I’m a little confused- do you mean you are hoping to stay stationary in a tiny house for a while or stationary in an apartment for a while, then getting a tiny home trailer?

Tiny homes on wheels versus on permanent foundations, you’re probably aware, are treated pretty differently by towns zoning wise. On wheels will be the hardest. CT isn’t the most liberal. On permanent foundations, there are many towns that allow it and many that don’t. The zoning atlas link can help you identify those.

Of course, getting permission to park longterm from someone who has a house on the same property is something you could do either legally or get away with indefinitely, especially in places with privacy or more rural.

I don’t know which towns or sections of towns would allow wheeled indefinitely on your own piece of land, where there is no existing house. There might be some in the state.