Name: Top Real Estate Editors Discuss Chicago's Value Play, Portal Wars & Political Crosswinds for 2026
Uploaded: 2026-07-15T12:00:34Z
Description: Is Chicago the most underrated value play in U.S. real estate right now?

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Is Chicago the most underrated value play in U.S. real estate right now?

Top Real Estate Editors Discuss Chicago's Value Play, Portal Wars & Political Crosswinds for 2026

Compass spent years building the largest residential brokerage in America. Now it's defending that position on multiple fronts.

Why Everyone Is Coming After Compass

What separates successful developers from everyone else? GFP Real Estate’s Brian Steinwurtzel says it comes down to one thing: leaning in when others run.

This one thing makes a developer successful, says GFP Development CEO

Manhattan's housing market has spent the last decade doing something few major U.S. markets can claim: staying remarkably stable.

Manhattan home prices have been frozen for a decade. Here's why.

President Trump says he won't sign Congress's bipartisan housing package, calling it "a big yawn." But at midnight, the legislation is still poised to become law.

Trump won't sign this housing bill. It may become law anyway.

OneRepublic's Ryan Tedder isn’t just writing hit songs — he’s quietly built a serious real estate portfolio.

OneRepublic's Ryan Tedder: Why I Pull All My Music Money Into Real Estate

Has the Sun Belt peaked? JPMorgan weighs in

The final World Trade Center tower is finally happening.

The last piece of World Trade Center is finally rising

Is the American mall back?

Michael Gross has spent decades proving that luxury real estate is never just about the view.

How 15 Central Park West changed luxury real estate forever

New York City's largest office-to-residential conversion came to an abrupt halt Tuesday.

Collapse fears at NYC biggest conversion

Would New York's pied-à-terre tax work in practice?

The hidden cost of New York's pied-à-terre tax

In the latest TRD Roundtable, made possible by Amazon Key, The Real Deal editor-in-chief Stuart Elliott leads a candid conversation with top operators, asset managers, and owners about what’s really happening in multifamily—from New York’s regulatory crunch to Sun Belt growth and AI-driven building operations.

Inside the Multifamily Squeeze: Political Risk, AI & Operations in 2026 | TRD Roundtable

What turns an obscure island into the world's most coveted billionaire address?

How St. Barts became a billionaire playground

For years, Wall Street was cast as the housing market's ultimate villain. The latest data tells a more complicated story.

Wall Street Is Pulling Back From Housing. Here's Why.

Billionaire villas, Russian oligarchs, drug smugglers, superyachts, and a tiny Caribbean island trying not to lose its soul.

The Secret Real Estate Power Game in St. Barts | Coffee Talk with Michael Gross

The loudest real estate fight inside NYC’s $125.8B budget wasn’t over towers or taxes. It was over who gets help paying rent — and who picks up the tab.

NYC’s $1.8B housing voucher fight, explained

If Mayor Mamdani called you today, how would YOU fix New York’s housing crisis?

"Mayor Mamdani calls: What's your plan to fix NYC housing?" | Victor Sigoura answers

New York is about to tax second homes. But who actually pays, and how does the city plans to enforce it? Well, that's still being figured out.

NYC's New Pied-à-Terre Tax Explained

Kanye West's gutted Malibu mansion was just the beginning. The Tadao Ando-designed home is now at the center of bankruptcy, foreclosure and a previously unreported SEC investigation, exposing how one of Malibu's most coveted properties became a cautionary tale about leverage and speculative investing.