Almost every long-held island house has something: a deck that grew, an outdoor shower added one spring, a basement finished by a brother-in-law, a garage loft with a bed in it. Owners tend to either forget these or worry about them more than they need to. The useful position is in between. Know exactly what you have, and decide what to do about it before a buyer is involved.
During the inspection period, the buyer's attorney or agent reads the property's file. It isn't a deep investigation. It's a comparison between what's on record and what's standing.
When the listing shows five bedrooms and the septic permit says three, or the photographs show a deck the file has never heard of, the questions start.
The last is the most common and the easiest to fix, and owners usually don't know about it until someone looks.
Many island houses sit closer to a lot line, or cover more of their lot, than today's zoning would allow. That alone isn't a violation. A house that predates the rule is lawful, and it can generally be altered as long as the existing problem isn't made worse.
State law also puts a time limit on zoning enforcement. Work done under a building permit can't be challenged on zoning grounds after six years. A structure built without a permit becomes lawful for zoning purposes once it has stood ten years without a recorded enforcement action.
That protection is narrower than it sounds. It covers zoning: where a structure sits and how much ground it covers. It doesn't make unpermitted wiring safe or inspected, it doesn't supply a missing certificate of occupancy, it doesn't satisfy the historic commission, and it doesn't add bedrooms to a septic permit. A buyer's lender and insurer care about all four.
On a house with a septic system, the permitted bedroom count is the house's legal capacity, whatever the floor plan shows. A listing can't honestly call a house five bedrooms on a three-bedroom system, and a buyer who plans to rent will check, because the town ties rental occupancy to the same number.
If your house has more sleeping rooms than its permit, there are only three honest paths: upgrade the system, connect to town sewer if it's available, or list the house at its permitted count and describe the extra rooms as what they are.
You can do the buyer's homework before the buyer does. It takes an afternoon and a few requests.
What you end up with is a short list, usually shorter than you feared, sorted into things to fix, things to explain, and things that were fine all along.
Fix it first when the fix is simple. An open permit that needs a final inspection, a deck that needs a permit it would easily get, a fence or a window the commission would approve: these cost little next to what they cost in a negotiation. A problem found by the buyer is priced at the buyer's estimate, which is usually higher than the real one.
Disclose it and price for it when the fix is large or uncertain. An addition that would need zoning relief, a septic upgrade on a tight lot, a structure the commission might not approve as built. Here the better course is usually to get a clear written picture of what it would take, put it in front of buyers at the start, and let the price reflect it. Buyers can work with a known problem. They walk away from surprises.
What you're required to tell a buyer is a question for your attorney, and it's worth asking before you list, not after an offer. What's practical is simpler: assume the file will be read, and don't describe the house in a way the file contradicts.
Towns, including this one, can permit work that's already been done. It usually means drawings of what was built, an application, and inspections, and for anything covered up, an inspector may ask to see inside a wall or a ceiling. Exterior work also goes to the historic commission, which reviews it as if it were new, and the commission can require changes to what's there.
None of it is quick. If you think you'll sell in the spring, the time to start is the fall before, and the Building Department and the commission's staff are the people to ask about what your particular case will involve.