The closest office to Chesterville is in Westbrook, but contact Home - F.A. Peabody and they may be able to help you.
They have always been very helpful and seem to go above and beyond to help find insurers.
Talking to your Maine neighbors may give you a lead ? Also see if you can get just liability?
I pay a lot for insurance as my fire department's motto seems to be "no small fires." No hydrants for miles. One company suggested digging a pond; I figured the pond, besides being expensive, would bump my liability rates too. Sounds like you're painting the house which sits mostly unoccupied, companies don't like that either. Consider not insuring the barn, although I had a similar barn that went up like a roman candle and the company I had was really easy to deal with. I don't think Agway Insurance is still around, likely some connection there. I think the mindset of companies is that a well maintained, owner occupied place is less of a risk, my new company made me do handrails, chimney caps, and a general tidying up, all of which was reasonable.
For a few years an itinerant barn painter from South Carolina would knock on my door and tell me he would paint my barn for X thousand dollars; I would tell him to go away, and the next year he would knock and come down 20% or so. After a few years we struck a deal. His crew showed up hours later with some big spraying rigs and did a good job in a few hours. No detail work, no prep, just a lot of paint. I had to scrape paint off windows, and I had to paint over trim, but he took a job that would have cost me a lot of time and money, made it look easy. Years later it still looks good.
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That's backward logic. If he allows legal use and gets to know a few locals they can keep an eye on the place. Otherwise he has an abandoned building ripe for thieves and vandals.
What about Ag insurance for the place in Maine? Are you doing anything with the land, timber, etc, that could creatively be called "Ag"?
Insurance companies don稚 like peeling paint old houses because of the liability of lead paint. If it is painted over and sealed they are happy. One way to lower cost of your existing policy is to look at the replacement value they are putting on the house. Over time on older houses that number can get way higher than the house is worth due to the automatic inflation adjustments. We owned several 100-150 old houses on the farm and occasionally would tell the insurance agent to manually lower the value to a more realistic value to keep the insurance affordable. It has gotten so that there is few insurance companies that will insure older houses.
I'm getting quotes and they have vastly over estimated that part, like probably double what the true cost would be. But they told me they cannot adjust that number - it's system generated based on the data put in. The best they could do is tweak things like finishes and square footage to cause the system to spit out a lower number.
My family home is on Cape Cod, and I use it only in summer (6 mo.).
Cape Cod is considered a hurricane zone, and my all wood house there is 288 years old (built 1730).
When the premium was approaching $5000/yr. I told my local agent I would drop all coverage.
After all: I am 78 years old, could afford to build something else, plus, the 12 acres of land will not burn away.
He said let me try to find something for you.
That "something" turned out to be Lloyds of London.
Five years ago the Lloyds premium was $1600/yr. v/s $5000 elsewhere. For 2019 the Lloyds premium is $2100, but the very limited other options are likely now over $6000.