When Mark Greenwald’s client went hunting for a Hamptons house late last year, all of the available properties missed the mark.
One home required too many upgrades. Another had low ceilings and lacked natural light. A third checked nearly every box, but it sat a little too far from the heart of Southampton Village. Greenwald, an agent with Saunders & Associates, couldn’t strike Goldilocks — there weren’t any homes that fit just right.
“The inventory just wasn’t there,” Greenwald said. “The house he wanted wasn’t being built.”
So Greenwald got creative. He found a parcel of land in a location that was much closer to his client’s vision. It didn’t come with the move-in-ready home at the top of his wish list, but it was, at least, a possibility.
He pitched his clients on a new plan: Buy the land, build the dream house and rent for just one more summer. To make the case, Greenwald came armed with suggestions for a builder and architect he knew could get the job done. He told his client it wouldn’t be like starting from scratch. He could use the home that checked nearly every box (except for its location) as a blueprint.
The client took some convincing, but eventually, he committed to the deal. From there, it was just 60 days until closing. Now, Greenwald says, his client is already fielding offers from others who want to buy the home once he’s done with construction.
Greenwald’s maneuvering was part of a playbook that’s becoming more common as buyers and their brokers contend with shrinking inventory in the Hamptons, where listings have been slow to recover from the pandemic-era buying frenzy.
Those constraints only grew tighter last quarter, after a banner 2025 wiped out much of the available stock and further shrank listings. Although a handful of eye-popping deals have already hit the books this year, some top brokers are expecting a quieter summer of sales, in part, because there’s not much else to buy.
But in the Hamptons, low inventory is a feature of the market, not a bug. That’s especially true at its highest end, where superprime properties are scarce to begin with and where even fewer of them trade each year.
The off-market hunt
By Bespoke’s Cody Vichinsky’s estimation, only a few hundred oceanfront estates exist across the South Fork’s hamlets, and many of them have traded within the past two decades. It’s part of the region’s perpetual cycle: Wealthy buyers scoop up aging homes in coveted locations, then tear down what once passed for ultra-luxury to build their own megamansions.
Although inventory appears to have reached an acute low point, the full picture of the most desirable inventory is hard to pin down, as so many of the biggest deals never officially hit the market to begin with.
In the discreet and cash-flush hamlets of the Hamptons, owners of the most coveted homes often entertain name-your-price offers privately. That means that publicly available marketplaces, where inventory data is collected, typically miss listings for homes that will turn out to be among the market’s most significant sales.
Some say that dynamic has rendered brokers more necessary. When inventory is hard to come by, those who can source homes hold the keys — literally and figuratively.
“The inventory story is bullshit. What I see is a consistent marketplace. I see a lot of brokers who came into the business and should leave.”
“That’s been my forte, to find things that aren’t on the market officially,” said Douglas Elliman’s Paul Brennan. “Something is always for sale given the right price point.”
That philosophy was behind one of Brennan’s latest blockbuster deals, the $57 million sale of an oceanfront estate in Bridgehampton. Brennan had sold the home at 125 Mid Ocean Drive to Shutterstock Co-founder Jon Oringer roughly a decade ago, just a couple of years after Oringer took the photography platform public.
Last year, Oringer called Brennan and said he was thinking about selling. He’d tried to offload the property in 2021 for $52 million, but a deal didn’t materialize. Now, he told Brennan, he was open to shopping it again.
“I called a couple of people I knew, brokers who work in that area, and we found the person,” Brennan said. The deal closed in October, with Brennan and two other top Elliman agents, Erica Grossman and Martha Gundersen, representing Oringer. Compass’ Terry Cohen brought the buyer.
If one of those trophy properties does hit the market, it’s often because the owners’ desired price is aspirational. Sometimes those sellers want to signal they have the “Fabergé egg” of real estate with a splashy headline and price to match.
“Once they come on the market officially, usually the prices are too high,” Brennan said. “They sit for a year or so before they sell. You run the risk of that happening, and there’s only a certain amount of people who can afford to do that.”
Competition on the waterfront
Along with tight inventory, the feeling of a tight squeeze could be chalked up to a larger population of brokers who flocked to the market in busier times.
Ed Bruehl, the managing director of Christie’s International Real Estate Group’s office in East Hampton, said that the new arrivals came in response to the pandemic-era market, when closing deals was like “shooting fish in a barrel.” That’s no longer true, said Bruehl, who is himself tasked with staffing Christie’s outpost in the region, which opened up on the heels of the pandemic-fueled boom.
“The inventory story is bullshit,” said Bruehl. “What I see is a consistent marketplace. I see a lot of brokers who came into the business and should leave.”
The additions increased competition for listings across the balance of the market, Bruehl said, along with attorney-to-attorney trades.
He added that several trades happened last year after one owner got in touch with the owner next door and had their lawyers broker a deal for the adjacent property without listings ever hitting the market. He also pointed to Compass’ private exclusive database as also likely chipping away at the numbers.
However, that restriction is less prevalent at the top of the market, where the same few leading agents continue to handle the bulk of the business. The lifeblood of Hamptons real estate, the bankers and private equity moguls who buy homes both as investment assets and social class symbols, is still moving.
“Goldman Sachs will always buy south of the highway. They don’t care about price,” Bruehl said. “The aces will call the top producers and say, ‘Show me what I can buy.’”
“The inventory never shows,” he added.
