Everyone talks about summer in the Hamptons. I’ve always thought fall deserves a better publicist.
From Labor Day through Thanksgiving, the Hamptons settle into one of its best stretches of the year. The beaches are still beautiful, getting a dinner reservation no longer requires an act of Congress, the farm stands are overflowing, and you can actually drive from East Hampton to Bridgehampton without questioning every decision you’ve made in life. It also happens to be one of my favorite times of year for real estate.
After more than 26 years selling homes in the Hamptons, I’ve watched the same general rhythm repeat itself. Spring gets busy as everyone gears up for summer. July and August can be active, but people are also trying to enjoy their houses, their rentals, the beach and their vacations.
Then Labor Day arrives. Suddenly, people get serious. Buyers who spent the summer thinking about owning start looking with more purpose. Sellers who have been considering a move decide they don’t want to wait another year. Properties that have been sitting on the market get a second look. New inventory comes on. And we have a fairly short window to get things done.
In my book, the real fall market runs from Labor Day through Thanksgiving. After Thanksgiving, things slow considerably until the market begins waking up again around March.
That roughly 12-week period can be a very good time to be on either side of a Hamptons transaction.
The Hamptons Market Is Still Strong, But Buyers Are Smarter
The enormous run-up in Hamptons real estate since 2020 changed the market. Recent reporting puts the increase in the median Hamptons sale price at roughly 60% since 2020. But this isn’t 2021 anymore. Buyers have more information, they’re more patient, and they generally know what comparable properties are selling for before they ever walk through your front door. At the same time, good inventory remains relatively limited. That creates an interesting fall market. A well-located, well-presented home that is priced correctly can still get plenty of attention. An overpriced house can sit there looking lonely while buyers drive right past it. Fall tends to expose the difference rather quickly.
Why Fall Works for Sellers
The biggest advantage for a seller is simple: the buyers looking in October generally aren’t sightseeing.
By fall, many buyers have spent months following the market. They know Wainscott from Water Mill. They understand what south of the highway costs. They know the difference between a house that needs $200,000 worth of work and one that needs $800,000 worth of work, although sometimes I have the pleasure of delivering that news. More importantly, many fall buyers want to get something accomplished. They may want to close before year-end. They may have spent another summer renting and decided they’re finished writing large rental checks. Or they may simply want to buy now so the house is ready for the following summer. For sellers, that motivation matters. There is also typically less competing inventory than during the big spring listing push. You don't necessarily need 50 buyers walking through your house. You need a handful of qualified buyers, and ultimately you need one who really wants it.
Why Fall Works for Buyers
Buyers get a different advantage. By September and October, the market has had time to reveal itself. A property that came on in May at an ambitious price may suddenly have a more realistic seller behind it. A house that seemed untouchable in June may still be available. Price reductions begin appearing. Sellers start thinking about carrying a house through another winter and relaunching it in the spring. That doesn't mean every fall seller is desperate, far from it. It means there's more room for an intelligent conversation about price and terms.
Fall also gives buyers a chance to see the Hamptons as it really is. You see the house without hydrangeas doing half the marketing. You can judge the light, privacy, heating systems, drainage, landscaping and how the property actually feels when it isn't 78 degrees and sunny. That's useful information when you're spending a few million dollars.
Five Questions Buyers Ask Me About Buying in the Fall
1. “Will I get a better deal after Labor Day?”
Sometimes.
A seller who has been on the market all summer without selling may be more receptive in October than they were in June. Days on market, price reductions and the seller's motivation all become important negotiating tools. But don't confuse fall with a clearance sale. Great Hamptons properties in great locations still command strong prices.
2. “Should I wait until winter when things are even quieter?”
You can, but your choices may shrink considerably. Once we get past Thanksgiving, the Hamptons sales market traditionally slows until roughly March. Some sellers withdraw their homes and wait for spring. So waiting may improve your negotiating position on one house while eliminating five others from consideration. I generally prefer having choices.
3. “Is there more inventory in the fall?”
There is often a fresh batch after Labor Day. Some homeowners want to enjoy one last summer before selling. Others make the decision during August that it's time to move on. At the same time, you'll still have properties left over from the spring and summer market. That combination can make September and October particularly interesting.
4. “Why not just wait until spring?”
Because everyone else knows about spring too. Spring can bring more inventory, but it can also bring more buyers. If the right house is available in October, I wouldn't lose it simply because the calendar says April sounds more traditional. The best time to buy a great property is usually when the great property is actually for sale.
5. “Can I realistically buy now and have the house ready for next summer?”
Absolutely, and that's one of the best reasons to buy in the fall. Close in November or December and you've given yourself several months to paint, renovate, landscape, furnish, add the inevitable Sonos system and spend considerably more money at the hardware store than you originally planned. When Memorial Day arrives, you're ready.
Five Questions Sellers Ask Me About Selling in the Fall
1. “Did I miss the market by not listing in the spring?”
No. The Hamptons has a very real second selling season after Labor Day. In fact, historically September and October have been active transaction months on the East End. You missed the spring market. You didn't miss the market. There's a difference.
2. “Are there really buyers around after Labor Day?”
Yes, and increasingly so. The Hamptons season has stretched well beyond Labor Day. More homeowners stay longer, restaurants and businesses remain active, and fall weekends have become busy in their own right. More important for a seller, the people touring houses in October are generally there for a reason.
3. “Should I price high and see what happens?”
You can. I just wouldn't recommend it. Today's buyers have access to enormous amounts of information. If the last three comparable properties sold around $4 million, putting yours on at $5.5 million doesn't make it worth $5.5 million. It makes the other three houses look like bargains. Fall is relatively short. I would rather price a property where buyers recognize the value and create some urgency than spend October explaining why nobody has made an offer.
4. “Does my house show as well in the fall?”
Often, it shows better. The Hamptons in September and October is beautiful. Gardens are still alive, lawns are green, the light is terrific and the leaves are beginning to turn. It also allows a house to show another side of itself. Fireplaces matter again. Kitchens and dining rooms feel inviting. Libraries, dens and finished lower levels become more relevant. Buyers begin thinking about Thanksgiving weekends, Christmas, winter dinners and using the house throughout the year. That's a powerful shift from simply selling the swimming pool.
5. “What happens if we don't sell by Thanksgiving?”
Then we make a decision. We can keep the property on through the winter, adjust the price if the market is telling us something, or take it off and prepare for a March relaunch. What I don't like doing is drifting into December without a strategy. Real estate rarely improves through wishful thinking.
The 12-Week Window
This is what makes fall different in the Hamptons. There is a natural deadline. Labor Day → September → October → Thanksgiving. Buyers know winter is coming. Sellers know the market is going to slow. Brokers know we have a relatively short runway to put deals together. That creates urgency without the frenzy that sometimes comes with spring and early summer. And I like markets with a little urgency. After Thanksgiving, things don't stop completely. Good properties sell twelve months a year in the Hamptons. But activity typically drops off substantially during December, January and February before the traditional spring market starts to build again in March. So if you've been sitting on the fence, fall is worth paying attention to.
Buying and Selling at the Same Time? Fall Gets Even More Interesting.
This may be where the fall market makes the most sense. If you're selling one Hamptons house and buying another, you're participating in the same market on both sides. You may give a little on your sale and make it back on your purchase. Or you may sell into limited inventory while finding a seller who has become more negotiable after sitting through the summer. I tell clients not to become obsessed with “winning” one side of the transaction. Look at the entire move. If selling for 5% less allows you to buy the house you really want for 8% less, that's a pretty good day's work.
So, Is Fall Really the Best Time?
There isn't one perfect month to buy or sell every Hamptons property. A great oceanfront house doesn't suddenly become less desirable because it's October. A badly overpriced house doesn't become a bargain because the leaves changed color.
Price, location, condition, scarcity and current market conditions still determine value.
But from Labor Day through Thanksgiving, we get an unusual combination: motivated buyers, motivated sellers, new inventory, older inventory, fewer distractions and a natural deadline. That's why, year after year, I consider fall one of the best opportunities in Hamptons real estate. And there is one final advantage. You can tour five houses in East Hampton and Amagansett on a Saturday and still make your dinner reservation.
Try doing that in July.
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