You have a lovely wooded lot!

Restaining the house siding and landscaping will add tons of beauty.

As part of the landscaping project, add lighting and hardscape such as wide welcoming stone steps with pots of flowers and a stone pathway to the driveway.

Thanks!

A couple landscaping photos. Consider going wider on the stone steps and maybe adding a softer curve to the front path.

I agree the steps need to be much wider a good cleaning of the shakes and then deciding if you want to have a stain on them. I think lanscaping is going to be the best thing you do,You do need to sart by having a walkway to the front door for sure.You might even be able to have a low deck under the windows on the right with a couple of adirondack chairs in a color and then tah deck could be the choice for that wider stoop

I'd start with a wider, more visible path to the front door.

If you are concerned about the roof and drainage I would spend that money first. I'm in the freezing woods, surrounded by trees, and you really want to make sure your roof isn't going to get ice dams, etc. Right? Do that right away. Call in a local roofing pro.

You're not going to be able to do much else for the rest of this year and until next spring, so you have plenty of time to think up a plan. Are you going to be able to grind down that stump? (You might be able to do that this winter.) If you can't, hope you will feel creative about carving it into a into a circular bench, or a table, possibly enclosing it into a pretty gazebo, or using it as a staggered plant stand for potted plants -- whatever to make it a delightful part of the landscape.

If you re-do the steps, considering flaring it out a bit the bottom to give it some pizzaz.

Front landscaping will help “balance” the look of your house. Winter is a great time to obsess and plan your future gardens.

I’d update in steps keeping in mind your long term vision for your house. First step is installing eaves. Second (if it were me) would be to visually differentiate the roof and the lower area. Based on conditions of roof and house, change one or the other (or both if budget allowed). Decide on the overall look you want, especially if being done in stages.

When you can, highly suggest improving entrance/adding a walkway. In regards to landscaping, head to a nursery. Bring pictures, advise soil type, light direction, maintenance level, needs and budget (can have a short and long term plan, to stretch out labour/costs).

My observation is that many houses with mansard roofs look better with siding, not roofing on the mansard floor.

A bit of paint, path, and some landscaping will go a long way.

While raising the roof might be nice, you won't want it raised much, to keep with the style of your house, meaning a lot of money for nothing (unless you have a problem with leaking). Besides, it's always hard for us to figure out how much is the angle of the roof and how much is the angle of the picture.

Are those pine needles on the roof, or can you see the shingles?

A solid stain on the siding would make it look more contemporary, or more boring depending on what you like. Is the siding in good shape?

My first thought was a steep roof but I don’t know if that’s practical due to weight, chimneys and possibly other factors. If the roof is steep enough, the pine needles fall off. Maybe snow too. It would also create a more interesting facade. It would make it harder to paint gables and dormers or reroof if no one can walk on the roof.

I’ll just throw in my favorite inspo pic which includes steep roof lines. The metal part of the roof in this pic may collect debris since it is not as steep. If roof debris is an issue, another solution is to remove trees. You should be able to find someone to come out and grind the stumps.

A portico over the front door might be nice too.

Sorry, I don’t know what is practical. It was just my first impression that the roof was too flat, for aesthetics and possibly debris.

Yes, you’re right on both counts about the flat roof slope I think. There is some metal flashing at the edge, which does help with snow, and we are planning to take out a couple of trees in the back that are right up against the house as well, so that should help with needles. We do brush/blow them off from time to time (see updated photo). For the front yard we are taking out stumps and regrading the whole thing to take out the crumbling retaining wall you can barely see on the left. (The house is sort of in a moat).

Love your inspiration pic! Thanks!

Thank you everyone for your smart insights! The photos are especially helpful to imagine something different. Will keep you posted as things develop!

Our home, built in 1939, did not have soffits. We live in a cold, snowy environment. When we purchased it, it already had a long history of leaks due to ice dams. After the repair of plaster ceilings and walls, we finally made the decision to have a skilled roofer build out our roof to create soffits. $$$$. BUT…it solved our problem. You might explore this option to prevent future leaks. Keeping your roof and gutters clear of debris is imperative, but will not solve the problem. Good luck!

Yes, that is what I’m thinking would make sense too. Thx

Yes you definately need to address the water issue I have afairly flat roof on my MCM 1957 ranch but we have overhangs with gutters to help with the huge amount of rain and snow we get each year . I know friends of ours had a roof sort of added to their home much the same as ours it just added a bit of slope and they also of coursae added gutters and down spouts . IMO worth the money to address the water issue for sure.You will need to speak to a pro who does gutters and downspouts as an addon.

Lovely setting for an interesting house. Good comments above on the roof and eaves.

It looks like the trees removed from the front yard were huge-to-medium. After you have had the stumps ground out, the soil will eventually sag and settle. It may take a year or much longer. Be prepared to have the yard regraded to get rid of the moat you mention- it may have to be done more than once as the soil settles down again.

A new landscaping plan would be good. I suggest re-using your stepping stones for a year or more as a path to the front door while the ground settles. Pouring a new concrete walkway or enlarging the steps should wait while you see how the moat drainage changes.

Is this a lake house with a view from the back yard? If so, after removing the trees that are too close, you could have some trees' canopies lifted to improve your sight lines. Or have a Phase 2 in a year or so which includes removing a few trees that block your view.

Thanks for the design drawings, simply natural. What program did you use?

Yes, we are getting the front yard regraded and will replant with shrubs, perennials and a small tree ir two. Huge trees we took out were a hazard and problem w/elec wires right in front, debris/moss on roof, etc.

Cath, I just use Microsoft's freebie Paint. It takes some practice and patience, but the price is right. :)

Your house is a fabulous, quirky vintage design that could use light restaining on the shingles but in my unprofessional opinion only really wants landscaping.

Or . . . (lower landscaping to stay under power lines):

Thanks, Melissa. Landscaping is our next step, then we’ll see. Shingles have been bleach-washed once to get rid of mildew, but they were DIRTY, so may need a second round. See before picture:

Lake house?

Thx, yes. Great advice!