Behind Hedgerow, The New And Exclusive Hamptons Real Estate Firm
Hedgerow Exclusive Properties, a four-year-old brokerage firm specializing in the ultra-luxury Hamptons market, couldn’t have debuted at a more opportune time.
The firm was founded in 2020 by real estate mavens Gary Cooper and Preston Kaye and launched at the height of the COVID-19 pandemic, when wealthy New Yorkers fled the city in search of spacious, open-air homes and plump, forested parcels where they could isolate without worry. It wasn’t uncommon in 2020 that luxury homes would sell via FaceTime for millions over asking. Frantic buyers, at the time, were paying double, or even triple, the price for Hamptons homes. The pandemic exacerbated an already-lucrative market, and Hedgerow Exclusive Properties capitalized on this demand thanks to its founders decades-long careers in aggregating trust from high-end clientele and understanding what the ultra-wealthy buyer wants.
Cooper’s career, in particular, is a masterclass in quiet dominance. Operating independently in the Hamptons for more than two decades, his career has been defined by discretion, innovation, and a pioneering approach to off-market transactions—long before they become the industry standard. When he started as an agent, he quickly understood the reputation of brokers and how people viewed them. Cooper’s resume includes historic transactions that remain legendary in Hamptons real estate. In 2007, he brokered the nation’s first $100 million deal, selling an oceanfront estate in East Hampton to mutual fund manager Ron Baron. Despite these landmark deals, Cooper’s name and image remain elusive online—a deliberate strategy that mirrors his philosophy of confidentiality.
Preston’s entry into the high-end real estate world was equally strategic. With nearly five years at a leading luxury brokerage, he brought a fresh, modern perspective to the table. When he and Cooper connected, their shared vision of reimagining Hamptons real estate took form. While Cooper’s old-school approach emphasized discretion and exclusivity, Preston’s modern, tech-savvy mindset introduced a dynamic, complementary energy. After meeting and building a relationship, Cooper and Preston were likeminded in seeking to create a firm that was synonymous with heritage and luxury but without their names attached. The duo saw a distinct gap in the market for ultra-private clientele, who also want a more discreet approach when buying homes. Hedgerow operates primarily through contacts and connections and employs less than 20 licensed agents.
“A well-known book by Steven Gaines titled “Philistines at the Hedgerow” talks about this underworld of society in the Hamptons, referencing generational wealth and those who lives behind the hedges, so to speak,” Kaye tells Forbes. “As people who specialize in off-market deals and operating our business discreetly, the name Hedgerow was immediately a perfect fit.”
The founders chose the name Hedgerow Exclusive Properties to underscore their focus on premium, hand-selected properties. The firm has a non-traditional strategy. Unlike today’s traditional brokerages, whose headshots, listings, and ads are plastered across social media, Hedgerow’s style stems from a more old-school approach. Similar to the novel, which chronicles the wealthy set who have made the Hamptons a playground for the rich, Hedgerow is cognizant of the balance between the new money and the old guard. Though they specialize in off-market listings, there are many active listings they hold alongside other brokerages.
“We handhold each product,” Cooper says. “We don’t take on hundreds of listings. We take on what we feel fits the brand and the profile with no set monetary amount and will represent everything from $100,000 to $100 million. However, having our off-market inventory certainly separates us. We also facilitate every aspect of the business in-house, including marketing, operations, and administrative support. It’s about full control to ensure the Hedgerow brand is never diluted.”
Hedgerow’s services extend beyond its real estate prowess and instead trickles into offerings that benefit their clients’ unique lifestyle across industries like private aviation, high-end design, private travel, wellness, or even staffing. To this day, their track record is impressive. Still, the firm is inclusive with working with outside brokerages to co-list certain properties.
Past clients include Jason Rabin, Robert Kraft, Michael Rubin, Michael Evans, and John Foley, among others. Since the firm opened its doors in 2020, they’ve recorded more than $700 million in off-market trades, including a waterfront compound that sold in 2022 for over $118 million, the most expensive brokered deal in Hamptons history. The firm’s current inventory is impressive. Listings include a Mecox Bay Compound, listed for just under $100 million, as well as 43 East Dune Lane, owned by Thomas Lee’s estate, which is listed for $95 million alongside the firm’s third partner, Terry Cohen.
