There’s something special about life on the East End during fall and winter, whether it’s the chance to take in the vineyards and holiday festivals or simply the solitude of the beaches and endless access to shopping, entertainment and dining. Yet it’s also the perfect time of year to explore other environs, whether as a renter or as a second (or third or fourth) homeowner in areas where sand and sun or snow reign supreme. With summer in the rear-view mirror, our panel of experts from the local market and further afield share their insights into key points for buyers and sellers in the Hamptons, on the North Fork and beyond.
“The fall is my favorite time of the year on the North Fork. There is an endless list of things to do and enjoy during the harvest season. The vineyards are abuzz. It’s a tradition in my family to go apple picking and then come home and make applesauce together like I did with my grandmother when I was a kid. We also enjoy pumpkin picking and making jack-o-lanterns. The farms are full of corn mazes and pony rides and all sorts of activities. The farm stands are full of fabulous local produce for farm-to-table meals to be enjoyed with family and friends. As we head into winter the numerous opportunities present themselves to enjoy the rich history of each of the hamlets in their holiday festivals. It’s a wonderful place to escape the chaos of the city to select and cut your own Christmas tree, or do your holiday shopping in all of our unique little shops and boutiques that offer personalized service and that hometown warmth you can’t find anywhere else. At the end of your day exploring the beautiful North Fork, come home, light a fire and enjoy a cup of cocoa snuggled under a cozy blanket with the ones you love.”—Donielle Cardinale, Licensed Associate Real Estate Broker, Daniel Gale Sotheby’s International Realty
“Like many people, I think fall is one of the most beautiful times of year to enjoy a property. The weather is still great, the colors are beautiful, and the crowds are largely gone. As you head into winter, we recommend that buyers purchasing a home ask for a pool letter and sprinkler letter from the seller that ensures the pool and sprinkler system was in good working order at the time of closing. Sellers should try to keep their pools open as long as possible—as a house shows better with an open pool. They should also stay on top of fall cleanups and remember to engage a snow removal company early in the season. We can’t sell a house if snow blocks gates, driveways and front doors…. I love Aspen for skiing, Miami for sun and fun, and New York City for its energy and excitement. But no place is better than the Hamptons!”—Enzo Morabito, Licensed Associate Real Estate Broker, Enzo Morabito Real Estate Team, Douglas Elliman Real Estate
“Fall on the East End is my favorite time of the year. The ocean waters are still warm, the light is incredible, the crowds are gone, which makes driving a breeze, and getting a reservation at Nick & Toni’s won’t take three weeks. Indian summer is harvest season, so those of us who garden are reaping the fruits of our labor—literally—and those who love to fish will find a bounty of opportunities. Oh, and real estate-wise, it is the height of the busiest selling season! Sellers put the apple pie in the oven and go downtown shopping while your realtor does an open house. Buyers—fall is our busy season, so if you are ready to make a great investment, pull the trigger now. Sales made now will close in winter, which is perfect to give the seller time to move out and the buyer time to personalize their new home and have it ready for springtime. The winter out east reminds me of a Norman Rockwell painting—ice skaters on Town Pond, sledding on Quail Hill, hiking the waterfront on North Haven. The holidays are a quiet time for residential but the busiest time for commercial, as shops and restaurants need the winter to get ready for Memorial Day business!
As an avid skier, my passion takes me out west every winter—which is ideal for my business, as that is the slowest time of year for Hamptons real estate. I’ve thought many times about buying but I can’t decide between Colorado, Utah, Wyoming or California, so I guess I will keep kicking those tires until I can grow up and decide. In the meantime I will keep my investment dollars in my East End dire—it’s done me well.”—Judi Desiderio, CEO, Town & Country Real Estate
“Fall in the Hamptons is my favorite season. The leaves are turning, traffic is down and the beaches and bays are still the most beautiful in the world. If you are in the market to buy a home, winter is the best time to look at Hamptons real estate. Many potential buyers have gone south yet there are always homeowners that must sell in a timely manner. Dress warmly, be courageous and you may just land the home of your dreams. If you are considering investing in another vacation locale, I suggest Aspen, Colorado. There is consistent demand from buyers and the rental market is strong. Like the Hamptons, values go up over the long-term. Aspen is not only for skiing. In the summer months it is a cultural Mecca. What can be better than listening to music on top of a mountain?” —Alan Schnurman, Licensed Associate Real Estate Broker, Saunders & Associates
“When buyers think of the Hamptons they normally think ‘summer.’ The big surprise is that the fall months may be considered the best of the year. Our weather is gorgeous, and there’s plenty to do for adults and children alike. Enjoy the harvest with pumpkin picking and corn mazes. Relax at your favorite vineyard and enjoy live music and wine tasting. Enjoy holiday parades and festivals with family and friends. The Hamptons—we live on vacation!”—Terry Thompson, Licensed Real Estate Salesperson, Douglas Elliman Real Estate
“Having a property for the fall and winter gives you entirely separate chapters of enjoyment to your coveted ‘Hamptons lifestyle.’ Experiencing the breathtaking autumn foliage, uncluttered roads, ease of getting a great spot at your favorite restaurant and solitude on a gorgeous beach are the rewards, along with spending more quality time indoors in your East End home. It can also be a good time to sell a home during this period, because generally those that are looking to purchase one are statistically more serious to buy and the focus is on the home search and not competing with beach time and all-day outdoor activities. Also for buyers who are looking to purchase, make your offer fair, educated and researched; there may be snow on the roof, but that does not chill the value of a perfect home. It’s also truly a great time to do a site visit at a home being newly constructed. Being able to provide a builder with a punch list this time of year affords the ability for a seamless spring occupancy. But remember, don’t procrastinate to buy because it’s ‘off-season’—spring will arrive before you know it and with that you may be caught in a bidding war for the same property if you wait till then.”—Jim Rooney, Principal, FLEXdevelopment/KP Property Group Inc.
“What’s so special about owning a property on the East End during the fall and winter is that it’s just a great time to enjoy all that the Hamptons offers. Obviously, the crowds have subsided, which means it’s easier to make reservations to enjoy all of the great restaurants that abound out here. Traveling from Montauk to Southampton is a breeze. A brisk walk on the beach is so refreshing and mind-altering, especially since it’s easy to park your car now. As for buyers and sellers during these seasons, it used to be in the past that this was the time to scoop up a deal for the buyer. Granted, there is a slowdown in the market during the holidays, but not like it was years ago. It’s actually a great time for potential buyers to be looking. The laidback feel brings back a time of yesteryear, when the Hamptons were like that all year round.”—John Christopher, Licensed Associate Real Estate Broker, Brown Harris Stevens of the Hamptons, LLC
“The East End is remarkable ‘after season.’ The fall color and myriad activities available for families are harder to experience, if at all, in the city. Halloween is especially wonderful for children, since the villages really turn out for daytime costumed parades and events, closing off streets and making trick-or-treating very special. It’s kind of old-fashioned, and kind of marvelous. The same goes for the autumn corn mazes, apple picking, and the ever-popular Pumpkintown. As the weather grows colder, people use their homes to host Thanksgiving dinners, and that merriment lasts straight through the mid-winter celebrations. The fall and winter light across the land are as beautiful, although in different ways. The days are shorter, the villages are quieter, and there is something peaceful and calming about the change of seasons. It offers a real respite from an otherwise hectic life. We have noted in more cases than not, that once folks buy a house in the Hamptons, they may come out as often as 50 weekends per year.
There are defined advantages to buying ‘off-season.’ Customers looking to buy during time periods when the leaves have fallen off the trees and hedges can see the land parcel boundaries more clearly, or how near or far the neighbors properties run. And on the ocean, customers can see firsthand how the elements can affect homes. These can be important considerations for a customer’s decision to purchase.”—Holly Hodder, Licensed Salesperson, Sotheby’s International Realty
“South Florida is the ‘it’ winter destination for a tremendous number of Long Island natives, who escape the chilly northern winters by indulging in the tropical climate of the Palm Beach, Fort Lauderdale and Miami markets. With miles and miles of pristine beaches, the warm Atlantic waters, an average winter temperature near 80° and cultural attractions galore, South Florida is more popular than ever. For Long Islanders, South Florida boasts world class country clubs, championship golf, five-star shopping, three international airports and a carefree lifestyle that is second to none.”—Ben G. Schachter, LCAM, GRI, Broker-President & Licensed Real Estate Instructor, The Signature Real Estate Companies
“Long known as ‘The Hamptons of Florida’ for its laid-back, unpretentiously elegant island vibe, Vero Beach is an ideal winter community for several key reasons that distinguish it from other options. Tucked just inside the line of the tropics, Vero rarely sees a hard frost. As a result, Vero is home to both ancient Live Oaks, tropical palms and 28 miles of pristine Atlantic Beaches. A jacket is a Vero fashion accessory, not a necessity! And with direct flights from Vero municipal airport to the New York area starting December 10 for under $200 round trip, getting to Vero is a breeze. Vero property is 40% more affordable than other seaside communities throughout Florida and the Eastern seaboard. From waterfront homes on the barrier island or a mainland pied-a-terre, Vero buyers simply get more bang for their buck.
Low density, low profile zoning has been in place in Vero since the 1970s, in which condos may not exceed four stories and homes have strict height limits. This visionary policy has kept sprawl away, resulting in finite housing inventory and a barrier island with fixed bridges that comprised a charming Ocean Drive retail district and largely single family homes whose beaches, restaurants, waterways and roadways remain remarkably un-crowded—even during peak visitor season of January through March. The jewel of Vero Beach may well be its beloved Indian River Estuary. Serving as Vero’s intra-coastal waterway, the Estuary’s brackish, tidal waters are dotted with Mangrove-lined spoil islands, preserved from development. The River is home to a bevy of species from manatees to bottlenose dolphins, egrets, bald eagles and heron—but happily, rarely gators, who dislike its brackish waters. A variety of public, free-of-charge accesses to both the beach and Indian River are accessible to residents and visitors for fishing, tubing, SUP and boating adventures.”—Sally Daley, Broker/Owner, Daley & Company Real Estate, Vero Beach