Have you considered selling this one and buying one that has the features/layout you want? The kind of changes you're describing are likely to cost more than the value of the house...

Thank you for the response. We originally bought this house to live in while building another one because we couldn't find a rental, but it has a beautiful view of the Missouri River and we fell in love with the location and want to stay. It is in a quiet neighborhood and close to everything, so we really want to stay as long as it's in our budget to do so. We haven't done renovation before but have contracted two of our previous homes and enjoyed that . We were hoping to do some of the demolition ourselves and subcontract parts we can't do. Does that still seem crazy? The house is 1350 square feet. I'm attaching pictures of the house and view. We are obviously going to have to take the big trees down, but the roots are also pushing up the concrete and we fear they will hurt the foundation. The one behind the house is within a few feet of the house now with a huge trunk!

I'm not a pro, and I can still say that you aren't crazy to change your house so you can enjoy living there. That's what architects are for... so to banter about, take a look at this staircase, which could be to left of your front door. And however increasing the view works, well here's just one 'wall of windows'-

https://ecomindedsolutions.com/blog/adding-a-second-story/

I have a similar wish to build a second story room or two- possibly you'd have much of it if an entire new structure were built in the space between house and garage - what does it measure?

Can't find exact of course - something like this house.

Bungalow entries don't have high ceilings, so maybe right half of house could stay as is. Rooms on that side that often are regular height: office/ den/ bedroom.... ?

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Again, bungalow type doesn't need a 2-story fireplace/ instead of adding on top of h ouse, what about cozy area like this, view out the back -

and somewhere vault the ceiling [near the new in between section]?

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Expensive ideas, yeh.

If need be, how about 1 1/2 story that's designed well for bedroom? rectangular and sticking out into the back yard....

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You have purchased a beautiful lot. I can't imagine it wouldn't be cheaper and easier to tear down what is there and build from the ground up. Maybe you can reuse the foundation. I have seen that done before. But unless it's in perfect shape, don't do that either. Some foundations from that era will not be acceptable to be rebuilt on.

If you want to do some DIY, save that for finishing work. You can certainly do your own painting and if you know how to do something else related to the finishing like the trim work, you could do that. A bulldozer will remove the house in a day.

Talk to contractors. Usually, you can get a general estimate. That said, you would be wise to consider tearing it down and rebuilding --- at least price out the option. You'll get exactly what you want, you won't be hampered by the parameters/problems of your existing house.

Small homes were often cheaply built and if yours was, problems will dog a substantial gut rehab. It's worth noting that raising the roof means rebuilding the walls. It will probably mean building a new roof. That leaves the foundation. If the foundation isn't up to the weight of what you want to do, you will have built a new building, while stuck with design decisions made by the builder of the old house that might not be what you'd choose for the new.

There is nothing MCM about the front of that house, regardless of when it was built. Consider it a tear down and put up what you want from the ground up. It's a lovely lot.

That’s a teardown. Far cheaper to do that than your plans. Might as well build that new house that you had planned to build. As long as you have the 600-1M in cash. Financing for homeowner involvement on a property that already has a residence on it is gonna be virtually non existent.

Thank you all for your advice! We were thinking we would tear down the garage and the left side of the house and extend it that way with a two story. The full basement was well made with thick concrete walls, but we were planning to have all the electrical and plumbing updated. My only hesitation in tearing down the walls was that it is brick. But we planned to move and resize most of the windows and doors, so that would mean labor to replace or rework bring in all those areas. So it sounds like maybe we will be tearing down the house! I do appreciate all of your help. We have some interesting 1950's metal kitchen cabinets and a Globe Electropanel that looks like it was for a cook top. Is there a site where these might be sold to someone who is looking for retro items?

How is the woodwork?

Try retrorenovation forums or their facebook group for offloading items.

Habitat for Humanity sponsores stores with the hard-to-research name "Restore" that take various home fixtures (including cabinets) for resale. Something unusual would do better on eBay, if you have the time/stomach for that...

Sounds like you all want a new house that has nothing to do with your current one save the location. Can you rent for a year or so while you tear down and build the house you want?