Luxury Market Insider: Regattas, Refinement, and Real Estate on Nantucket

“Nantucket! Take out your map and look at it. See what a real corner of the world it occupies,” exclaimed Herman Melville in his epic novel Moby-Dick. Barely 50 square miles in area and only accessible by air and sea, real estate on Nantucket strikes a perfect balance of quaint and understated meets exclusive and luxurious. Once the epicenter of our nation’s whaling industry, fine original captains’ houses have been meticulously maintained and elevated into distinguished residences lined by pristine private gardens, cobblestone streets and dramatic shoreline.


While real estate on Nantucket boasts a whopping average sale price over $3.7 million for a single family home (1), it is not unusual to find retired Fortune 500 CEOs mingling with fledgling 20-somethings at a local dive bar after a day of fishing. This unique dichotomy coupled with its magnificent natural beauty are two of many reasons Nantucket ranks among the most coveted communities along the Eastern Seaboard. The Luxury Division sat down with a coterie of top Compass - Nantucket agents to learn more about why the discreet New England destination with a striking lack of pretense is becoming known as, “Billionaires Isle.”


“It’s magical. Every day is Saturday.” 



The island of Nantucket is located 30 miles off the coast of Cape Cod, its population rising from 14 thousand during the off-season all the way to 80 thousand at its annual July-August peak (2). Agent Kevin Caulfield details, “The boats anchored in Nantucket harbor in July and August are impressive. 100- to 200-foot yachts, some too large to fully enter the boat basin and instead moored, with smaller boats bringing its passengers ashore.”  Nantucket airport is among the busiest in New England during these summer months, with fleets of private jets overtaking the tarmac. Direct commercial flights from Boston, New York, DC, and Chicago have increased accessibility, and agent Graeden Ambrose smiles, “The second the boat pulls in or the jet lands and you step onto the island, the stresses of life vanish and everyone is so happy. It’s magical. Every day is Saturday.”



This spirit of repose and relaxation clearly resonates with ultra-high-net-worth buyers, as most Nantucket homeowners enjoy a portfolio of residential properties, spanning markets from Palm Beach Island to trailside Aspen. “These are legacy, generational properties,” explains agent Shelly Tretter Lynch. “Real estate on Nantucket has become a veritable global destination for those seeking privacy, security, and leisure surrounded by nature at its finest.” Agent Allison Mazer adds, “Palm Beach is a particularly strong connection to Nantucket and there are crossover businesses between the two communities, such as Lola Restaurant and The White Elephant Hotel, which enjoy a shared level of service excellence these residents and customers expect.” 


“It’s billionaires in beat up Jeeps.”

The island of Nantucket takes great pride in its personality paradox, simultaneously oozing with exclusivity and its inverse bohemian vibe. Agent Marybeth Gilmartin-Baugher points out, “You do not see flashy cars parading down Nantucket’s Main Street. While our homeowners may live quite differently while residing at other properties in their portfolios, when they're on Nantucket they’re decidedly understated. It’s billionaires in beat up Jeeps.” The restaurants and nightlife perfectly demonstrate this polarity, with food offerings ranging from extreme fine dining to clam bakes and food trucks at Cisco Brewery, plus dive bars like The Chicken Box for an egalitarian evening of live music, ping pong and darts among tycoons and tradespeople.



With 82 miles of prime coastline, the island of Nantucket is an absolute boater’s paradise, and at just 14 miles long and 3.5 miles wide, biking is a fabulous way to relax and explore. Other beloved local pastimes include surfing, golf, tennis, and simply lazing on the beach. Graeden has been a Nantucket resident for nearly 30 years and proudly adds, “80-plus miles of pristine beaches all open and free to the public. It’s a treasure.” The island’s beauty and culture are simply superb, and one can enjoy utter privacy and seclusion, or alternatively be super social at its terrific downtown scene. Shelly shares, “Noteable annual events include the Nantucket Film Festival, Daffodil Festival and Wine Festival. Then there is The Nantucket Project, a sort of brainpowered think tank with Ted talk-like events. For the outdoors person, Nantucket’s fishing and sailing tournaments such as the Figawi Annual Boat Race are legendary.”


Nantucket’s immaculate town center is lined with beautiful shops and restaurants, for which the community has jumped through hoops to maintain the integrity of the island and largely exclude chain stores and restaurants.”Development in general is swinging toward luxury, including high end retailers,” explains Kevin. “Great luxury hotels like The Wauwinet, along with a host of smaller boutique hotels, are being converted into real luxury destinations.” Allison adds, “Nantucket residents are notably community-oriented and philanthropic, with charities widening their reach and impact more and more on the island, including amazing organizations such as the Nantucket Boys and Girls Club, catering to the wellbeing of kids and the Community First Project, through which Navy Seals and Delta Force train Massachusetts first responders to make our communities safer.”



“The entire Nantucket market is essentially luxury.”



 With the emergence of remote work from home, real estate on Nantucket has transitioned from a summer destination to a full-time residence for many homeowners. This, coupled with its inherently finite island geography, has resulted in tight supply and ever-rising prices. “Bear in mind, almost half of the island is now permanently protected to keep the terrain as pure as possible. This is accomplished by requiring two percent of every real estate transaction go to the Land Bank conservation trust,” Kevin reports. “And the buyers keep coming, from as far as Florida, Texas and Colorado, pushing the median selling price for land up over 40% (3). The entire Nantucket market is essentially luxury.”



There are different ultra-luxury residential enclaves on the island, each offering its own unique character and lifestyle. “The charming cobblestone streets and captains’ home are in Brant Point and the Town Center,” describes Marybeth. “Siasconset (locally referred to as Sconset) boasts a Norman Rockwell-esque village and beautiful bluffs overlooking the sea.” Shelly continues, “Monomoy has a magical waterfront setting along a quiet corner of Nantucket Harbor, with proximity to town and the distant sounds from the historic bell tower and ferry horns.”  Graeden adds, “Nantucket’s luxury markets are expanding beyond their traditional boundaries, extending into Dionis -  Madaket, Cisco -  Long Josephs Point, and Surfside. These areas are on an especially sharp luxury trajectory.”


Graeden shares insight on the impact of inventory being at all-time lows. “Finding homes for ultra-high end buyers has become a real challenge, particularly at the $10 million plus price point. Buyers are even making unsolicited offers to homeowners, turning over every possible stone in their quest to secure a piece of real estate on Nantucket.” Kevin underscores, “This is why it’s essential to work with a skilled local agent who knows which trees to shake in this highly competitive and hyperlocal market. Even vacation rentals are being scooped up far in advance and at lightning speed, often in September for the following summer.”



Allison thoughtfully summarizes her feelings about her island home. “It’s hard not to marvel at the ease and happiness that emerges from being on this faraway land. Nantucket is not a day trip but a commitment. This means long stays, and deep and meaningful community building opportunities, from charitable connections, business connections and personal friendships. The residents of Nantucket really come together and make an impact.”

Work With Us

Ken interprets market data, staying in constant communication and offering valuable insight that then translates into an informed decision.

Contact Us