Maybe I am misunderstanding which part of the roof you're referring to as offset, so forgive me if this is an off-the-mark too simplistic explanation! I don't think the roof is offset - I think the area to the left side (when facing the front, as shown in your first picture) is the side of a two-story dormer which was added on later, with its right side flush with the front of the house. Since the house is now sheathed in "new" siding, you don't see where the addition starts. The roof is centered over what would be the original section (or at least the section which existed prior to the dormer addition, whether it's actually completely original, or not.) That also explains why there is so much more room to the left side of the front windows than to the right side of the front windows. Noting that the roof overhangs the right side somewhat, and imagining how it would overhang the left side in the same way, if there were no dormer, you can see that without the dormer, the side of the house would be considerably more than a foot in from where it is now... it would be shifted by the depth of the dormer (revealed in another photo.) It all matches up. I grew up in a Victorian-era house in Maine (of a type commonly referred to in New Hampshire as a "New Englander," although I had never heard that term until I moved to NH, so I don't think it is used much outside of New Hampshire. It is a term used broadly to describe many Victorian-era houses with the front door in the gable end.) It had a similar two-story dormer addition. Do you see any evidence of an addition, when you look in the attic? If you follow the roofline back to the back of the house, and look at the rear facade, it is centered over the rear, isn't it? And that side of the house is all in one plane, save for the dormer, correct? I think the appearance of the roof not sitting properly is also heightened by the fact that the photo is a little bit crooked, and the roof has a substantial overhang. EDIT: Yikes, I only looked at the date of the last post, not the date of the original posts... this OP may be long gone. This post was edited by lizzie_nh on Fri, Sep 6, 13 at 8:40

if it were me, I would introduce myself to the neighbors so you can check out their houses. Someone in your neighborhood has to have good taste and those conversations would be invaluable. You would get to hear about what works and what doesn't work. You will be able to hire the designers and contractors who did work that you like. the second thing I would do is figure out which plants thrive and start with a handful, a small, medium and one or two large. again, take note which plants other people have that Thrive and in which exposures they do best in, north south east west. then I would just, live in your house for a while and the ideas will start to come together. One thing at a time or you will get overwhelmed for no reason.

The term "historical" is often more of a sales pitch for an older remodeled home rather than descriptive of its history. You should have any home you're considering buying inspected by a pro working for you and your interests (rather than the bank or realtor). IF you do purchase it, you might consider recreating front portico into a porch, extending that middle forward facing gable (leaving the curved front) and using a shed roof on one or both sides of it to create a wrap around front porch. https://www.homeplans.com/plan/3647-square-feet-3-bedroom-3-50-bathroom-2-garage-sp140938 Also, while it's still small, you might consider moving that tree farther from the house and adding a few more, if possible. You'd need to know where the utilities are buried before digging to add shade or any other purpose, so you will want to know that before you buy as well.

Well to me it looks like an unadorned victorian Also, make sure to follow the Chicago Bungalow Association on email or FB - while you can't sign up to have your house certified, they share loads of helpful info for any vintage home. Super helpful and lots of local resources.