In the Hamptons’ ultra-luxury market, where timing, trust and relationships often determine the outcome of a deal, few partnerships have proven as effective as that of Douglas Elliman brokers Martha Gundersen and Paul Brennan.
Long-standing brokers on the East End, Gundersen and Brennan formed their strategic alliance about seven years ago, bridging complementary geographic strengths and skill sets. Today, most of their transactions are collaborative.
In 2025, both were recognized among the Hamptons’ top brokers by closed sales – a reflection of their enduring influence in the region’s ultra-luxury market.
Both are perennial recipients of Douglas Elliman’s prestigious Pinnacle Award. In 2025, Gundersen was named the No. 2 Hamptons broker by The Real Deal, while Brennan ranked No. 5 – a testament to both their individual stature and their shared dominance.
Village’s coveted Georgica Estate Section with water views of Georgica Cove.Liz Glasgow
Shared Success, Singular Philosophy
In a market defined by cycles and competition, Brennan and Gundersen remain focused on what lasts: building trust and long-term relationships.
“This is a career for us, not a job,” Brennan says.
“Our success is based on our service, consistency, perseverance and honesty,” Gundersen says – a sentiment that has echoed throughout their careers, which collectively span more than seven decades and exceed $6 billion in closed sales. “Many of our clients have been with us for decades. That continuity is incredibly important at this level.”
Their approach is methodical and proactive. As Gundersen succinctly puts it, “The key to being a good broker is answering every question before it becomes a question.” In practice, that means ensuring that surveys, floor plans, zoning analyses and regulatory considerations are in place well before a property is presented for sale. In the ultra-high-end market – where transactions often involve complex waterfront regulations, historic designations or preservation overlays – this diligence is imperative.
A Complementary Blend of Geography and Temperament
Their partnership is strengthened by a seamless geographic reach. Brennan’s focus has historically extended from Southampton to Wainscott, while Gundersen’s reach runs from Wainscott through Montauk. “Martha became the person I would call when I needed a broker in East Hampton,” Brennan recalls.
Beyond geography, their backgrounds and personalities provide balance. Gundersen’s background in art, combined with her upbringing in a 1700s Massachusetts home, cultivated a refined appreciation for architecture and historic preservation.
Since relocating to Amagansett in the 1980s, she has developed more than 25 years of expertise in Hamptons luxury real estate. Her command of local zoning, architectural heritage and the rhythms of seasonal versus year-round markets allows her to guide clients through transactions that are often as nuanced as they are significant.
Brennan brings a legacy perspective rooted in deep local ties. A veteran of the industry since 1979 and the son of a Bridgehampton potato farmer, he possesses an instinctive understanding of land, open space and value preservation. In 1999, he helped establish the Community Preservation Fund, a transformative initiative funded by a 2.5% transfer tax on real estate transactions. As of 2024, the fund had generated approximately $2 billion to preserve open space and historic properties across the East End. The program has played a pivotal role in preventing overdevelopment and preserving the natural beauty that defines the Hamptons – and draws buyers here in the first place.
“Preservation is what keeps the Hamptons special,” Brennan says. “Scarcity creates value, but stewardship creates longevity.”
“There’s extraordinary biodiversity here,” Gundersen adds. “It’s something we have to protect.” Brennan and Gundersen’s partnership also benefits from stylistic contrast. “Men and women generally talk to people in different ways,” Gundersen observes. “I tend to provide a lot of information, where Paul gets right to the point. I bring more diplomacy and he brings more directness.” In negotiations where timing and tone can mean millions of dollars, this duality becomes a strategic asset.
A Portfolio of Distinction
Their 2025 transactions illustrate that reach.
Among the year’s marquee deals was the $70 million oceanfront sale of 370 & 372 Further Lane in Amagansett, for which they brought the buyer.
The properties – once owned by the late Brian Little of Forstmann Little – feature coveted “road-to- ocean” layouts, a configuration prized in East Hampton’s waterfront hierarchy. Brennan and Gundersen represented the seller in the $57 million oceanfront closing at 125 Midocean Drive in Bridgehampton, a property owned by Shutterstock founder Jonathan Oringer. Brennan had originally sold the residence to Oringer before its completion roughly a decade earlier, underscoring the continuity that defines many of their client relationships.
In Amagansett, they brought the buyers – a California tech family – for 271 Marine Boulevard, which traded for $14.75 million amid multiple accepted offers. In competitive situations such as these, Gundersen notes, success often hinges on “a subtle dance between diplomacy and timing.” Experience enables them to read not only the market, but the psychology of counterparties and sellers – and guide their clients successfully to the closing table.
“In this market, winning a deal is rarely about price alone,” Brennan says. “It’s about timing, preparation and trust.”
Their portfolio consistently includes showpiece estates, landmark homes, and ocean and bayfront properties. Supported by a seasoned team and Douglas Elliman’s global platform, they serve a clientele that increasingly spans continents. Gundersen notes that approximately 15-20% of their 2025 transactions involved parties residing outside the United States, reflecting the Hamptons’ status as a global luxury enclave.
At this echelon of real estate, discretion and integrity are paramount. Brennan and Gundersen’s business is fueled largely by repeat clients and generational referrals. Notably, the buyer in the $70 million transaction was referred by someone Brennan had rented a house to three decades earlier. “If you’re good to people, it comes back to you,” Gundersen says. “If you’re not telling the truth and not ethical, you may win in the short term, but it will eventually impact you.”
For clients managing assets worth tens of millions of dollars, trust is foundational. As Brennan observes, “These are major assets. Clients want to work with people they trust to protect their longterm value.”
Looking Ahead to 2026
Momentum from their banner 2025 has carried into 2026. Several notable properties are already in contract, including 361 Mitchell Lane in Bridgehampton, listed at $11.95 million, and 88 & 86 Louse Point Road in East Hampton, offered at $9.995 million.
Their current listings include two standout East Hampton trophy properties: 64 West End Avenue, positioned on its own cove with sweeping sunset views, offered at $38 million, and 30 Cove Hollow Farm Road, framed by protected reserve land with views of Georgica Pond, listed for $24.995 million.
At the same time, market dynamics continue to evolve. Rising construction costs, longer approval timelines and increasing regulatory complexity have fueled demand for turnkey homes, Gundersen notes. Many buyers today prefer finished, design-forward residences rather than navigating the increasingly complicated process of building from the ground up.
“Buyers today want certainty,” Gundersen says. “A finished product gives them that.”
Global conditions may also shape the year ahead. While it is too early to gauge the broader impact of geopolitical events, international demand has long been a pillar of the Hamptons market. At times of global uncertainty, Brennan says, the East End often emerges as a safe haven for both lifestyle and investment.
“The rentals market is currently very strong, and that typically signifies a strong year for sales,” Brennan says.
Luxury real estate, Brennan notes, tends to move in cycles. “The market is often more psychological than financial. Confidence drives decision-making.” Limited inventory at the high end continues to support long-term value, Gundersen says, particularly as buyer demographics evolve and global wealth migration reshapes second-home markets.
Through it all, Brennan and Gundersen remain focused on the principles that have guided their partnership for years.
“We believe in the long game,” Brennan says. “It’s about relationships, land and legacy.”
For them, the banner year behind them is less a milestone than a reflection of that philosophy – one grounded not only in transactions, but in stewardship.
In a market driven by timing and trust, Brennan and Gundersen continue to play the long game.
PARTNER CONTENT
This article appears as the cover story for the March edition of Behind The Hedges in Dan’s Papers. Tap this link to read the full digital version.
