Dana Trotter Marks 2 Years Leading The Agency Hamptons

Dana Trotter, The Agency Hamptons
Dana Trotter of The Agency Hamptons represents this eight-bedroom home at 39 Timber Trail that is asking $11.495 million.

As she celebrates her two-year anniversary this summer as managing partner for The Agency Hamptons, Dana Trotter is thrilled at the success of her new venture.

“I didn’t skip a beat. All my clients and customers followed me over and I had one of my best years ever.” Ranked #3 in the Hamptons in Real Trends, and #1 in Bridgehampton, her results speak for themselves.
Based in Bridgehampton and East Hampton, The Agency Hamptons currently has 23 licensed real estate agents, and focuses on every where from Quogue to Montauk, including Shelter Island.

“The Agency is growing very quickly,” says Trotter. “We were number 87 to sign on. There are now 140 offices in 13 countries.”

Known for its comprehensive social media presence, The Agency is also leading the way with digital marketing, notes Trotter.

“We’re not just a local brand: We’re a global brand,” says Trotter, noting The Agency’s rapid international expansion. “But despite our reach, we’re deeply boutique at heart. That’s our superpower.”

Dana Trotter, The Agency, Hamptons
The Agency closed a $12 million deal for 172 Cranberry Hole Road, an 11,200-square-foot contemporary on seven-plus acres in Amagansett.Courtesy of The Agency

A Global Brand with a Boutique Soul

Despite the impressive breadth of the company’s reach, The Agency has characteristically small, boutique offices.

“We’re not going to be 100 agents with hundreds of listings,” says Trotter. “We really focus a lot of attention on each of our listings. Our tight-knit team gets behind every listing, clients benefit not just from my network, but from the combined reach of every agent in the office. We lift each other up.”

The giant real estate agencies typically operate on a more proprietary basis, with brokers not known to share information with one another.

“We’re an incredibly collaborative office. Not only within our Hamptons offices, but across the whole company,” says Trotter, noting this philosophy extends beyond the East End. “From Aspen to L.A. to Palm Beach, we operate as one connected company,” says Trotter. “That synergy is rare—and powerful.”

The Agency Hamptons represents this stylish shingled transitional with modern flourishes at 280 Division Street in Sag Harbor. The quarter-acre property also has a heated, gunite pool, finished lower level with walkout terrace and a pool cabana.Courtesy of The Agency

Legacy, Drive, and Unmatched Experience

Before coming to The Agency, Trotter spent 27 years at Sotheby’s International Realty, where with $3 billion in sales, she had been ranked one of the top brokers in the nation companywide and in the top 50 of the REAL Trends/Wall Street Journal’s annual rankings.

With her mother in the business and her stepfather a builder/developer, Trotter seemed destined for the real estate business. Still, she credits her success to hard work and dedication.

“I’ve always had a competitive spirit,” Trotter says. “I’ve ridden horses since I was a kid and always loved the competition side of it. I’m an ambitious person by nature, so I think that’s helped me a lot. In this career, you really have to be self-motivated.”

Though many people are licensed to sell real estate, very few are truly successful.

“There’s a stat that 10 percent of the brokers are doing 90 percent of the business and I think that’s very accurate,” Trotter says. “Getting your license is the easy part. Actually getting traction and making money in the business is hard. You have to really put in a lot of time and effort and plant a lot of seeds and work at it.”

That competitive edge, combined with her Sagaponack residency and lifelong local knowledge, gives Trotter a clear advantage. “This business is about relationships,” she says. “Knowing the right architects, builders, attorneys, and town officials makes all the difference.”

Inside the four-bedroom home at 280 Division Street, asking $4.95 million.Courtesy of The Agency

Exceptional Properties, Exceptional Reach

The Agency Hamptons, which represents sales, rentals, and investment and land opportunities, recently closed on 172 Cranberry Hole Road, an 11,200-square-foot contemporary on seven-plus acres in Amagansett North, for $12 million.

“It was just a really stunningly designed and executed new construction and a really special house,” Trotter says.

Another Amagansett North property, that is currently on the market, is 39 Timber Trail, a 10,000-square-foot, eight-bedroom home built by Larry Kane, that’s listing for $11.495 million.

“It’s got an incredible layout with a first-floor primary,” says Trotter. “It’s got two different pools, an incredible outdoor entertaining area, gym, spa, and steam. It’s just a fantastic house just minutes from Amagansett village, which is so sought after now.”

Perched on one of the highest points in Sag Harbor Village, on a generous third of an acre, is a five-bedroom home, a heated, gunite pool and pool house.Courtesy of The Agency

The Agency Hamptons is also listing two new construction properties in Sag Harbor that were both designed by architect Ricardo Romo-Leroux of RRL Architecture & Design: the four-bedroom 280 Division Street, asking $4.95 million and 8 Jesse Halsey Lane, which also has four bedrooms, asking $4.5 million.

Also for sale in Sag Harbor is 11 Carver Street, a 4,500-square-foot, 5-bedroom home, with a garage and finished lower level with gym and media room, asking $4.95 million.

“All three of those houses are really special. They’re real gems, right in the village,” Trotter says.

The newly built house at 8 Jesse Halsey Lane in Sag Harbor was designed by Ricardo Romo-Leroux of RRL Architecture & Design.Courtesy of The Agency

A Steady Market

After a slow start to 2024, the market is gaining momentum. “The weather didn’t help, but in the past few weeks we’ve seen a real uptick in activity, lots of offers, renewed energy,” Trotter says.

The Agency Hamptons also works closely with developers like Green Barn Properties on new builds, with several projects underway.

“In the Hamptons, even end-users are thinking like investors,” Trotter adds. “It’s a limited market with enduring value. When you buy out here, you’re buying into long-term equity.” Calling the Hamptons, “a tried and true market, Trotter predicts that the area will continue to attract buyers, including people who live in L.A., Miami and Palm Beach who will want a Hamptons summer home.

Looking ahead, Trotter sees continued growth—but with intention. “We’re not in a rush to scale,” she says. “We’re building something lasting. We’ll stay boutique, and we’ll stay selective. Every agent we bring on must share our collaborative ethos and commitment to excellence.”

The Agency Hamptons is located at 2462 Main Street, Unit #1, Bridgehampton and 55 Main Street, Unit #4, East Hampton. For more information, call 631-899-3224 or visit: www.theagencyhamptons.com.