Real Estate Roundtable: Hamptons Horse Sense

Hamptons horses, horse
A new Bridgehampton equestrian community called Windy Hill Farm.
Courtesy of Brown Harris Stevens

While the Hamptons and the North Fork have indeed changed as land has been developed, one cherished part is the equestrian properties. Long a mecca for horseback riding thanks to impressive riders and trainers calling this place home, this trend has only grown. A summer under saddle culminates with the esteemed Hampton Classic Horse Show before many are off to Wellington, Florida, the winter equestrian capital of the world. We asked some of the top agents, some equestrians in their own right, what it is they love about being a part of the equestrian community on the East End and how it impacts the real estate market. What sets this equestrian community apart from others around the country?

Tyler Whitman

Tyler Whitman

“Riding horses is the greatest escape no matter where you are. But there is something extra magical about the Hamptons equestrian experience. Firstly, the facilities somehow manage to feel world-class and beautifully manicured, while simultaneously seeming completely effortless as if it has naturally existed there for hundreds of years — and for some of the farms, that is true! Secondly, during the summer season, some of the top competitors from around the world come here to train. It is really special to get on my horse and be surrounded both by people who are just beginning to dabble in horse life for the first time and also share the ring with riders who have won some of the most competitive trophies in the sport. The combination of those along with all of the amazing people you get to meet and bond over your shared love of horse is truly inspiring.”



Rolanda Blue DoolanDiana Lee Photography

Rolanda Blue Doolan

“I consider myself very lucky to have been an equestrian most of my life growing up between my family’s farms in Sagaponack and Wellington. The equestrian space is a close-knit community like no other. It has taught me from a young age how important hard work, dedication, and loyalty is in all aspects of life. These lessons have also transferred to my real estate business, of course. Through riding, I have met some of my closest friends and have had the opportunity to represent incredible equestrian clients who truly appreciate the beauty and all the Hamptons has to offer. So many see the East End not only as a leisure destination but a place to call home. I have clients who travel from all over the world to be a part of the Hampton Classic. My experience has allowed me to approach the market with an understanding of their unique interests in mind. It’s been exciting to see so many relationships evolve. Those who initially seek short-term rentals for the event, often become seasonal and full-time residents. The caliber of equestrian that competes here can choose to go anywhere they wish, yet they always come back to the Hamptons. In and out of the ring, the friendships made — and the lifestyle available here — are quite simply second to none.”


Susan HovdesvenKind Media

Susan Hovdesven

“I am fortunate enough to keep my horse, Birdie, at the most beautiful stable I have ever seen, Bright Side Farm in Water Mill. The community of riders there are all just good people who love their horses and I am grateful for their friendships. I am a rider on the East End all year long, but there is a fabulous indoor ring that allows for very pleasant winter riding. The population at the barn doubles in the summer with many riders who own a second home and so their horse gets a summer home with large stalls and green spacious pastures. The Hampton equestrian community is unique in that the horses follow their owners when they come for the summer and then leave when their owners leave. All of my equestrian friends own a home in the Hamptons which makes the transition easier for them.”



Chris RitcheyDigital Hoofprints Photography

Chris Ritchey

“The Hamptons equestrian community stands out from other areas across the country because of its rich history of horseback riding. From Jackie Kennedy learning to ride as a child at her family home “Lasata” in East Hampton in the 1930s (recently purchased by Tom Ford for $52 million) to the glitterati-filled VIP tent during Grand Prix Sunday at the Hampton Classic, the history of the Hamptons horse world is a rich one, literally. As the decades have passed, the equestrian scene has evolved. Modern equestrian properties in the Hamptons combine classical architecture with contemporary amenities, catering to riders and their horses. These pastoral estates also add significantly to the value of the surrounding houses — even the non-horsey set pays top dollar for views of open fields, grazing horses and majestic stables. Equestrian properties will always be a part of the Hamptons lifestyle and the region’s timeless charm.”



Hamptons horses, horse
Raquel LopezShawn McMillen

Raquel Lopez

“One of the aspects that makes the East End so desirable and unique is the range of activities supported by the landscape. There are few other places where you can go for a surf at sunrise, play a game of tennis, have lunch on a boat, ride your horse and attend a world-class art opening all in one day! The opportunities for equine activities are a major driver that keep people coming back and wanting to invest in our market. Growing up in Sagaponack, I was fortunate to have easy access to my passion for riding horses. For me, the realization of just how lucky I was to grow up riding on the East End didn’t come until I moved away for college. My leisurely bike ride or walk to the barn turned into a 45-minute commute, making daily rides out of the question. This gave me an even greater appreciation for my summers spent riding, working and competing in Bridgehampton. Having the Hampton Classic in our backyard gives local riders and spectators incredible access to the top talents of the equestrian world that most others would have to travel great distances to experience. When I moved back to Sagaponack, I transitioned my career from the equine industry to real estate while continuing to train and sell horses on the side. Over the past six years of growing my career, being an expert in the local equestrian scene helped me recommend locations for families to be close to their favorite horse farms, as well as provide tailored recommendations for pony camps, professional trainers, and other local equestrian activities.”



Robert NelsonESI Horse Show Photography

Robert Nelson

“I have been a rider since I was 9 years old. My first horse was Thunder, a 15-hand mix breed that my sister and I talked our father into buying. Thunder started us into the world of horsemanship with our first, long trail rides, then pony club, and eventually by showing, and learning everything about horse ownership. Later I would go on to 3-day eventing and eventually the love of dressage. As a young adult living in New York City, I would sometimes ride a horse from the Claremont Stable into Central Park to get my “fix.” It was trips to the East End later on that I returned to full-time riding. The fact that there were stables, partly due to the preservation of the farmland open space needed for stables and pastures that allowed for equestrian activities in the Hamptons. I always end the summer going to the Hampton Classic, now an observer, and enjoy being inspired by not only the young people beginning in the sport but also the worldclass competitors — the best of show competing in our backyard. The Hamptons have and will continue to inspire equestrians from various age groups, highlighting a sense of shared unity and shared experiences across generations.”

This article appeared in Behind The Hedges issue on September 1, 2023. Read the full digital edition here. Be sure to check out more Real Estate Roundtables