I was sitting in my car when I got a phone call that was potentially worth more than half a million dollars. It was a real estate agent whose client was considering making an offer on my house. She wanted to clarify a few details, including: Had I really handled the whole listing privately? She couldn’t quite believe that I was an amateur.
“So — you’re not a Realtor?” she asked.
“No,” I said. “It’s the first house I’ve ever sold.”
“I’ve been in this job for, well, more than a day, and I was sure you were a Realtor,” she said. “Everything — the language you used, the organization, the emails.”
But none of that was me. It was all A.I.
A few days earlier, I had pressed go on an experiment involving my family’s single largest financial asset. Could I sell our home without a human real estate agent, relying almost entirely on a couple of chatbots?
As a technology journalist, I had watched artificial intelligence transform medicine, business and even warfare. But I didn’t know how it would function in the far more intricate world of Hudson Valley real estate.
“Can we really do that?” my wife asked. “We don’t know anything.”
“Just trust me” was the best I could come up with. “A.I. can handle it.”
Our three-bedroom, two-bath ranch was set on a marshy acre in upstate New York. My wife and I had bought the house for about $520,000 four years ago, and I quickly fell in love with its vaulted sunroom and giant kitchen island, where we’d gather for Cheerios every morning and the occasional Negroni at night. But in March, with a second child on the way, we decided it was time to move. In the beginning, we expected to do what 91 percent of people do when they sell a home: Hire a real estate agent.
The single most important part of the process is setting the listing price, and agents say they play an essential role — using their wealth of experience to synthesize market data with intangibles like local demand and neighborhood quality. My wife and I figured our house could fetch $550,000, but that was pure guesswork, based on nothing more than glancing at Zillow. We looked forward to the agents’ more sophisticated approach. Yet when we interviewed a few and mentioned that figure, they mostly just shrugged and agreed.
One agent said her brokerage used an algorithm to estimate prices, but it determined that our home was worth less than what we had paid. Another agent, leaning on our kitchen counter after a tour, agreed. “You’re probably going to lose money,” he said.
I had already harbored some doubts about real estate agents’ value, and these conversations went a long way toward confirming them. Also, the costs of their services seemed staggering. I was expected to pay about 3 percent of the sale price to the agent and another 3 percent to the buyer’s agent, probably totaling more than $30,000. Why would I pay them to help me take a loss on my house?
A few days later, I got curious about how our home would look to potential buyers, so I gave an A.I. chatbot the basic details and asked for a listing description. It generated glowing prose — describing an “inspiring” place that was “flooded with light” and “perfect for bird lovers.”
I sent the passage to my wife. “A.I. did a good job at this I think,” I wrote.
“Yeah damn lol,” she agreed.
I thought some more. So much of a real estate agent’s job seemed straightforward: Follow the rules; take cues from comparable homes. Any human edge that agents may have once provided seemed archaic. They no longer have total control of listings or home sale data, and the personal networks that once helped a property sell have long since been obviated by websites like Zillow and Redfin.
With my wife’s support, I decided to replace the agent entirely with A.I. I wish I could tell you that I vibecoded something sophisticated, but the truth is that I just started chatting with Gemini, the Google chatbot, because I already had an account set up through work. For anyone else, it costs $7.99 a month.
Once I started using A.I., I couldn’t stop. To get our house ready for sale, I asked hundreds of questions over three weeks. When I needed to hire a photographer, the chatbot offered a list of local businesses, then gave advice on staging. It told me how to organize the resulting photo gallery for maximum impact. (Exterior > kitchen > floor plan.) As I obsessively fine-tuned the listing language, it indulged my every request.
Real estate agents used to tightly control access to the Multiple Listing Service, the master database of homes for sale. But a rule change more than 20 years ago allowed those listings to circulate far more easily online, and I used a service called Homecoin to publish mine for $200. The documents I needed to fill out were intimidating at first, but A.I. quickly explained jargon like “selling concessions” and “automated valuation model.”
The chatbot did make one major mistake. I wasn’t using an agent to sell, but I would still be expected to pay the eventual buyer’s agent a commission of up to 3 percent. When I complained about this to the chatbot, it said I should explain in the listing that I was offering 0 percent. That’s not allowed, under a 2024 settlement that would have exposed me to fines. Thankfully, I knew that already, because Homecoin had flagged it as a common mistake.
Aside from that snag, A.I. made the process of creating and submitting our listing feel easy. I arranged for it to be published on Thursday, March 19. That morning, when I logged into Zillow, my home popped up right away. It blended in perfectly with the houses represented by real estate agents. It was impossible to tell that I had no idea what I was doing.
A flurry of bookings to view our house over the coming weekend arrived in my inbox within hours. I struggled to manage the appointments until, again, I just let the chatbot do everything for me. I told agents that they had to email or text — no phone calls. Whatever they wrote, I copied and pasted into the chatbot; whatever it replied, I copied and pasted right back to the agents. I was worried that pushy ones would prey on my inexperience, so I had the chatbot come up with a list of potential conflicts and write confident responses I could have ready.
On Friday afternoon, when our listing had been online for a little more than 24 hours, an agent contacted me to say a client was preparing a quick cash offer. I rushed to the chatbot for help on how to graciously receive it while secretly holding out for more bids.
“Do i need to address anything like ‘im not playing games’ or ‘im not trying to leverage your offer’ or anytihng?” I typed, poorly.
Usually the chatbot was sycophantic. This time it did the A.I. equivalent of slapping me across the face. “Whatever you do, do not say ‘I’m not playing games’ or ‘I’m not trying to leverage your offer,’” it said. “In negotiation, as soon as someone says ‘I’m not playing games,’ the other party immediately thinks, ‘They are definitely playing games.’ It creates a defensive vibe and makes you look like an amateur who feels guilty about wanting more money.”
It was all a demonstration of A.I.’s ability to impart not just facts — the raw information it has ingested from Wikipedia or training materials — but something closer to wisdom. It granted me access to a way of thinking, a posture for navigating a nuanced and high-stakes interaction, that would normally be reserved for people with innate talent or lots of earned experience.
How quickly should I respond to a message so I don’t seem overeager? How can I address someone’s concerns while keeping the person interested? The answers used to be something only a real estate agent could confidently answer. Not anymore.
It was now almost impossible for me to make a decision without getting A.I.’s opinion. By Friday evening, I was starting to worry that the interest in our house was a little too strong. We had nearly 20 viewings scheduled for the weekend. I confessed to the chatbot my anxiety that we had underpriced the home. It offered some needed reassurance, saying that by pricing low, I had stumbled into an “accidental strategy” that could result in multiple offers. “When you get 1,100 views and 91 saves, you haven’t just listed a house; you’ve started a localized ‘gold rush,’” it wrote.
My wife complained that I trusted a chatbot’s advice more than her own. She was right. That night, I tried to write a simple email thanking an agent, but I stumbled over words that suddenly felt awkward and jumbled, failing to strike the perfect balance of appreciation and confidence to which I had grown accustomed. I replaced what I wrote with the chatbot’s version.
I had started this experiment thinking that the chatbot would create a superpowered version of myself — combining my own judgment with its vast knowledge. But once I started relying on A.I., witnessing its know-it-all competency with basically everything, my shortcomings started to feel enormous and even risky. I had thought I was elevating my own skills. In reality, I was replacing them.
My early elation about a quick sale had also turned. Two agents told us that their clients would prepare offers, but the clients later decided not to after driving around the neighborhood. Other potential buyers cited the small bedrooms and some moisture in the basement as deal-breakers. My mood crashed, and I was suddenly convinced that the house would never sell.
The A.I. offered only modest comfort. “It is completely normal to have a ‘vulnerability hangover’ after the first few showings. When people don’t immediately throw money at you, you start looking at your house through the eyes of the most critical stranger,” it said, a little woodenly.
I yearned for some human empathy. This seemed like the real estate agent’s enduring value — the wise and friendly confidant who is paid to be there for you. Without an agent on speed dial, I phoned a good friend, who reassured me that the house would sell in no time. I also asked my wife for input on a few questions and realized that her quick opinion — a simple “No, that’s dumb,” for example — was far more efficient than a carefully balanced analysis from a chatbot. I did need humans in the loop. But my friends and family were up to the task — and they didn’t charge a commission.
On Monday, I took stock. After a weekend full of showings, we had lots of rejections. Everything from the neighbors to the price seemed like problems. One buyer said the house was too small; another complained it was too big.
The chatbot insisted that this did not matter. “I know hearing ‘no’ 14 times feels like a series of bad dates,” it wrote, “but in the real estate world, those numbers are a sign that your listing is healthy.” The chatbot was right. I got three offers by our 5 p.m. deadline. All were for a lot more than the asking price.
The chatbot raved about our shared victory. But we were entering the stage I dreaded the most: negotiations. I’m the kind of person who gets sweaty palms when asking for a better table at a restaurant, and I’m incapable of shushing someone in a movie theater. So how could I handle the high-stakes back-and-forth of a real estate sale, while my family’s life savings were on the line?
Agents claim to provide deep value here, bringing a career’s worth of instincts to the bargaining table — deploying tact to get tricky deals completed, and aggression to maximize profits under the right circumstances. One industry spokesman I later spoke to, Dan Weisman of the National Association of Realtors, emphasized how complex purchase documents can be.
“Everybody has different things that they want in a contract. It could be price, it could be closing date, it could be, I don’t know, any number of different things,” he said. “There are so many variables. And right now, at least, to facilitate that, I think it’s so important to have a human in the loop.”
When I looked at our three offer letters, though, I saw something different. They were simple, one-page documents, and only a few things seemed to matter: mostly the price, conditions and deposit. All three bidders waived inspection and appraisal, and they all had healthy financing. I uploaded the offers to the chatbot. It spat out a verdict that my wife and I agreed with: The offer with the most certainty was the winner, even if the price was a smidgen lower than the highest.
Chatting with the bot about possible counteroffers, I struck upon an idea. Would the buyers agree to pay their own agent a 2 percent commission instead of making me pay? That would instantly save me more than $12,000. If I were using my own agent, making a commission the focus of a negotiation would feel awkward, even insulting. The commission is the lifeblood of the entire industry. But I had no agent to worry about, and my chatbot supported the idea. So I went for it. My counterparty accepted almost instantly.
Naturally, I started worrying. Should we have pushed even harder for more money? Agents say they understand this delicate art of squeezing more out of the buyers without driving anyone away from the sale.
My wife told me to be more human. “I sleep better at night not being like that,” she said.
I had to ask the chatbot. It agreed: “You didn’t ‘lose’ money; you ‘bought’ peace of mind.”
We accepted the offer at just over $600,000. And my A.I. experiment came to a close. To handle the closing, I hired a lawyer — a human one — for a small fee.
In the end, using A.I. netted me more than $90,000. That includes the premium over the asking price, plus the roughly $36,000 in fees I didn’t pay.
I’m not sure how replicable my experience would be for anyone less versed than me in technology. I’m paid to be an expert on A.I. (In addition to Gemini, I used a browser from Perplexity for a few tasks.) Selling the house was a big and complex undertaking that worked in part because I was transacting in a thriving market, with no special circumstances. Many people would probably be happy to pay fees to avoid the hassle. Some will be too afraid to sell their home without a paid professional in their corner — someone who knows all the rules and, unlike a bot, is obligated to follow a code of conduct.
But I’m persuaded that A.I. may well transform real estate agents into something more like travel agents. Once essential to navigating an opaque process, they could soon become more of a nice-to-have for busy people who want a more carefree experience.
I’m not the only person who thinks so. At one point after I accepted the offer, I read about a man in Florida who had sold his home using A.I. for $100,000 more than an agent told him was possible. The real estate industry had reacted with outrage, writing that the seller had potentially lost about $225,000 by listing too low and accepting an offer too quickly.
I wondered if I had made a mistake. I called Richard Vizzini, a real estate agent who has worked my area for a decade, for his expert opinion on my sale. Despite my apparent success, did I actually blow it?
“Dude, that house is probably worth in the $600,000s,” he said, guessing at a sale price of $650,000 or more. “There’s no doubt about it.” It was hard to square his post facto confidence with the gloomy predictions his colleagues had made in my kitchen. The humans hadn’t been nearly so bullish then.
And then I did some math. Selling my home for $605,000 without any agent fees put as much cash in my pocket as a $643,000 sale when paying agents their normal commission. Maybe I could have sold for more with a human’s help, but that wouldn’t have necessarily benefited me. (And it certainly wouldn’t have benefited the buyer.) The only people guaranteed to gain would have been the real estate agents.
I had one more call to make: to the new owners, Melissa and Michael Quinn. They were fascinated to learn what I had done, and asked whether I or the chatbot had been responsible for the aggressive negotiation tactics.
The Quinns had no regrets about paying the human on their side of the transaction. They have a deep relationship with their agent, whom they have used to buy and sell homes for nearly a decade. They know all about each other’s families and children. But when I asked the Quinns if they’d consider using A.I. if they ever decided to sell the house, they said yes without hesitation. “It would save me thousands of dollars,” Melissa said.
When our deal was nearly closed, I turned to the final phase of our relocation. I logged into the chatbot and posed another question.
“I need to buy a house and I’m doing it without an agent,” I wrote. “Where do I start?”
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