For better and for worse, the look and feel of Nantucket has been shaped by influential developers, beginning with Walter Beinecke who purchased 80 percent of the properties downtown as well as the dilapidated docks in the 1960s and proceeded to mold Nantucket as we know it today. In more recent decades, Steve Karp of New England Development took over many of Beinecke’s former properties and has made his mark through scores of high-end retail and hotel properties dotting the island. But now there appears to be new kids on the block who are wasting no time putting their stakes in the ground.

With breathtaking speed, Blue Flag Partners has acquired a shocking amount of prime, historic commercial real estate on Nantucket. The Boston-based development firm arrived quietly on the scene in 2015, taking center stage four years later when it purchased The Roberts Collection on Centre Street for $25.1 million. The following year, Blue Flag picked up speed, developing the Cannonbury Lane and Hawthorne Park subdivisions, opening a hotel on Cliff Road called Life House Nantucket (formerly Century House), and then acquiring Hawthorn House on Chestnut Street, followed by the Star of the Sea youth hostel, which it wrested from the Egan Maritime Institute for $3.55 million.

This winter, Blue Flag went on to absorb The Beachside for $38 million, along with a $13.3 million historic hospitality cluster that includes The Woodbox Inn at 27-29 Fair (a 300-yearold building that had been condemned by the Nantucket Health Department as unfit for human habitation), 31 India Street and the Pineapple Inn at 10 Hussey Street. The group also acquired The Boarding House and The Pearl from Seth and Angela Raynor for $7.2 million last September.

“The truth is that many of the long-standing owners of Nantucket real estate are retiring after many years of serving the community,” says Brad Guidi, a managing partner at Blue Flag. “As this generational shift is happening on Nantucket, many of these properties need a reinvestment or they will simply not be able to support themselves anymore, financially or physically. Blue Flag is trying to find the balance between all of this while trying to preserve these experiences so the next generation can be able to enjoy what the previous ones did.”

When the Meeting House on Centre Street was shuttered in all of its dilapidated, lopsided splendor, Nantucket lost a rare, unpretentious downtown public space where folks of all walks of life could enjoy plein-air dining along the sidewalk or wander back through the shops to purchase gifts from local artisans. In its place has sprung up the Sister Ship—a chic, neo-Colonial affair enclosed by double walls of privet and ivy with an interior that evokes late nineteenth-century Singapore.

What does all this mean for Nantucket’s economy and downtown cultural life? Comparisons to the Karp empire are inevitable, but—according to Blue Flag’s supporters and principal partners—not necessarily correct. Guidi wants it made clear that Blue Flag does not share the viewpoint that Karp—also known for buying and “poshing up” old hotels—has either homogenized or monopolized any aspect of Nantucket’s economy. “Walter Beinecke’s Sherburne Associates compiled a massive hundred- plus-building commercial portfolio that Steve Karp’s White Elephant Resorts acquired mostly intact and manages effectively to this day,” Guidi says. “By some estimates, that portfolio includes 80 percent of the retail space in downtown Nantucket. Blue Flag does not aspire to be White Elephant Resorts and anyone who suggests this is simply misinformed.”

Blue Flag’s self-described mission to be “stewards of profound experiences” does include high-risk endeavors, including “cleaning up an illegal junk yard into All images from Blue Flag’s Faraway Nantucket hotel a cluster subdivision” and running Sister Ship at a loss “so that the islanders would be able to enjoy a night out when everything else is closed.” According to Guidi, Blue Flag has and “will continue to put the Nantucket community first in every decision we make.” To that effect, Blue Flag has shown commitment to supporting the local economy. “One hundred percent of the hotel and restaurant management lives year round on the island,” he says. “In fact, we value our staff so much that we personally cover housing for them.”

Terry Sanford, also a managing partner at Blue Flag, was born in the Cottage Hospital and attended public school on Nantucket. “As a native of Nantucket, I am acutely aware of how important each of the properties we become stewards to are to Nantucket’s culture,” he says. “We do our best to carry on the legacy and bring it into its next iteration while always respecting the history.”

Sanford makes a powerful testimony to the need for firms like his to take on projects like The Woodbox, a “neighborhood gem” that “languished on the market for over a year without interest from a single conservation group nor a well-heeled neighbor.” Noting how many boutique inns and smaller commercial properties are now being converted into single-family homes, Sanford claims that in order to preserve The Woodbox as a restaurant, “Blue Flag stepped in when we perceived that residential conversion was imminent.” He adds, “Despite having existed for more than hundred years, these ‘powers that be’ argue that any commercial use is inappropriate in this now ritzy residential neighborhood.”

While it may not be advisable to hold one’s breath in anticipation of the return of the famed Woodbox popover, rest assured, The Pearl and The Boarding House will be open for business this summer. “Seth and Angela founded The Pearl thirty years ago and truly created magic on the island,” Guidi says. “We are honored that they have entrusted us to be stewarding their decades-long legacies, even down to some of the recipes that have made them island favorites. Guests can be assured that these menu favorites will continue to be front and center and new dishes will be introduced as well in the updated spaces.”

Of all of Blue Flag’s acquisitions, perhaps the most uniquely beloved is The Star of the Sea. Built in 1873 as Nantucket’s first lifesaving station, it had been run for the past sixty years as the island’s only youth hostel. A forty-bed open-floor operation sporting Victorian-style architecture where college kids, middle-class families and the thrifty globe-trotter could stay for less than $50 per night, The Star of the Sea was the only real budget lodging on Nantucket.

Sanford agrees that The Star of the Sea is irreplaceable. “It’s a special property whose hostel-style hotel business model ultimately failed and could no longer support the capital needs of maintaining the buildings,” he says. “When it was put up for sale, there were proposals to convert it to residential use or to turn it into a museum with corporate offices. Our team at Blue Flag was compelled to try and salvage the only hotel experience on the South Shore.” The viability of maintaining this property for lodging use is up against the complex and sometimes crushing regulatory oversight of the town. “But the opportunity for an island visitor to spend the night under the stars,” Sanford says, “listening to the surf endlessly roll in is an endangered Nantucket experience and one worth trying to save and protect.

”When asked what their long-term vision is for their growing portfolio of properties, whether to hold or eventually sell, Sanford says, “We look forward to continuing to honor the history of the island we know and love with our thoughtful approach to design and locally- rooted experiences.

”In an era seemingly defined by divisiveness, Blue Flag is reaching across the aisle to neighbors who suspect their motives are strictly profit-driven. “We have found that trying to protect Nantucket’s cultural experience is one thing, agreeing to what Nantucket’s cultural experience is, is quite another,” Sanford says. “We’re doing our best to find that balance…time will tell where this ultimately lands but we will do our best to preserve Nantucket as we know and love it.”