As co-host of Boroughs & Burbs, a weekly real estate show with over one million YouTube views, I’ve spent five years tracking the high-end property markets that matter: Aspen, Palm Beach, Hilton Head, Marbella, Dubai. Co-host Roberto Cabrera and I also bring in experts: architects, economists, designers, even the governor of Connecticut.

Recently, Roberto and I were invited on the Property Profits podcast to talk about where luxury markets are headed next. Here are some of the key takeaways along with a few of our quotes from the episode.

Connecticut Moves When New York Moves

“Southern Connecticut is entirely dependent and related to New York,” I explained on the show. Buyers leave Manhattan in search of more space, better schools, and lower taxes, but they don’t leave New York behind. They relocate to Fairfield County with one foot still in the city, often keeping their job or apartment there.

That’s why tracking NYC trends isn’t optional; it’s essential. What happens in Manhattan directly influences demand in Greenwich, Darien, New Canaan, and Westport.

Why I Partnered With a Manhattan Insider

To serve buyers in Connecticut, you need to understand what they’re leaving behind in New York. That’s why I sought out Roberto. He’s one of the most knowledgeable brokers in Manhattan, and he knows how to decipher the early indicators of what’s coming to Fairfield County. “I needed to know what was going on in Manhattan to understand what’s coming to my market,” I explained. I had already been reading RobertoCabrera.com for years to anticipate where New Yorkers are in their real estate cycle. He’s been my co-host on Boroughs & Burbs since the beginning. He and I also refer business back and forth; he sends me clients looking in the suburbs, and I have sent him clients who are looking in the city.

How Manhattan’s Co-ops Drive Buyers to Connecticut

“Our marketplace is about 70% rentals and 30% purchased property,” Roberto explained. “And of that purchased property, 60% is co-ops, something most cities don’t even know much about.”

That’s a key reason buyers turn to Connecticut. Co-ops in Manhattan come with restrictions: board approvals, financing limits, use rules. By contrast, Fairfield County offers freedom, larger properties, fewer strings, and a simpler path to ownership. For many New Yorkers, that flexibility is the tipping point.

Why Foreign Buyers Are on Pause

Foreign investment has cooled, not because of pricing, but because of uncertainty. A major driver of international real estate demand is university enrollment. When families secure a spot at an elite U.S. school, they often buy nearby. But shifting visa policies have disrupted that pattern. “A big driver of foreign investment is when their kids get into U.S. universities,” I explained. “Uncertainty around visas has caused foreign buyers to hit pause.” Roberto added a telling example: “Their children got into stellar universities, but they weren’t sure they’d be able to attend, so they didn’t buy.”

NYC Is Flat. Connecticut Isn’t.

Roberto summed it up bluntly: “If you bought in 2011 and sold in 2021, you’d be at the same price… pricing went up into 2015, then came back down. We’re really flat.” Manhattan’s luxury market has been range-bound for nearly a decade. Meanwhile, Connecticut’s high-end properties have surged, driven by lifestyle migration, remote work, and buyers seeking space, privacy, and schools.

“NYC’s pricing may be stagnant,” I noted, “but Connecticut has been lifted by the exodus of buyers looking for more flexibility. They’re not just leaving the city; they’re trading up.”

When Manhattan Doesn’t Cash Flow, Investors Look Elsewhere

Even with record-high rents, Manhattan’s numbers often don’t work. “Even though rents are at all- time highs,” Roberto said, “you’d have to subsidize the investment to break even.”

That’s why many of our clients are shifting capital to markets like Dallas and South Florida, where price-to-rentnratios make more sense. “New York doesn’t pencil out right now,” I told the audience. “That’s not just an opinion; it’s what smart investors are doing.”

Newspapers, Newsletters, and 80,000 Touchpoints

In a world obsessed with social media, I still get calls from people who read my weekly newspaper column.“I’m constantly amazed by the number of baby boomers who call and say, ‘I cut your column out of the paper,’” I shared.

But print is just one piece of the funnel. Each week, I repurpose the column — along with new video and podcast content — into an email newsletter that reaches over 80,000 people. “Every Friday, I send a curated market update,” I explained, “with everything from foreign investment trends to local listings. That’s how we stay top of mind.”

The Power of Media That Actually Gets Watched

“Our property videos are not boring,” I told the audience — and the numbers back it up. Each one averages 25,000 views on YouTube alone. They’re cinematic, data-driven, and built to sell.

The Boroughs & Burbs podcast adds another 5,000 weekly listeners on Apple, with 5,000 more on YouTube

and extended via our email list. The newspaper column pulls in another 5,000. When you combine all platforms, that’s consistent, targeted exposure across print, video, and audio, designed to attract both buyers and sellers.

Whether I’m writing, recording, or walking a property, my job is to connect the dots: between markets,

between media, and between what buyers want and where they’re heading next. That’s why I watch Manhattan so closely. When things stall there, momentum often shifts to places like Fairfield County. And when foreign buyers pause, local buyers move faster. Understanding these patterns isn’t optional; it’s the edge.

Notes from the Monday Meeting

So many things that should be automatic aren’t. Cases in point: Is the asbestos remediation complete? (No, must be encapsulated.) What’s the state standard for mold? (There isn’t one.) Are there any three-month rentals? (Yes, it turns out.) Schedule the open house for 1-3 on a Sunday. (Nobody came the first hour, the second hour was packed.) Can I repair a leaking septic tank, or do I have to replace it? (still discussing). It was a reminder to me of the value of experience, team discussions, and how hard a buyer’s agent works to complete a deal.

John Engel is a broker on the Engel Team at Douglas Elliman in New Canaan, and he is caught up with the latest parlor game: monitoring sleep patterns with the Apple Watch, analyzed by ChatGPT. Core Sleep, Deep Sleep, and REM sleep: all sleeps were all called on in the writing of this column, credited with strengthening memory and recall. ChatGPT reads the watch each morning, spots the trends, and suggests how to improve each kind of sleep. But it’s not rocket science. Its recommendation: No alcohol, food or TV before bed. Read a book, AI says. Ironic, says I.

Check out John Engel’s Podcast, Boroughs & Burbs, the National Real Estate Conversation here.

Read this article on the New Canaan Sentinel website here.