I have a place on Cow. You will need to either rent or purchase a slip. You can tow your boat every weekend. That gets old quickly. There are no roads on any island, except the bridged islands, so there is no need for a car. Tuftonboro has a town parking lot for guests. It does require a parking pass. Most slips come with one or two parking spots. There are barges for hire to get large items to the islands. Everything is carry in, carry out. It is a total different lifestyle compared to living on the mainland. As mentioned, it is best to start with an island realtor. They are the experts on island living.
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