Most owners choose a Nantucket real estate agent on a friend's recommendation, a familiar name or a good first conversation. None of that is wrong, but it isn't an interview. A listing here is a large decision, often made from another state, in a market with few comparable sales and a short season. These questions work with any agent, including me.
"How did you arrive at that number?" matters most. A good answer is a short list of closed sales from LINK, the island's multiple listing service, matched to your house on segment, condition and position, each with its first asking price, its sale price and its time on the market. You should see the evidence, not just the conclusion.
Two answers deserve caution:
The town's assessment. It exists to divide the tax levy among owners, not to track what buyers pay. On Nantucket the two numbers have little to do with each other.
The highest number in the room. A high price isn't a promise. Over the last three years, the 219 single-family houses that sold within 30 days of listing closed at a median 99.4% of their original asking price. The 38 that took more than a year closed at a median 76.7%. A price chosen to win the listing is paid for later, by the owner. The guide to why island houses don't sell has the full figures.
Ask: "Would you take this house to the open market right away, and why?"
Of the 137 home sales LINK recorded from January through August 2026 (houses, condominiums and multi-family), 35 show no marketing period, which is how a private sale enters the record. A quiet round offers privacy and a test of the price, with no days on market accumulating. The cost is that fewer buyers see the house, and you may never learn what the full market would have paid. The selling guide explains how a quiet pre-launch works.
A good answer names both sides, explains the choice for your house, and is specific about how private buyers are reached.
Late spring through midsummer brings the most buyers and the most competing listings. Fall brings fewer showings, from people who came to look. Winter is a small audience with little competition. A good answer ties the date to your house, not to the agent's calendar, and says when the photographs will be taken. For a summer house, that's often months before the listing goes live. The factors behind timing have their own guide.
Ask for the plan in writing. Your buyer will probably see the house first on a phone, from somewhere else. The plan should name:
Then ask who pays for each item, and look at one of the agent's listings on your own phone.
A buyer's attorney will read the town's file on your house, and your agent should read it first. Ask what they'd want in hand before listing. Listen for a current Title 5 inspection if the house is on septic, historic district approvals that match the exterior as it stands, building permits that were opened and closed, and the flood zone. The seller's checklist covers each document, and if something never got a permit, decide what to do before a buyer is involved.
A good sign is an agent who tells you something about your own file that you didn't know.
Ask who opens the door for a showing: the agent you're interviewing, a colleague, an assistant or a lockbox. None is wrong, but that person is doing part of the selling, and you should know who it is.
If you live away, ask who meets the photographer, the septic inspector and the fire department, and how often you'll hear from the agent. A good answer is a schedule: feedback after each showing, and a report even when nothing happened. The guide to selling from off-island lists what an agent should handle for an owner who isn't here.
Commissions are negotiable, and there is no standard rate.
Practice changes that followed the National Association of REALTORS® settlement took effect on August 17, 2024. On the multiple listing services they cover, a listing no longer carries an offer of compensation to the buyer's agent, and buyers sign a written agreement with their own agent before touring homes. A seller can still choose to offer compensation outside the listing service, or a concession toward the buyer's costs. Ask how this works on the island today, and what the agent recommends for your house.
Then ask three plain questions. What is your fee? What does it cover? And what happens if you also represent the buyer?
Massachusetts adds a useful rule. At the first personal meeting to discuss a specific property, a licensee must give you the state's Mandatory Licensee-Consumer Relationship Disclosure, which says whether they are acting as a seller's agent, a buyer's agent or a facilitator. One agent can represent both sides only with the informed written consent of both.
Before you sign, ask:
A good answer is in writing, in plain language, from an agent comfortable with your attorney reading it first.
The state's Division of Occupational Licensure has a free license search on mass.gov, where you can confirm that an agent's license is current. Then ask for the agent's recent listings and the LINK history of each: the first asking price, the sale price and the time on the market. Ask about one that didn't sell, and for two past sellers you can call.
It's fair to ask me everything above. The short version: