Josh Flagg doesn't just buy houses; he collects legacies. If you've followed the Million Dollar Listing Los Angeles star for more than five minutes, you know he has a thing for history, old-school Hollywood glamour, and properties that make most people’s bank accounts weep. But lately, the buzz around the Josh Flagg new house situation has been a little confusing. Is he still gutting that 1920s mansion on North Bedford Drive? Did he actually move into Charlie Puth’s old place? And what’s this about a $9 million "summer cottage" in the Hamptons?
Honestly, keeping track of Flagg’s personal real estate portfolio is a full-time job.
The Trousdale Estates Pivot
The biggest recent shift in Flagg’s living situation happened when he officially pivoted toward Trousdale Estates. For years, he was obsessed with the "Flats" of Beverly Hills. He even bought his "childhood dream home" on North Bedford Drive back in 2022 for about $9.2 million. But that project turned into a bit of a nightmare. He famously stripped it to the studs, fired multiple contractors, and realized that living in a construction zone—or waiting years for one to finish—wasn't exactly the vibe.
So, he went off-market. He ended up snagging a mid-century modern masterpiece in Trousdale Estates for roughly $14 million. This is the Josh Flagg new house that everyone is talking about right now. It’s not just any house; it’s a 1965 Rex Lotery design.
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If you’re a fan of the show, you know Flagg usually leans toward traditional, "grandma-chic" aesthetics. This move to a sleek, glass-walled mid-century pad was a curveball. But the history sold him. The house was previously owned by singer Charlie Puth, and way before that, it belonged to Tonight Show producer Freddy de Cordova. It’s even rumored to have hosted Ronald Reagan’s "kitchen cabinet" back in the day.
What’s Inside the Beverly Hills Retreat?
The house is about 4,500 square feet, which is actually somewhat "modest" by Beverly Hills billionaire standards, but the architecture is the star. It has four bedrooms and four bathrooms, but it’s the flow that matters.
- The View: Trousdale is known for being "on a crest," and this property delivers panoramic views of the Los Angeles skyline.
- The Renovation: Flagg teamed up with celebrity designer Jake Arnold to refresh the space. They aren't tearing it down—thank God—but they are tweaking it. Flagg has mentioned wanting to enclose certain outdoor areas to add about 1,200 square feet of interior space.
- The Vibe: Think brutalist stone walls, floor-to-ceiling glass, and a pool area that feels like a 1960s film set.
The Surprise Hamptons Expansion
Just when everyone thought he was settled in the hills, Flagg decided he needed a 3,000-mile commute. In August 2025, he closed on a $9.2 million home in East Hampton. Specifically, it’s in the Georgica Estate section, which is basically the "Old Money" corner of the world.
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This isn't a dusty historic renovation. It’s a brand-new 2024 build. It’s got six bedrooms, a heated saltwater pool, and a pool house with a gym. He bought it with a childhood friend, Justin Gruenberg, mostly because he’s been spending a ton of time in New York lately. Apparently, being the king of 90210 wasn't enough; he wanted a piece of the East Coast summer scene too.
Why the Bedford Drive Mansion is Still a Thing
You might be wondering: "Wait, did he sell the Bedford house?"
Nope. As of early 2026, Flagg still owns the North Bedford Drive estate. He’s admitted that buying it might not have been his "most intelligent" move financially, given the massive renovation costs (estimated at another $7 million), but he’s stubborn about his favorites. He’s basically using the Trousdale house as his primary residence while the Bedford project slowly moves forward. It’s a classic real estate mogul move: buy the dream, realize the dream is a headache, and buy a second dream to live in while you fix the first one.
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The Real Cost of Being Josh Flagg
When you add it all up, Flagg is sitting on tens of millions of dollars in personal residential real estate. Most agents just sell the lifestyle; he actually lives it. Between the $14 million Trousdale pad, the $9 million North Bedford project, and the $9 million Hamptons house, he’s heavily leveraged into the luxury market.
Is it a risk? Sure. But Flagg has always operated on the "buy what you love" principle. He’s bet on the fact that these iconic zip codes rarely lose value in the long run.
Actionable Insights for Luxury Real Estate Enthusiasts
If you’re looking to follow the "Flagg Method" for your own property search or just want to understand the market better, keep these points in mind:
- Prioritize Pedigree: Flagg buys homes with a "story" (architects like Rex Lotery or famous former owners). Pedigree preserves value even when the market dips.
- Off-Market is King: His best deals, including the Charlie Puth house, happened behind closed doors. If you want the best stuff, you have to find it before it hits the MLS.
- Renovation Reality Check: Even the world’s top agents get overwhelmed by renovations. If you're buying a fixer-upper, have a "Plan B" living situation ready.
- Location Diversification: Moving into different markets (like the Hamptons) can be a smart play if your business or lifestyle is shifting geographically.
If you are tracking the Josh Flagg new house updates to see where he lands next, keep an eye on his Instagram or Million Dollar Listing. He’s rarely in one place for long, and with his recent move to Compass, his portfolio is only getting more complex.