Great place. Looks like they had something better in mind when the put in the charcoal/blue (on my monitor) colored garage door. Is it in a color from the brick? Thinking that might be a way to go on the shake siding. Replacing the wavy dormer trim and the wrought iron balcony will make a huge difference. I'm wondering if that dormer over the front door could be brought forward to make a portico and replace the awning.The front door could use an upgrade. Do the back side windows face west? Wonder why those awnings don't match the front porch one... The crabapple is beautiful, but they can be messy and it hides the house, as you said. You might live with it for a year and see how you feel then. I'm not a fan of the cedars at either end, or the clumpy shrub right in the middle. I think azaleas would work if you're in the right climate. Keep new plants dwarf so they don't outgrow their welcome.

Removing current landscaping in favor of smaller plants will detract significantly from the appearance. A few mature specimens add a venerability to a house of this vintage. and you do want something that is in scale with the full 2 story height so dwarfs are not really the way to go.

You can do some selective pruning on the crab apple (if it IS a crab....looks a bit large) to make it a bit more transparent but wouldn't remove it. Actually, the existing landscaping looks pretty decent AFAICT in the snow and dormant season :-))

Lovely house. I'm not keen on the red paint. I'd be tempted to paint it slate blue. Go to a paint website and play around with color schemes.

You seem to have a lot of trim colors going on. You have the cream by the roof, the red siding, the green awnings, brown around some windows, brown and cream around others, the gray garage doors, and what looks like white window trim in the back right. I think simplifying it to a few coordinated colors would make a huge difference. I'd vote for cream trim around all windows, cream along the roof. Slate blue siding and awnings. Places that sew boat covers can probably replace your awnings.

Most trees can be pruned and certainly crabapples. I'd remove 1/4 to 1/3 of the branches after it blooms in the spring and see how you like it. You can remove more the following year, if you like. After all, you can always remove it later. If you replace it, pay a lot of attention to the final size of what you plant there. People are often planting trees that are really too big for the spot and 20 years later, the owners are stuck deciding what to do with a lovely, healthy tree that's just too big.

Charming house. I'd be very reluctant to change the trim shape or mess with the wrought iron at risk of deleting the charm and making the house more ordinary. I do agree there are too many colors going on. A whiter trim, rather than the yellow would be easier on the eyes, but that's just my first reaction.

I am in agreement with gardengal about the landscaping. It's very well balanced for the house, just needs a little pruning by a professional to reduce the bulk a bit.

Love the red color...reminds me of colors used in Colonial Williamsburg. Some ideas if desired:

Here is a similar look with the Nathaniel Hawthorne home in Salem, MA:

I have to mention the tree first. Crabapples can be shaped for dramatic effect and that may have been the original intent with the tree that is now blocking the central part of the house. The shaped trees have a smaller canopy.

I'd also have the arborist look at the other small flowering tree on the left side of the house. It may be planted too close to the house.

The house has such interesting architectural details that I would not paint the trim the same color as the body. If you dislike sharp contrast then paint the trim a few shades darker than the body. That used to be a common custom.

I'd replace the front roman style awning with an awning more suited to the house.

If the awnings in back are useful I would keep them and not worry about the green.

If you determine the juliet balcony thing above the entrance is original then keep it in storage if you take it down. You might want to put it back later.

If you are not an avid gardener you might add a low uniform ground cover in the bed in front of the tree.

I love everything about the house (except the snow!). The color scheme detracts from the house. You can go all different directions- I favor an arts and crafts take with some variant of dark olive green on the shingles, chocolate brown on the trim, black sashes, purple door. I support your instinct to remove the silly Juliet balcony- clearly tacked on. The crab apple is lovely, I think it could be opened up significantly so it was more transparent.

A lot of crabapples tend to put up watersprouts if pruned. Those are thin branches growing straight up from structural branches. They are usually pruned out, but it becomes an ongoing battle with the tree. Many year ago, we had a crabapple that lost a major branch to a Philly ice storm. For the two more years we lived in that house, it was us versus the tree. It is hard to tell from the pictures, but that may be an issue with this tree. Don't have it sheared, but thinned

I assume you have seen the heating bills for the house. What the ice dams say to me is that the house has never had additional insulation put in under the roof. It is going to be a big job to put it in, and until then you will be spending to heat the great outdoors.

I like deco's idea to create a portico with that dormer. You could remove the iron balcony at the same time.

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Wow, so many responses so far. To answer a few questions:

The front of the house faces north, the rear (with all of the awnings facing south.

The awnings that exist today are actually all black. The green awnings must be a slightly older generation of photos. The garage door is black too. Possible the current owners were starting to tweak the color scheme before they moved.

The shingles and trim are all wood. the windows are all steel except for the big window in the front (far right) that we think actually filled in the original one stall garage, which is vinyl or aluminum clad. Since that window is brown, we would be inclined to keep the windows brown and work it into the color scheme.

I made the assumption that the tree in front is a crab apple based on the fruit observed last time we were there, but I could be wrong since it hasn't leafed out yet. I'm pretty sure that the trees out at the street are Bradford pear. Those would definitely stay one way or another.

Not visible in any picture, and kind of swallowed up by landscaping, but the bottom of the chimney is rough stacked limestone with a slate roof in dark green, dark red, and blue-black that may have once been on the entire house. We thought we might use those two elements and the brick as a foundation to construct a better color scheme.

Emmarene, I'm curious what type of awning you would recommend as more appropriate? Other than what is there and a dome shape, I'm not sure what else is possible.

ptreckle, we haven't seen any plaster issues in the house to date except some bubbly paint in the basement (near the center of the house). The plaster in that area at the front of the house has heavy trowling that we are pretty sure is original, so we don't think anything has been patched over either. When these photos had been taken at listing, we had just gotten 1.5' of snow in 2 days. Everyone's house had massive icicles on them like that including our own. But it's something we will definitely be keeping in mind going into the house inspection.