Realty Check

Hot Sales and Listings…Along with the Latest Real Estate News in the Hamptons and Beyond

Welcome to Fall! It’s the season in the Hamptons when the whole place goes from “endless summer glamour” to “Instagram influencers in cozy sweaters.” The drink du jour is a pumpkin spice latte from charming farm stands charging $40 for a decorative gourd. Restaurants suddenly rebrand their menus as “farm-to-table autumnal harvest experiences,” which is fancy talk for adding truffle oil to butternut squash soup. 

Another One Bites the Dust
Those of us who can remember East Hampton before it became Rodeo Drive have been hard hit by what is almost certainly the soon closure of Sam’s on Newtown Lane. The building recently sold for $6.45 million, with Hal Zwick and Jeffrey Sztorc at Compass representing the buyer and seller.

Sam’s has two years left on the lease, but let’s face it: ain’t no amount of pizza sales is going to be enough for the new rent. Too bad.

Wonder what will move in? Dior Pizza? Cartier Bagels? Stay tuned.

Southampton Farmhouse with Bonus Barn 
If you’ve ever dreamed of rustic charm without the actual rustic part, 645 North Sea Mecox Road in Southampton might be your scene. The so-called farmhouse-style home sits on more than two acres of manicured countryside (read: not a weed in sight) and comes with a 1,500-square-foot barn, original to the property but now transformed into a “versatile studio” — code for “whatever the new owner’s Instagram aesthetic requires.”

Listed with Pat Garrity of The Corcoran Group for a shade under $5 million, the 3,327-square-foot house is bordered on three sides by a 38-acre reserve, offering that elusive “privacy but make it Hamptons” vibe.

The four-bedroom, three-bath home welcomes guests with a 110-square-foot wraparound porch and a living room big enough (17 by 28 feet) to make even the largest Restoration Hardware sectional feel petite. The chef’s kitchen has the usual suspects — Viking, Asko, Sub-Zero — plus two farmhouse sinks. There’s a shiplap-lined dining room, a study, a mudroom, and more rooms than anyone with a cleaning crew should admit to.

Upstairs, the primary suite features a private balcony, walk-in closet, and a sauna. Outside, there’s a 20-by-60 heated gunite pool, bocce court, vegetable garden, bonfire setup, and even a tree house for the kids or the adults who need to escape from weekend guests.

Montauk Minimalism
Designer Esha Soni’s handbags are known for their sculptural simplicity — and her Montauk home, now on the market for $4.35 million, carries the same DNA. Think: serene, sun-drenched, and effortlessly minimalist — the kind of place where even the air feels curated.

Nicole and Zachary Tunick of Douglas Elliman are marketing the 3,400-square-foot home. Set on just under an acre, the four-bedroom, four-bathroom home features cathedral ceilings, walls of glass, and design choices so tasteful they might make you rethink your own furniture.

The kitchen — with its Wolf range, wine cooler, and oversized pantry — flows into a living space built for entertaining. Downstairs, a walkout level holds two more bedrooms and a lounge that practically demands a linen throw and a moody playlist.

Perched high above Fort Pond Bay, the home offers 180-degree water views and a massive deck with a retractable canopy. Privacy comes built in and it’s within Uber distance of the Montauket. Fab.

Shelter Island Sells Big 
A Shelter Island home just missed breaking the island’s real estate record, closing at a mere $12.85 million. Tragic, really. Still, it’s one of the top sales in Shelter Island history and the biggest of 2025 so far.

The waterfront property at 1 Pandion Road, represented by Terry Cohen (formerly of Hedgerow, now Compass) and Joshua Greenwald of High Line Properties, came in just shy of the $12.95 million record set in 2023. The buyer’s agent, Ben Dixon of Douglas Elliman, diplomatically called the sale “a testament to Shelter Island’s growing recognition,” which is broker-speak for “people are finally realizing how pretty it is over there.”

Set on 3.4 acres overlooking Coecles Harbor, Gardiners Bay, and even the distant Atlantic, the modern 6,000-square-foot home was designed by CTLA Design and David Neff Architecture — with enough glass walls to make curtains feel obsolete. There’s also a saltwater pool, outdoor kitchen, and private deepwater dock perfect for guests to arrive in style.

North Fork Winery Returns to Market 
Osprey’s Dominion, one of the North Fork’s most recognizable wineries, is back on the market — now listed for $6.299 million with Engel & Völkers advisors James and Susan Orioli. The Peconic property spans 50 acres along Route 25 and comes with the whole package: tasting room, production facilities, and even the Osprey’s Dominion brand itself.

Buyers not only get the land and equipment but a loyal wine club base and “certified sustainable harvest” — perfect for anyone hoping to go from sipping rosé to owning the vineyard that makes it. The listing waxes poetic about “rustic charm and refined elegance,” which is shorthand for “yes, it’s pretty enough for weddings.”

The tasting room seats 60, holds 100 for cocktails, and overlooks rolling vines and a pergola bar that practically begs for influencer content. In short, it’s a turn-key lifestyle investment—an invitation to embrace the romance of vineyard living and the prestige of winery ownership.

Home of Beloved Filmmaker Sells
The Sag Harbor home of legendary documentarian D.A. Pennebaker — the man who brought us Don’t Look Back and The War Room — sold within a week for $1.7 million. The charming 1860s house, owned by Pennebaker and his wife, filmmaker Chris Hegedus, for five decades, was listed by Linley Hagen and Kim Kakerbeck of Brown Harris Stevens.

At just 888 square feet, the home is proof that you don’t need size to have soul. Nestled in the heart of Sag Harbor’s historic district, it features period windows, a cross-gabled roof, and a story that practically hums with the ghosts of brilliant dinner conversations. 

Now it’s ready for its next act — hopefully starring someone who appreciates character, history, and the miracle of off-street parking. And we’re going on record: if the new buyer changes that charming kitchen, they’ll have to answer to us.