Realty Check

The Hamptons market entered 2026 the way it tends to after a landmark year: tighter, pricier, and entirely unapologetic about both. Inventory fell, records fell faster, and the handful of trophy properties that did come to market were met with the kind of conviction that only arrives when serious buyers have been waiting a very long time. 

What follows is a look at a few listings that tell the story of this moment rather well. One set a new price record for Shelter Island. One spent several seasons on Bravo. One presents an opportunity to own an iconic waterfront restaurant and marina, and one offers something rarer than either: a turnkey home with nothing left to want. Remember, even with record breaking prices, the sunsets are always free!

Owners Sitting Pretty
Regarding your sunsets: we hope you bought a place quite a while ago; today’s buyers are seeing sky high prices and not much in inventory. A banner 2025—complete with a few splashy trophy-property trades—has only made things tighter, because nothing drains supply quite like a great year for sellers who now see zero reason to sell again. Listings dropped 10 percent year-over-year last quarter, marking the second decline in three quarters, and unsurprisingly, fewer homes mean fewer deals. First-quarter sales came in more than 16 percent below the decade average, which is what happens when buyers are eager but there’s almost nothing to buy. At the top end, the situation is even more dramatic: luxury listings fell more than 35 percent, and deals dropped about 30 percent. Turnkey properties—already rare in the best of times—are now treated like mythical creatures: frequently discussed, seldom spotted.

And despite geopolitical tensions and oil prices, prices keep climbing anyway. The share of sales above $5 million hit a record, luxury median prices jumped 30 percent to $13 million, and the overall median rose 18 percent to $2.4 million. So yes, inventory may be scraping the bottom of the barrel, but if you’ve got the cash—perhaps courtesy of those record Wall Street bonuses—the Hamptons remains, as ever, a very nice place to park both your money and yourself. Now let’s take a look at some newsworthy listings. One is a record-breaker, one is a TV star, one is a beloved waterfront restaurant and marina, and one is the ever-elusive turnkey new-build.

A New Shelter Island Record 
If you needed a reminder that the East End real estate market operates on its own logic—somewhere between aspiration, architecture, and absurdity—look no further than Shelter Island’s latest record-breaking sale. A waterfront estate at 4 Dawn Lane, originally designed in 1971 by Norman Jaffe, just traded for a cool $16 million, which is less a number and more a statement. Jaffe, for those who appreciate their homes with a side of architectural pedigree, was responsible for more than 600 projects over his career, many of them across the Hamptons, where his sculptural, modernist style became something of a calling card. Repped by Nick Brown and Lidia Murphy of Sotheby’s International Realty, the house—known as the Osofsky House—comes with a bit of a twist: it was expanded by Jaffe himself about a decade after its original construction, a relative rarity in a portfolio where revisions were not exactly the norm. Set on 1.7 acres with 175 feet of frontage on Gardiner’s Bay, the property blends that signature Jaffe geometry with enough modern upgrades to keep today’s buyers from panicking about things like insulation and Wi-Fi. The result is a six-bedroom, eight bath, two-half-bath compound with 6,700-plus square feet, a guest wing, cantilevered decks, a waterside pool, tennis (with pickleball lines, because it’s 2026), and just enough understated landscaping to suggest that nature and money can, in fact, coexist peacefully.

The sale didn’t just edge past the previous Shelter Island record—it obliterated it, surpassing the 2023 high-water mark by more than $3 million. That prior benchmark, a $13 million trade at 2 Charlie’s Lane, had already seemed ambitious at the time, especially for a market where the median sale price hovers around $1.2 million. 

Looking for a Summer House?
Meanwhile, over in Sag Harbor, a very different kind of property is trying to cash in on a very different kind of fame. The house made famous by Bravo’s Summer House series—yeah, us neither, but just nod along—is back on the market for $5.65 million, offering buyers the rare opportunity to own not just real estate, but several seasons’ worth of televised questionable decisions. Located at 2136 Deerfield Road, the 8,700-square-foot home has served as the backdrop for five seasons of the Bravo series, which follows a rotating cast of attractive people making dubiously wise life choices over long summer weekends. As if the property itself didn’t have enough personality—seven bedrooms, eight-and-a-half baths, a freeform pool, spa, and a pool house practically designed for themed parties—the current buzz is being fueled by off-screen drama involving cast members like Amanda Batula, West Wilson, and Ciara Miller (again, us neither). The details of that situation are messy enough to make the real estate feel almost secondary, though not quite.

To its credit, the house is well-equipped for both entertaining and recovering from entertaining. Built in 2002 and renovated in 2020, it offers a movie theater, a gym, and the kind of indoor-outdoor flow that listing agents love to describe as “seamless.” There’s also a detached garage, a finished lower level, and enough patio space to accommodate a small army of brunch guests. The property sits on 4.3 wooded acres between Sag Harbor and Water Mill, providing a level of privacy that is either appealing or ironic, depending on how much reality television you’ve consumed. Interested? Get on the horn to listing brokers Alfredo Barreto and Vincent Horcasitas at Saunders.

On The Waterfront
The Oakland family has decided it might be time to cash out of paradise, listing the long-running Sundays On The Bay restaurant and marina for a cool $17.9 million. Of course, super-agent  Enzo Morabito, of Douglas Elliman, has the listing. The 2.73-acre spread sits at the eastern end of Dune Road in Hampton Bays, where bay sunsets and ocean proximity do a lot of the sales pitching for you. Included in the deal: a 4,840-square-foot, 118-seat restaurant wrapped in oversized windows, a 77-seat outdoor deck, two full-service bars, and—because this is the Hamptons—plenty of parking for whoever isn’t arriving by water.

And yes, arriving by water is very much the point. The marina basin comes with roughly 35 slips, including deepwater space for boats up to 90 feet, plus direct access to the Atlantic via the inlet and a fuel dock stocked like it’s expecting a flotilla. There’s also a 2,000-square-foot accessory structure currently pulling duty as an icehouse, in case the next owner wants to lean even harder into the dock-to-dinner fantasy. For buyers thinking bigger—or just hedging—the neighboring former Captain Norm’s Restaurant property is also on the market for $6.5 million via Hal Zwick at Compass, offering another 8,160 square feet and potential for additional slips. If you’re going to spend eight figures on a waterfront compound, why not make it a double?

Turnkey? Yes Please!
And now for something completely different: the pristine, newly built, unapologetically turnkey listing that seems designed for buyers who would rather not think too hard about anything beyond where to place their outdoor furniture. At 6 Trails End Road in East Hampton, a 2022-built, 7,500-square-foot home, listed by Kurt Giehl and James K. Peyton at Corcoran, is asking $6 million, offering exactly the kind of polished, move-in-ready experience that continues to dominate buyers’ wish lists. Located in the Hands Creek Farm community on 1.5 acres, the house checks all the expected boxes: double-height entry, open-concept great room, wide-plank white oak floors, and walls of glass that ensure you never forget there’s a pool outside. The kitchen leans heavily into luxury branding, with Sub-Zero appliances and a La Cornue range serving as both functional tools and subtle status symbols. There are marble countertops, custom finishes, and enough design cohesion to reassure even the most commitment-phobic buyer.

Upstairs, the primary suite delivers the usual promises—vaulted ceilings, terrace access, multiple walk-in closets, and a spa-like bath—while the lower level adds a sixth bedroom, a gym, and flexible recreation space that can easily become a home theater or whatever else the next owner decides they need. Eco-conscious features like solar panels and a low-nitrogen septic system nod toward sustainability, though it’s safe to say the primary selling point here is still comfort, convenience, and a distinct lack of renovation headaches. In a market where inventory remains tight and buyers are increasingly selective, homes like this offer a kind of psychological relief: no surprises, no compromises, no waiting.

Ch Ch Changes
Bonny Aarons and Janette Goodstein bring their decades of proven success, unmatched client care, and deep-rooted expertise in the Hamptons luxury market to Sotheby’s International Realty. Known for their integrity, discretion, and results, Bonny and Janette have spent more than 20 years as a powerhouse team—skillfully guiding buyers and sellers through complex transactions with confidence and precision.

Bonny’s distinguished real estate career, combined with Janette’s intuitive, detail-driven approach, has earned them a loyal following and a reputation for delivering exceptional outcomes across the East End. With unparalleled market knowledge and a long history of representing one-of-a-kind properties, they continue to set the standard for elevated service and luxury representation in the Hamptons.