Five Years. Three Buyers. Three Completely Different Markets.
After 26 years of selling real estate in the Hamptons, I've learned that markets change, buyers change, and sometimes the way people search for homes changes faster than either. When people ask me how buying a house in the Hamptons has changed over the last five years, they're often expecting a simple answer. The reality is more nuanced. Some things have changed dramatically. Others haven't changed much at all. The biggest shifts I've seen involve the amount of money entering the market, the role technology now plays in the buying process, and how informed today's buyers have become.
Rather than start with statistics, let me tell you three stories.
A Tale of Three Buyers and Sellers
2020: The Covid Frenzy
In late 2020, with COVID in full swing, I represented a property on Ocean Road in Bridgehampton. Ironically, I had previously listed the same property in 2018. At the time, I believed it was priced correctly, but buyers simply weren't in a hurry. The property sat on the market without generating much activity.
Fast forward to 2020. The world had changed overnight. Families wanted out of the city. Parents wanted more space, private yards, home offices, and what they perceived to be a safer environment for their children. We listed the property at an aggressive price. Within 48 hours, it was in a bidding war. Two weeks later, it was closed. That kind of activity would have seemed almost impossible just a few years earlier. At times during COVID, buyers weren't just motivated. They seemed desperate. Fear, uncertainty, and a sudden desire for space created one of the most extraordinary real estate markets I've witnessed in my career.
2024: When Timing Matters More Than Optimism
By 2024, COVID was largely behind us, but many sellers were still looking in the rearview mirror. I represented a charming bayfront bungalow in Amagansett's Lazy Point neighborhood. The house had tremendous character and a beautiful waterfront setting. The challenge wasn't the property. The challenge was pricing. Many sellers who had delayed listing during the COVID years hoped to achieve the same prices their neighbors received in 2021 and 2022. Unfortunately, markets don't work that way. Based on the most recent comparable sales, I recommended a pricing strategy that reflected current market conditions. The seller chose to list the property roughly $1 million above that recommendation. The property sat on the market for seven and a half months. Eventually, it sold for approximately $30,000 below the value I had originally recommended.
I've learned the hard way that the market doesn't care what a seller wishes their house was worth. Buyers determine value, and buyers were telling us something the entire time. The lesson wasn't about the house. It was about timing. Markets change. Buyers change. Inventory changes. One of the hardest things for sellers to accept is that yesterday's market is not today's market.
2026: The Buyer Who Did His Homework
In April 2026, I worked with a young advertising executive purchasing his first home anywhere. He was probably the most digitally sophisticated buyer I've encountered. I sent him six properties to review. The next day, he had gathered virtually all publicly available information on all six homes. Tax records.Sales history.Property details.Neighborhood information.Market data.Zoning information.Everything.Within twenty-four hours, he had already eliminated three properties from consideration without ever stepping inside them. We toured the remaining three. The following week, he revisited two. Shortly thereafter, he made an offer and ultimately purchased one of them. The entire process took about three and a half weeks. What struck me wasn't how quickly he moved. It was how much information he could process before we ever got in the car. Twenty years ago, buyers depended heavily on brokers to gather information. Today, buyers can gather much of that information themselves.
The broker's role has evolved from information provider to interpreter, advisor, strategist, and local expert. Knowledge has always been power. Today, buyers have access to more knowledge than ever before.
Has Wall Street Money Changed the Landscape?
If I had to point to one factor that has had the biggest impact on the Hamptons housing market over the last five years, it would be the amount of money flowing into the market. The pandemic years accelerated a trend that was already underway. Wealth creation, particularly from Wall Street and financial services, fueled an unprecedented run in Hamptons real estate. Buyers who once viewed the Hamptons as a weekend destination suddenly wanted a full-time lifestyle property. Demand surged, inventory shrank, and prices moved higher at a pace many people had never experienced. While the frenzy has cooled, the money has not disappeared. The same forces that drove demand during the pandemic continue to support the market today. The buyer pool remains deep, and many purchasers still view Hamptons real estate as both a lifestyle decision and a long-term investment.
Is AI Already Changing How People Buy Homes?
Five years ago, buyers primarily relied on listing websites, broker recommendations, and traditional online searches. Today, artificial intelligence is beginning to change that process. We're still in the early stages, but the impact is already noticeable. Buyers can use AI tools to research neighborhoods, compare market trends, analyze property values, summarize zoning information, and narrow their search criteria in ways that simply weren't possible a few years ago. As a result, buyers are showing up with significantly more information. That doesn't mean they know everything. Information without context can sometimes create confusion, but it does mean buyers are starting their search from a much more informed position than they once did. I believe we're only seeing the beginning of how AI will reshape real estate search and decision-making in the Hamptons.
Is It True That Today's Buyers Are Better Informed?
One of the most noticeable changes I've seen is how much information buyers have access to before they ever speak with an agent. Five years ago, buyers often relied heavily on brokers to provide market intelligence. Today, they can access:
- Historical sales data
- Market reports
- Property tax information
- Neighborhood insights
- Rental market trends
- AI-generated analysis
- Local zoning and planning information
The amount of information available today is enormous. That has created a more educated buyer, but it has also made local expertise even more valuable. The challenge is no longer finding information. The challenge is knowing which information actually matters. In a market as nuanced as the Hamptons, understanding why one property commands a premium while another sits unsold often requires local knowledge that can't be found in a spreadsheet.
Do Negotiations Depend on the Type Of Hamptons Market You Are In?
People often ask whether negotiation strategies have changed dramatically over the last five years. My answer is usually the same: it depends. Negotiation dynamics are largely driven by the market's temperament at any given moment. In a strong seller's market, buyers tend to compete more aggressively. In a buyer's market, buyers become more selective and negotiate harder. The tactics may evolve, but the fundamentals remain the same. Buyers adjust their offers based on inventory levels, competition, interest rates, and overall market sentiment. What changes is not necessarily human behavior. What changes is the environment in which those decisions are being made.
Is There More Than One Hamptons Market?
One of the biggest misconceptions I see is the idea that the Hamptons operates as a single housing market. It doesn't. There are multiple markets operating simultaneously. The market below $3 million behaves differently from the market between $3 million and $6 million. The $6 million to $10 million segment has its own dynamics. And the market above $10 million often follows an entirely different set of rules. Each segment attracts different buyers, different motivations, and different levels of urgency. That was true five years ago, and it's still true today. When people talk about what is happening in "the Hamptons market," they are often oversimplifying a very complex landscape.
What Hasn't Changed
Despite all the technological advances, market shifts, and changes in buyer behavior, one thing remains remarkably consistent. People still buy homes in the Hamptons for many of the same reasons they always have. They want access to the beaches. They want privacy. They want a place where family and friends can gather. They want a lifestyle that feels different from the pace of city life. Technology may change how buyers search. Market cycles may influence how they negotiate. But the emotional reasons people buy here remain surprisingly constant.
Final Thoughts
The last five years have been a master class in how quickly markets can change. I've seen buyers rush to escape the city during a pandemic. I've seen sellers miss the market by pricing for yesterday instead of today. And I've seen a first-time buyer use AI and digital research tools to evaluate homes more thoroughly than many seasoned investors could have just a few years ago. The common thread is that information moves faster, buyers move smarter, and markets adjust more quickly than ever. The Hamptons have always had a way of humbling people who think they can outsmart the market. But one thing remains true. Real estate in the Hamptons is still local. No algorithm can fully explain why one street outperforms another, why one property receives multiple offers while a similar home struggles to sell, or why timing can make such a significant difference. After 26 years in this business, I've learned that markets, technology, and buyers change.
The value of experience doesn't.
Bill Williams @ Compass East Hampton. Trusted. Devoted. Proven.
