Maine

While you might get some helpful insight here, your best source of information is going to be your lawyer (or preferably practicing lawyers in both states). Building and zoning regulations can vary a lot even between towns within the same state and getting a lawyer who is familiar with those regulations will help you narrow in on a location that fits what you need.

The most you can really get from Reddit will be a general idea of "X state has less regulations than Y". That might be helpful for you, but certainly should be taken with a grain of salt and backed up with more reliable information sources.

Maine was made for precisely this. I grew up on a piece of land that contained 8 homes, a central meeting hall and central dining hall, and I was raised in a multigenerational 'commune,' four generations at one time. Family compounds seem very commonplace there.

Thank you 🙏

Thank you 🙏

I’m a Vermonter, landowner and zoning board member. I’d say your vision would be challenging to execute in vt because zoning generally limits the number of dwellings that can exist on a property without subdividing. It’s easy to have a primary dwelling and an accessory dwelling or a duplex, but beyond that it gets sticky unless you’re going to incorporate as a nonprofit. Beyond 2 dwellings you basically are treated as a developer rather than a homeowner. You can of course own multiple plots of land but that gets expensive tax wise since most of your property tax will be based on the 2 acre homestead site. I’ve seen this as a challenge for people trying to build intentional communities. Zoning varies by town so if you’ve got your eye on a parcel you’ll really want to get to know the local ordinance and the development review process in the town and consult with a knowledgeable land use attorney first. It’s a shame in my opinion since multigenerational homes/compounds were pretty much the standard for most of our history here.

So even if the other buildings would be considered "outbuildings" without their own addresses, that would be hard to pull off?

Outbuildings are easy there aren’t really limits for barns and sheds, it hinges on whether they are considered “dwellings” which can be pretty vague and varies by town. If it has a bathroom and a kitchen it’s probably a dwelling. Some towns have provisions for seasonal dwellings etc.

Vermont is addressing the many zoning laws that will make this difficult right now. Some towns are loosening up their restrictions. Maybe find the town that won't restrict you and start from there. People certainly do this, I know someone doing in E. Montpelier right now.

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You might just buy a larger piece of land and subdivide it to make this more straight forward.

In my town I could essentially have 2 houses on our lot ( dwelling and accessory dwelling) The limit was the septic capacity which is done by bedrooms here in vermont.

If you wanted say 3 homes you’d need to subdivide. Again this is my town.

Even if they're off grid simple tiny/small homes or cabins? Just clarifying.

Try the NE corner of VT. Some nice towns with relatively affordable land and little / no zoning.

It usually depends on whether they have plumbing or not. No plumbing is more of a seasonal camp I think.