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.

Housing still hasn’t recovered from Covid. Only 17 states, mostly in the South, now have more homes for sale than they did in 2019. Meanwhile, Northeast and Midwest markets remain stubbornly undersupplied, and four states have less than half the inventory they had six years ago. Find out why, and how this impacts prices.

First-time homebuyers are how old? The median age of first-time homebuyers rose from 28 back in 1992 to a record high of 40 in 2025, according to the National Association of Realtors. And that’s not all that’s changed for home shoppers.

New York City’s next mayor: Zohran Mamdani won NYC’s mayoral race—here’s what this means for real estate in the Big Apple and beyond.

🫣 A risky loan returns. Adjustable-rate mortgages made up 10% of loan applications in the week ending October 3, the highest share since 2023, according to the Mortgage Bankers Association. But this gamble might not be so dicey today.

Won a bidding war? One study of 14 million home sales over two decades found that winning a bidding war isn’t worth it.

The REIT awards: Hoya Capital’s REIT scorecard tallied up which real estate sectors are flourishing and fumbling so far this year, and it’s full of surprises. See the full REIT scorecard here.

🛒 Follow the Walmarts? This big-box chain plans to open over 150 new stores nationwide over the next few years. And investors are tracking where these stores are going up for good reason.

🫨 Townhouse on a diet: Only 9.5 feet wide, this slim dwelling was just listed for a shockingly fat price: $4.195 million. Will buyers bite? Take a look inside.

When developer Robert Kaliner found out the townhouse next to his renovation was for sale, he didn’t hesitate: He combined the two into a single 40-foot-wide megamansion.

RoundSquare Builders paid just over $18 million for the side-by-side properties—one once home to John Lennon, the other to composer John Cage—and after three and a half years of work, it will soon hit the market for a casual $75 million (listed by Matt Lesser at Leslie Garfield). If it sells for that price, it would set a record for a downtown Manhattan townhouse. Here’s how this epic renovation came together.

Q: Why did you decide to turn two townhouses into one? “Simple answer: These kinds of opportunities—a double-wide in a prime New York location—are unicorns. It was a gift, and we wanted to maximize that opportunity.”

Q: What were the main challenges? “You never know what the Landmarks Preservation Commission is going to approve. First, we wanted the houses to look identical at the top. Landmarks had us make them look a little bit different. In hindsight, they did us a favor. It’s a perfect mix of looking like one but a little bit not like one. It’s the perfect balance.”

Q: What challenges did you face in the interior? “Removing the party wall, the structural boundary between the properties. This required more steel for structural support than you could imagine. If you don’t use the best engineers you know, this is why you hear all the time of buildings cracking or coming down.”

Q: Did you preserve anything from the days when John Lennon and Yoko Ono lived there? “John Lennon’s spiral staircase was a no-brainer.”

Q: Why did you decide to keep the house under wraps during renovation? “It was not a stunt, like a restaurant opening that’s hard to get into. It’s because people don’t like looking at a house in the throes of construction. You just want to bring your toothbrush and move in.”

Q: Do you think it will sell for the full $75 million? “Comparable properties sold quickly with bidding wars, but the goal isn’t record-breaking. It’s ensuring the buyer loves the house.”

Click here to see more photos of this epic property.

“Good bones” is a cliché trotted out for homes that don’t wow at first glance. Think shag carpet from the ’70s…followed by someone saying, “But look at this home’s good bones!” Still, what does that really mean?

“The term gets bandied about a lot, but it has a concrete meaning in real estate and construction about the basic integrity of the building,” says Jacob Naig, a real estate investor based in Des Moines, IA. “I’ve been in houses with dated surfaces but straight framing, dry basements, and decades left on the roof. That’s good bones.”

These solid-but-scruffy properties tend to be structurally sound investments since they may require only a few cosmetic updates rather than a whole new foundation or roof. In fact, these fixer-uppers tend to sell for half the price of a typical home, according to Realtor.com.

Still, just because someone says a home has good bones doesn’t mean it’s true. Keep your eye out for doors that stick, cracks in the walls or foundation, or place a marble on the floor to see if it slopes. All can be signs that these “good bones” are just wishful thinking. Here’s more on where you can find unbeautiful bargains for as little as $66,750.