall enough to provide privacy in the yard but clear the view of the tree and upper house. A small tree on the right - not hard up against the fence but in far enough so thst you can enjoy the full eventusl canopy on your property - seems right to me. I know you snd others msy try to plant an evergreen wall to provide a torally private enclosure but I think the result will feel like a room more than the broader landscape you can take advantage of. That's the great advantage of living in a neighborhood of msture trees and attractive architecture.

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I would do the fence first. Contractors are not known for their delicate nature around plants and shrubs. It would be terrible to plant new only to have them butchered by the fencing crew.

Are rhododendron evergreen where you live?

You are already fenced, by your neighbors I am assuming. Dense planting will conceal it. Redundant (double) fencing is a maintenance headache. Why not put the money into great landscaping? Rhodondendrons are a good suggestion. Rosebays reach 15’ in my zone 6. .

Aucuba japonica is an easy, colourful shade evergreen. Then there are numerous hollies, Viburnums, Camellias, Osmanthus, Sarcococca, Daphnes, Photinias, Chaenomeles, Buxus, Skimmia, Pieris, etc.

One tip. White flowers show up best in shade.

In 8a there is a huge selection of potential subjects.

Who put up the current fences? The picket fence is nice, the fence on the left looks like a pallet. The neighbors tree is pretty and probably gives good privacy when in leaf. When you have 2 story houses on small lots, you give up privacy. Big trees take up a lot of space and take a long time to grow.

https://www.epicgardening.com/evergreen-trees-shade/

Rosebay Rhodos are evergreen in Maine, zone 6a, formerly 5b. Plenty of rhodos are. They grow slowly though. A lovely tree that should do well in light shade is a dogwood. Cornus Florida. Not evergreen. A Carolina Sliverbell should be good in partial shade and be native to you. Very pretty.

I planted two Juniperus virginiana last spring. They work in shade/part sun. Here in Northern Virginia, they are also native which is a big plus for me. I would also add a mixed border of shrubs as kitesei suggested. American hollies will grow tall and take shade as well, although I have one that does get a lot of sun and is fine with that, too.

One fast growing evergreen is arborvitae. Every spring, Costco brings in decent sized examples for $39 last spring. You can do a clump planting or the whole row.

Rather than planting in a row along the fence, especially a blank green wall of Arborvitae, how about a generous curved horshoe bed taking in the sides and middle of the boundary.?Think garden rather than barrier. You can have both.

My walls of arbs are fabulous for blocking what was a ferocious wind and giving me privacy from the neighbors in my backyard. But I am have acres, and the arbs are tall and wide. They would eat up a lot of a smaller backyard.

I see a thriving evergreen on the left above the tall fence, plants showing reddish tones in neighbors' yards to the right and back. Maybe find out what those are? Then begin to build a mixed shrub border that will look good in all seasons as well as providing screening? Something like this? (Forsythia, cornus amomum, ilex glabra, rhododendrons shown, plus whatever your neighbor's evergreen is.) Bulbs and perennials can be added along the front.

Exactly! Just what I was imagining.

me too! The tree and rooflines ate perfectly captured in the scene.

Thanks everyone. I love all the suggestions! @simplynatural I looooooovvvvveeee this so much!