Real estate CEO Ryan Serhant posted in March on Instagram about ChatGPT disrupting a $50 million property deal, stating both the seller and buyer used the AI tool to evaluate the agreed price and received conflicting guidance that nearly derailed the transaction. Serhant explained he salvaged the agreement by clarifying AI limitations, including its inability to assess off-market comparables, replacement costs, or buyer intentions. Industry executives including Coldwell Banker Realty CEO Kamini Lane report increasing client reliance on AI tools like ChatGPT and Claude for pricing decisions, while Zillow recently launched an AI mode feature building on its 2006 Zestimate tool to provide personalized buyer guidance using floor plans and 3D property captures.
Serhant Reports ChatGPT Disrupting $50 Million Property Transaction
Ryan Serhant posted a video in March on Instagram titled "ChatGPT just blew up my $50M deal," explaining he had brokered an agreement on a property when the seller used ChatGPT to ask if he should sell at the negotiated price. Serhant stated ChatGPT told the seller not to accept the price, indicating the property was worth more. The buyer then consulted the same AI tool to determine if he was overpaying, and ChatGPT confirmed he was paying too much. Serhant said the tool "gave him comparables that showed why, without context and without actually understanding the property." The post received more than 3 million views.
Serhant stated in a subsequent post he salvaged the deal by explaining to both parties that AI "doesn't know the future, it can't predict the future. It doesn't know intentions, doesn't know emotions, doesn't know what buyers are circling, doesn't know off-market comparables, doesn't understand, fully, replacement costs, and doesn't actually optimize for the deal." He concluded that "AI can model a market. It can't model a deal." Serhant launched his own AI-powered workflow automation platform called S.MPLE, which he discussed on the Property Play podcast.
Coldwell Banker CEO Warns AI Misses Neighborhood Nuances
Kamini Lane, CEO of Coldwell Banker Realty, stated her agents are observing more clients—both buyers and sellers—consulting sources like Anthropic's Claude and OpenAI's ChatGPT to price homes or calculate offers. Lane said these generalized large language models miss nuances of individual homes, neighborhoods, and clients. She stated, "Market analysis, comparative analysis, those are key tools in a real estate agent's toolbox. But the important thing is that those are starting points for an agent to then apply their judgment, their expertise, their nuanced understanding of the real estate market."
Lane emphasized that agents can identify emerging neighborhoods and design features through conversations, stating this "anecdotal data that agents are aggregating through their conversations, that is something that no AI tool is ever going to be able to aggregate in the same way that a real estate professional can." She expressed concern that AI cannot distinguish between what clients need versus what they say they want, and noted that "artificial intelligence is trained to be sycophantic, it's trained to give you the answers that you want, so that you will continue to engage, and so AI is more likely to give you the price that you want versus the price at which a home is going to sell for."
Zillow Launches AI Mode for Personalized Buyer Guidance
Zillow launched its Zestimate feature in 2006 alongside its website launch. The company recently introduced "AI mode," designed to guide homebuyers through property searches by learning their specific needs and enabling personalized conversations with the Zestimate. Nicholas Stevens, vice president of product and AI at Zillow, stated, "AI guidance for consumers needs to be connected to real context, real data, real ability to take action. Then that AI guidance needs to be deeply connected to what a real estate agent is attempting to do."
Agents must upload detailed floor plans and 3D visual captures of entire homes and surrounding lots with comprehensive information. Stevens explained that in AI mode, Zillow provides offer advice to buyers, stating the system "actually sees a remodeled kitchen. It actually sees upgrades in the house, and that's useful, both for buyers but also homeowners thinking about selling or remodeling as well." Zillow's AI feature currently focuses on buyers, and Stevens said the company will roll out a tool for sellers.
Industry Executives Raise AI Accuracy Concerns
The implementation of AI pricing tools raises accuracy questions about how AI systems understand human users. Lane stated she worries AI cannot identify what buyers and sellers need compared with what they express wanting. She noted AI may not provide difficult advice that human agents must deliver. Stevens acknowledged the importance of connecting AI guidance to "real context, real data, real ability to take action," distinguishing Zillow's approach from "a third-party, generic experience."
FAQ
What did Ryan Serhant say ChatGPT did to his $50 million property deal?
Ryan Serhant posted in March that ChatGPT nearly derailed a $50 million deal after both the seller and buyer used the tool to evaluate the agreed price. ChatGPT told the seller not to accept the price and confirmed to the buyer he was overpaying. Serhant salvaged the agreement by explaining AI limitations, including its inability to assess off-market comparables, replacement costs, and buyer intentions.
How does Zillow's AI mode feature work for homebuyers?
Zillow's AI mode, recently launched, guides homebuyers by learning their specific needs and enabling personalized conversations with the Zestimate. Agents upload detailed floor plans and 3D visual captures of homes and lots. Nicholas Stevens, Zillow's vice president of product and AI, stated the system identifies features like remodeled kitchens and upgrades to provide offer advice to buyers.
Why does Coldwell Banker's CEO warn against relying on AI for property pricing?
Kamini Lane, CEO of Coldwell Banker Realty, stated AI tools like ChatGPT and Claude miss nuances of homes, neighborhoods, and clients. She explained agents can identify emerging neighborhoods and trends through conversations, which AI cannot replicate. Lane also stated AI is "trained to be sycophantic" and provides answers users want rather than accurate pricing guidance.
