New York’s brutally long winter didn’t quite freeze the seaside hamlets across Long Island’s East End.
The South Fork notched a standout year in 2025, which brought the region’s first $100 million plus deal in three years. The momentum continued as the calendar turned, with some eight-figure deals crossing the finish line in late fall, while others spilled over into the beginning of 2026.
During the first three months of the year, transactions above $5 million scored a record share of deals in the area, as the median sale price for luxury homes jumped 30 percent to $13 million, according to data from appraiser Jonathan Miller.
The market’s performance intensified at the upper end, with sales of $10 million or more generating $560 million in volume during the first quarter, up from $523 million in the same period in 2020, Bespoke’s Cody Vichinsky told The Real Deal in March.
The stage for a busy start to the year was set at the end of 2025, as a cluster of banner deals closed ahead of Dec. 31. One of the splashiest came in November, when Boston Celtics co-owner Wyc Grousbeck and his wife, Emilia Fazzalari, paid $58 million for an oceanfront mansion in Bridgehampton.
Developer Joe Farrell listed the sprawling modern estate at 165 Surfside Drive for $80 million in 2024. The property spans more than an acre, including an 8,600-square-foot home with eight bedrooms, eight bathrooms and walls of glass facing the Atlantic. It also features a heated pool, a hot tub, a roof deck with an outdoor kitchen and a six-car garage.
Just a month earlier, in October 2025, Shutterstock founder Jonathan Oringer quietly sold his oceanfront home in Bridgehampton for $57 million. The 2-acre property at 125 Mid Ocean Drive, which Oringer bought for $40 million in 2014, is centered on a 10,300-square-foot mansion with eight bedrooms, a gym and a media room. It also has an infinity pool and an outdoor kitchen with a fireplace.
As 2025 turned to 2026, the energy carried over, as deals that didn’t hit the books in time for the new year closed. In January, two adjoining properties in East Hampton totaling more than 7 acres sold together for $30 million.
One of the parcels, at 42 Hither Lane, has a 6,000-square-foot 1930s home, which is known as Holly Hall. It, along with the other, at 55 Middle Lane, found a buyer in October.
Then came the spring blockbuster. In March, Ann Tenenbaum, widow of private equity investor Thomas H. Lee, sold her oceanfront estate in East Hampton for $72 million, marking the Hamptons’ most expensive closing so far this year.
The nearly 4-acre estate has a storied past. Tenenbaum and her late husband bought the property from Lee Radziwill, Jacqueline Kennedy Onassis’ sister, and her husband, film director Herbert Ross, for $16.2 million in 2001. Before that, the land had formed part of an 80-acre compound owned by ink manufacturer Frank Wiborg.
Over the years, Tenenbaum and her husband rebuilt the home twice. When it sold earlier this year, a listing described the property as including an 11,000-square-foot main residence with 10 bedrooms, 12 bathrooms and a heated pool. It also features a 1,500-square-foot guest studio and a tennis court.
Tenenbaum first listed the property in 2024 after Lee’s death the year prior. She initially sought an eye-popping $120 million, but lowered the asking to just under $85 million, where it sat for just under a year before it entered contract.
A month later, another waterfront estate landed in headlines. A Wainscott mansion featured in HBO’s “Succession” traded in an off-market deal for $59 million, and the identities of the buyers and sellers have not been disclosed.
Aviation entrepreneur David Susser and his wife, Marla, built the home at 115 Beach Lane in Wainscott in 2018 and sold it to the latest seller for $45 million in 2021. The 2.5-acre property hit the market two years later with a $55 million asking price, though the listing was later pulled.
The six-bedroom home spans 11,000 square feet and has a gym, screening room and stone fireplace. The property features a deck with an infinity pool and an outdoor kitchen, as well as a four-car garage.
Whether the pace continues through the summer remains an open question, with some brokers already growing skeptical considering the macroeconomic climate. Still, at least one other major deal is on the horizon: a five-bedroom beachfront home at 167 Dune Road, which snagged a signed contract with a $42.5 million asking price.
If the deal closes at that price, it’ll rank among the most expensive so far this year and could signal that more are yet to come.
Summer rentals
Following two sluggish summers, the Hamptons’ rental market appears to be regaining momentum — though the conclusions depend on who you ask.
Getting to the bottom of the market’s performance is a tall order in the luxury enclave, which lacks a centralized database for metrics. Instead, the numbers touted in headlines come from firms tracking short-term rental sites such as Airbnb or brokerages measuring their own rental deals.
Without a hub for the data, some of the clearest signs of the market’s rebound come from a consensus among agents in the area, who say they’ve inked more leases for the fast-approaching summer than they have in recent years.
“Our personal rental numbers are way up from the last two years,” Tyler Whitman, who co-founded an East Hampton franchise of The Agency in 2023, told TRD in March. “We’re churning out four to five rentals a day with only 15 active agents, which is a lot.”
Whitman said that the summer rental market has felt slower over the past two years, as would-be tenants opted to travel abroad and those who previously rented purchased their own vacation pads Out East.
“My feeling was that during prime Covid, people were out here so much that it started to feel less special,” Whitman said. “Now, they’re returning to that typical Hamptons experience.”
However, Serhant’s Kieran Brew pushed back on Whitman’s summation, arguing that leases didn’t decline overall in previous years; rather, renters waited until the last minute to lock down their homes or opted for shorter lease terms.
“No matter how many people went to Europe last year, there were still no empty houses in the Hamptons in August,” Brew said. “Black is always the new black. It never goes out of style.”
He said that the perceived comeback this summer is likely because tenants have been booking earlier, especially after many who waited too long last summer got stuck with “the TJ Maxx of rental houses.”
“They wanted a bargain,” he said. “But when you come out here, you’re not looking for a bargain. You’re looking for beauty.”
Bargains aside, the monthly going rates in the Hamptons appear to be coming back down to earth this summer after a frenzy of pandemic-driven demand drove prices through the roof.
Some of the normalization was caused by more inventory hitting the market, with new construction homes being added to the mix, as well as listings from those who purchased homes over the past few years, according to Keller Williams’ Maria Belen Avellaneda. Overpriced rental offerings also lingered on the market last summer, which likely encouraged some owners to lower their asking rates.
“Tenants have more negotiation capabilities on their side because of that,” Avellaneda said.
