The location sounds fab. It looks very welcoming and warm.

Before you start remodeling-get some advice from builders etc...since you don't like the house, and find there no character to preserve-it might be cheaper to build a new one on the same lot.

We did like our new place, and its vibe, so we remodeled..but to build new is easier in many cases.

How much will this house be worth when fixed up?

What is the inside like?

The house needs new siding, proper front entry, roof, gutters, and windows. And more windows added along the sides rather than the little port holes existing now.

You'd be looking at ~$50K to make the exterior pleasing. And who knows how much more to get the inside of to a decent level of nice

How good of deal is this place?

Looks like vinyl siding on there now. Looks like the house was slapped together. Unless the price is amazing, and it's a good location...

A bit of the interior above

Floorplan:

My reason for asking the fixed-up price was not to know your potential gain, but to know the price range of house it will be. My recommendations on siding would be different for a $150K house than for a $1M house.

From your inside photos, it looks to be closer to the former than the latter. It's tidy, but not fancy, so a brick or stone exterior wouldn't be "expected." I'd probably go with vinyl siding. It's a feasible DIY project. For color, consider yellow (cheery) or gray (goes with anything).

The windows are wider than they are tall, and I'm assuming you don't want to alter the structure to make them larger. So I'd go with casement windows, no grids so the view is unobstructed.

Can you post a sketch of the whole floorplan? That would help with recommending what to do about the multiple hobbit hole entrances.

Since you envision flipping this in a few years, I think you need to go out and canvass open houses in the neighborhood for the price range you envision your home being in when fixed up. Loiter a little bit and casually ask the people looking what they think to get an idea as to what they expect for that price range. Then make sure you meet but don't exceed that standard. So if they have 4" vinyl, do that. And be harsh in your evaluation of the house - this is a business decision. It's good that you've lived there so you know the condition of the house, but you've also likely gotten used to some of the quirks (like the ugly and oddly placed entrance), and might discount their unnattractiveness to potential buyers.

Also, if you could post a floorplan that would be great - it's hard to understand how the house flows. I agree though that there is a huge upgrade opportunity to the curb appeal of this house which could yield a strong return.

The separate area in the front is a sunroom? What room does the window to the left of that belong to?

Weedyacres- If there's a way to make this house look like a million bucks, I need to know!

A bulldozer might accomplish this!

Yup, that is a tear down if you want a million dollar house. 100K of work on a 150K house never makes any economic sense for someone who wants to flip.

The location is the determinant of whether it can be a million dollar house. Are there houses in the area that have sold for this?

I have seen architects reply to threads on this site which is the type of advice I am hoping for.