After a Summer of Hamptons Hotel Openings, the North Fork Gets Its Own: Oyster Estate in Greenport

The Greenporter has a new name and a far more confident point of view. Blue Flag Capital opened Oyster Estate in Greenport in early September 2026, transforming the former Greenporter Hotel at 326 Front Street into a 34-room boutique retreat in the heart of the village, steps from the North Fork’s working waterfront.

Blue Flag, the Boston-based hospitality investment firm behind Faraway Nantucket and Faraway Martha’s Vineyard, runs the hotel through its in-house management company, Collared Martin Hospitality. Oyster Estate is the group’s third East End opening of 2026, following Hotel Corduroy in Montauk and Faraway Sag Harbor, and its first on the North Fork.

“Oyster Estate represents exactly what we look for at Blue Flag: a property with an established history in a destination that has a very clear identity of its own,” said Jason Brown, co-founder and CEO of Blue Flag Capital. The structure stays; the rooms, baths, public spaces, courtyard, and pool have all been redone.

Photo Credit: Matt Kisiday

Blue Flag designed the interiors with Islyn Studio, drawing on the historic bay houses of the Long Island coast. Wood shapes nearly everything, from framing to built-ins, in tones of clay, weathered green and salt-softened stone. Greenport flowers are dried and pressed into the lobby tiles, and a hay plaster ceiling recalls the salt marshes.

The common spaces unfold as a series of lived-in rooms rather than one lobby, layered with books, found local objects and plants. Guest rooms start at 260 square feet for a Classic King and come with Parachute Home linens and robes, Salt & Stone bath amenities, Tivoli Bluetooth speakers, Fellow tea kettles, and stocked minibars.

Photo Credit: Matt Kisiday

“The bones of the property remain, but nearly every aspect of the guest experience was reimagined, drawing inspiration from Greenport’s maritime heritage and creative spirit to create something that feels distinctly rooted in the North Fork,” said Brad Guidi, co-founder and chief development officer of Blue Flag Capital. The courtyard proves it.

Rebuilt as the hotel’s social heart, the courtyard and pool are made for long afternoons that drift into dinner and cocktails. Fire pits are lit at dusk, complimentary bikes wait for the short ride into the village, and mornings bring complimentary coffee, tea and pastries from local Greenport favorites.

Photo Credit: Matt Kisiday

The final piece is Fortune Favors, the hotel’s cocktail bar, restaurant and listening room, which pairs Asian-inspired dishes expressed through a Greenport lens with a dynamic cocktail program and a dedicated room for vinyl. Blue Flag announced it for later in September, though the hotel’s own site still lists it as coming soon.

Getting there is refreshingly simple. The LIRR’s Greenport station sits at the end of the line, steps from the village, and the Shelter Island ferry leaves from the foot of Main Street. After a summer of South Fork openings, Blue Flag’s quietest property may turn out to be its most persuasive.

For more of Haute Living’s Hamptons hotel coverage, see the best luxury hotels in the Hamptons, from Faraway Sag Harbor to Hotel Corduroy and the luxury Hamptons places still worth the drive after Labor Day.