The first thing that comes to mind is that you need a path of stepping stones leading up to the door, like you have in the third photo down. I also love the flower filled window boxes and the cottage style flower gardens - both of those would be easy to add to your house, around the foundation and along the path to your door. I notice that your roofline is very flat, compared to your inspiration photos. Maybe you could put a "Story book" roofline just over the door - so remove the square overhang, and replace with a peaked one? Not sure if that would not look right with the rest of the house so square, but it's an idea. You could add a gazebo in the back somewhere. That'd be lovely. I'd definitely plant foundation shrubs along the left side of the house, where there's empty dark space between the bottom of the shingles and the ground. The gap would be better covered up, I think.

I also think I'd try to combine some of the smaller windows into two or so larger ones.

Hnhouser I love your ideas, especially replacing the roof over the door! Genius! I should mention that the main entrance to the house is not pictured, it's in the back. The door you see is technically a "back entrance" in our daylight basement. Love the ideas though.

I don't know about VT, but here in MI, we have to deal with mosquitoes. My aunt and uncle had a place in upstate NY, and there are blackflies and gnats to deal with there too. Plus a LOT of chilly days. You may want to reconsider tearing an enclosure down, and instead turning it into a three season porch type room. My aunt and uncle had one, with a small wall mounted heater. They had wrap around windows and spent a lot of time in there when the weather wasn't so hot, which was often.

Thanks for your comments, mramsey! I grew up on the Maine coast, and my style reflects that...a compromise between the two styles is wise. We would indeed like to upgrade the top southern windows to be more insulated. Cedar shakes are r-7 so that would be an insulation upgrade as well. It might be a bit more complicated, but having a large window there would improve our enjoyment of the home and our view so much. The unheated room was built as a small basketball gym (I'm not kidding) was never finished inside, and now serves no purpose. It blocks our view of our back field and the western sunset over the hills. It's nowhere near the main entrance of our house so it's inconvenient for that kind of storage. I understand the recommendations of a screened porch but my husband has strong feelings about it being easy care, no roof or screens to maintain. I'd like a place to lay in the sun as well, and grow grapes or wisteria on the arbor.

I think pruning the lilacs much much shorter would work well. We definitely need some shrubs in front of the oil tank. The magnolia was planted by my mother in law much too close to the house, and while we have pruned it many times, it still brushes against the siding and blocks our view. The shade is nice in the summer, though. My husband is rooting a long offshoot of this tree in hopes of placing it further away and letting it mature.

I pinkmountain, thank you as well for your comment. Thankfully, we are in the hills where a daily gentle breeze keeps mosquitoes away. We don't consider a screened porch to be an option because of high maintenance and no direct sunshine.

I also love storybook architecture. A neighbour just took a "BC box" (British Columbia, Canada) and added a huge front gable to get a result that looks more charming. $$$

Honestly, I would do the necessary updates to make this house sound and put the rest of your money into your farm. We farm; the more you can do debt-free the better off you'll be. That seems like a self-evident statement but the hard part is letting go of our dreams, especially when we have strong preferences for a dream home. The sacrifice is worth it, I can assure you!

Maybe you can build yourself a sweet little story book garden shed, or add a peaked garden gate. Take cuttings from your lilacs, create a hedge, and hang a gate on the path to your orchard.

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This is hung in a brick wall, much cheaper to use what you have after you prune back those lilacs. In a few years it will be gorgeous!

Thank you Lindsey for your comment :) We have what we need to run our permaculture orchard, and some money to fix up our house. We live debt free and it's very important to us as well. To us, we will be spending the rest of our lives here and want to enjoy our house. We had originally planned to build a curvy cob house before settling here. So, we would like to add some touches to our rectangular and straight edged house to feel more like the vibe we want. I agree about your idea for a lilac hedge, the spot against the road would be perfect!

Can you center the window above the door? I think it would really enhance the entry.

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If you don't have a shop or barn elsewhere, the advice to turn the left wing into one is really wise. I would add a garage door, put in a powder room, and build the shelving and storage you need. Being able to access the bathroom without having to tramp through the house in dirty clothes is invaluable.

My husband is the third generation farmer in his family but I married into it. I wish someone had told me: You will not have time to lay in the sun. You will be filthy most of the time. There will be unexpected expenses every single season. The day doesn't end at dinner time. I know, unsolicited advice sucks but like I said, I wish I knew so I'm telling you :)

One other thing: standing seam roofs are not cheap. I would never consider pulling one apart to create new roof lines in order to suit a different architectural style. Is a cottage look similar to this something you could enjoy? You could do stucco instead of the new cedar shakes, add the peaked portico like someone suggested above, and make the new windows more symmetrical:

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Hi Lindsey, thanks for your ideas about the house! We have an addition out the back of the house with a garage and large shed that meet our needs for storage, tools, etc. We have several farming friends who indeed have many unexpected costs and trials throughout the season, and I agree with your advice for that kind of life! Especially living debt free, too many of our friends have not been able to do that. However, our main source of income is not from the land and we don't consider ourselves to be farmers. I say this with much respect to farming families, and for means of clarifying the needs of our house.

As for the standing seam roof, yes it was indeed costly but worth it to us. We only covered the house on the right side and middle, not the roof of the section we plan to dismantle. I know most of the commenters have advised against taking that part of the building down (including my FIL who built it) but we really are set on it. It's not of highest priority, it will be some years before we get to it

Yes, the peaked portico is my favorite suggestion so far! As well as spacing the windows more symmetrically. I also think a window box below the farthest right window with trailing vines would be lovely. That room is our bedroom and we look out the window often.

er612 thank you for your photoshop efforts! It's very interesting to see what the house would look like with different windows. I think an arched window would add more of the feel we're looking for, though (less modern). The window you placed above the door would likely not work with the idea of a peaked portico. I like simplifying with fewer and larger windows, like you did.

Doubtful that any carpenter/contractor will take on and satisfy all the types of 'nit-picking' rehabs desired by this poster without a solid architectural plan in hand which complies with local building codes. Yankee ways are thrifty. But, in this situation consultation with an architect may save dollars and present to the owners thoughtful ideas to achieve their goal.

@nandina ??

@nuiwida I'm glad my unsolicited advice didn't offend you :) I can't wait to see how you transform your house!

@nandina I'm not sure how you consider this to be "nit-picking". Our siding is rotting, so we plan to replace it. Our windows are damaged, so we'd like to replace them. I've asked if people have ideas about using this opportunity of change to style the house in small/medium ways (like the peaked portico, or landscaping, or a door color) as well as the idea of a bigger window (that's a larger change, but hardly "nit-picking"). I agree that a solid architectural plan would be necessary for window changes and a peaked portico, but I'm not on Houzz for that. I'm here to collaborate on ideas, that is all. Like many others here, I find it enjoyable to dream, and hope to put a few of the dreams into practice.

For future commenters: no need to think of anything wild or grand! I think at this point I'd mostly like some simple landscaping tips, or advice on the practicality of a second story window box.

Does the photo show the front entrance or the back? Owners who use the family entrance may want to spiff up that entrance with landscaping, lighting, and a good walkway from where the cars are.

A big round window can be stunning with the right interior setting and a great view. They cost a mint. Sometimes they become the centerpiece of the house. In your climate, floor to ceiling curtains would keep the room warmer at night, but remember where the baseboard heating would go, if you have that kind.