This year marks the 50th anniversary of the Hampton Classic Horse Show— a time when equestrians take center stage (in the ring, that is) in the Hamptons. How have horse culture and equestrian properties influenced the Hamptons real estate market over the years? Are there any trends you are seeing in demand for these types of homes (and barns) today? In addition, is there any special memory you have of the horse show, especially one that might have a tie to real estate?
Sarah Doud
SAUNDERS & ASSOCIATES
BRIDGEHAMPTON
Horse properties across the East End have always been a significant part of the draw to the Hamptons – the rural atmosphere has attracted locals and visitors alike. The open fields and the natural beauty are often what make “the Hamptons” so unique and picturesque – it has helped make our real estate market highly desirable for generations. Some farms and facilities are being preserved as is and others have been and continue to be transformed into world-class luxury equine facilities, trading at high multi-million dollar values. The horse culture remains important to our market. Many old barns are being restored to their glory or repurposed for luxury cars or home amenities. Not everyone chooses to “save the history,” but there are many homeowners, architects and designers who do seek these opportunities and focus on restoring the equestrian influence. Some barns have also been repositioned for commercial uses – a need that is very much in high demand. My grandmother, Diana Brennan, helped secure the land lease when the Hampton Classic first relocated to its current home on Snake Hollow Road. She also helped create the vision for the Boutique Garden — a tremendously smart way to create commerce and excitement on an old farm parcel. My family is especially proud to see the Classic celebrate 50 years. Diana’s great-granddaughters Annabelle and Elizabeth continue the tradition of riding — they had the honor of riding in last year’s Opening Day Lead Line Division.
Chris Ritchey
COMPASS
EAST HAMPTON
Horse culture has left an enduring imprint on the Hamptons real estate market, blending lifestyle, history and beauty. One example is my current listing at 19 Horseshoe Drive in East Hampton, offered at $3 million. The property sits within the Dune Alpin Association, the original site of the Hampton Classic before it moved to its current Bridgehampton location. While the grounds have since been developed into townhouses and freestanding homes, the equestrian heritage remains visible in post-and-rail fencing, wide open pastures, and even a few retired horses grazing in the fields. Across the Hamptons, most notably in Bridgehampton and Sagaponack, but truly everywhere, homes near equestrian properties benefit from expansive sky views, pastoral landscapes, and a unique charm that often enhances neighborhood value. I’ve enjoyed so many memorable Hampton Classic weeks over the years, each special in its own way. A few years back, my table décor of paper flowers with QR codes linking to local charities won “Most Innovative,” which was such a fun honor. But I have a feeling this year will top them all, as I’ll be competing for the very first time. I’m incredibly grateful to my trainer and the horse’s owner, Rebecca Robin, for making this dream a reality.
Dana Trotter
THE AGENCY
BRIDGEHAMPTON
The equestrian lifestyle and the Hamptons have always gone hand in hand. Owning horses has long been considered a luxury, and the Hamptons provide the perfect setting for equestrians to enjoy what they love, whether it’s riding through fields, spending a day at the polo matches, unwinding by the ocean, or boating on the bay. What makes this region so unique is that it offers something for everyone in the family, golf, tennis, sailing, or simply relaxing with a book in a setting that feels both vibrant and serene. The equestrian lifestyle, and the Hampton Classic Horse Show in particular, has long been part of life in the Hamptons, adding to the real estate market by reflecting both the prestige of the sport and the area’s lifestyle appeal. Here, homes are more than residences; they are expressions of a way of life where luxury meets passion. Increasingly, buyers seek lifestyle-driven properties that let them create lasting memories doing what they love. For some, that means a full-scale equestrian estate with world-class facilities; for others, a smaller gentleman’s farm where they can keep their horses close to home. This blend of elegance, sport, and lifestyle continues to make the Hamptons one of the world’s most sought-after destinations.
Susan Hovdesven
DOUGLAS ELLIMAN
SOUTHAMPTON
Horses are a natural part of a farming community and are woven into the history of the area. Local land preservation has allowed for several new barns to be developed that provide beautiful vistas for homeowners who are fortunate enough to purchase a property bordering a horse farm. Buyers will pay a premium for horse farm views. Unfortunately, the current trend is to build as large a home as you can and as many homes as you can overlooking horse properties. This building takes away from the intention of preserving these large open space horse properties. While there are many restrictions on what can be built on a horse farm, the same is not true for what can be built bordering the horse farms. Today, you might see a horse grazing next to a 10,000 sq ft home and that is a shame.” Fellow real estate agents, Marilyn Clark, Raquel Lopez, Rolanda Doolan and Dana Trotter are all as passionate about horses as me. Seeing them at the Classic and under the tent makes me feel a special connection to them. The horse connection is powerful.
Jackie Dunphy
THE CORCORAN GROUP
EAST HAMPTON
I love horses and riding, and I am proud to report that my daughter Daniella is now a riding instructor, so she’s taken the reins as the horsewoman in the family. The 50th anniversary of the Hampton Classic Horse Show is a great reminder of how deeply horse culture is embedded in the identity of our region. It has directly impacted our market — from building design to restructuring the landscape out here. Over the years, we’ve seen farm fields transformed into equestrian centers, and as a result, growing demand for homes near these world-class facilities or close to horse trails. Equestrian properties have long been a cornerstone of our luxury market – not just for their acreage and amenities, but for the lifestyle they represent. In addition, the influence extends to architecture and design, with many new homes embracing a “modern barn” aesthetic that complements the natural beauty of the landscape. The event itself also acts as a catalyst for real estate interest. Many attendees start as seasonal renters and may eventually become local buyers. The show draws international attention, and its prestige elevates the desirability of nearby properties. Maybe more importantly, it introduces new people from around the world to the magic of the Hamptons.
Bonnie Williamson
DANIEL GALE SOTHEBY’S INTERNATIONAL REALTY
HUNTINGTON
I have seen investments in homes close to the Bridgehampton showgrounds and the development of a lot more horse farms that have easy access to the showgrounds. There used to be fields and now there are farms. I have recently sold two properties in the last couple of years to equestrians who want to have their own barns and paddocks on their property rather than keep them at a boarding stable. They don’t want to have to compete with others for ring time and jumps and prefer having their own grooms taking care of their prize show horses and know that they are getting fed the proper food and are being well taken care of. Also, after the initial investment, the board, which keeps going up, is more manageable for those with multiple show horses. I remember seeing all the celebrities with their children or celebrity riders like Peter Boyle, Lawrence Fishburn, Joan London and Kelly Kline. I sat outside a show ring, after competing and negotiated the sale of a $25 million estate on my cell phone to a celebrity while pretending I was in my office.
This article appears in the August 28, 2025, edition of Behind The Hedges in Dan’s Papers. Click here to read the full digital edition. For previous Real Estate Roundtable editions, tap this link.
