Legal Question in Real Estate Law in Maine

Re: second home sale

It is possible to convert a second home into a primary home then sell to claim the homestead exemption, but that can take years.

If you want an income stream, you could finance the sale yourself and the payments would have a portion attributable to capital gains, but at least you would not have the entire tax due at once.

It is also possible to take the proceeds from the sale and use them to invest in another income-producing property and defer capital gains. This is known as a 1031 Exchange. There are a lot of specific rules to follow, but it another option.