How ChatGPT can help you find your next house

When a $3.3 million real estate deal landed in Andy Gil’s lap, his first impulse wasn’t to speed-dial a lawyer, but to consult ChatGPT.

“I ask it questions while driving,” says the Connecticut-based investor. “I wrote the contract using AI in two hours. We just signed it today.”

Gil is part of a new wave of investors using AI as their deal-making partner, saving time, money, and sanity in the process. “I’d say ChatGPT has saved me at least six figures this year,” Gil says. “It’s like asking how much I’ve saved driving a car versus walking.”

A study by Morgan Stanley found that AI can automate 37% of tasks in the real estate industry. But since the technology is so new, “don’t expect it to work the first time,” says Liam Maher of the AI-powered comps platform Clozers. “This is the age of the tinkerer. In 10 years, everyone will have these AI superpowers at their fingertips, and in the words of The Incredibles, ‘When everyone’s super, no one will be.’ But right now, you can gain huge advantages.”

One prompt to rule them all

The first prompt every investor should try is simple: Tell ChatGPT who you are, what kind of deals you do, where you buy, and how you finance your deals. Once it understands your business, ask: “What are one or two ways I can improve or scale my current investing strategy?”

“That one prompt alone helped me rethink my operation,” says Itay Simchi, an Ohio-based investor with ProvenHouseBuyers.com. “I realized I could combine private investors with business loans instead of relying only on cash and hard money. It even gave me a social media strategy to attract private lenders, something I never would have thought to create myself.”

Simchi utilizes ChatGPT daily to underwrite and structure deals, as well as manage contractors. But it has also helped him unearth new opportunities he would never have discovered otherwise.

“A few months ago, I was negotiating with a seller who had very little equity. Selling traditionally wasn’t an option,” Simchi recalls. “Normally, I would have seen this situation as a dead end. Out of curiosity, I asked ChatGPT to help.”

The prompt: I’m buying a house in Ohio worth $185,000 with a $172,000 mortgage at 3% interest. The seller wants to walk away with $5,000. Can you help me underwrite and structure a subject-to deal that keeps payments affordable and makes sense for an investor?

Within seconds, ChatGPT delivered a detailed proposal showing that after taxes, insurance, and reserves, the house would generate a monthly cash flow of $320. “Without ChatGPT, I would have passed,” Simchi says. “But because AI helped me visualize the deal in minutes, I moved forward. It’s now a performing rental. AI didn’t just save time; it turned a dead lead into a profitable property.”

Still, not everything is a job for AI.

“It should not make decisions,” Simchi says. “It can save hours of digging, but your judgment needs to lead.”

Gil agrees, adding, “You need to think of this as a volley like in tennis, where you go back and forth. People get a couple of wrong answers, and they invalidate the entire resource instead of trying to understand how those answers were given to them. Don’t get upset; ask it how it made the mistake so you can avoid it in the future.”

Curious to learn more? Here’s more on how real estate is AI-proof and 7 ways investors can use ChatGPT.