Rosie O’Donnell’s Old Miami Beach Mansion Sells for $36 Million

When I first read that Rosie O’Donnell’s old Star Island mansion finally sold, what stood out wasn’t just the $36 million price tag. It was the story behind the number.

Here’s the thing: this house has been through a wild ride. Rosie bought it back in 1999 for about $6.7 million—pocket change compared to today’s market. She let it go in 2003 for $16.5 million, and the Frankels, who owned it after her, poured years of renovations into the property.

Fast forward to late 2024, they listed it for a jaw-dropping $54 million, hoping to cash in on Miami’s luxury frenzy. The problem? The market had cooled a bit. Even in a billionaire playground like Star Island, buyers aren’t writing blank checks anymore.

That’s where Russell Weiner, the billionaire founder of Rockstar Energy, comes in. He swooped in at $36 million, which is nearly $20 million above what the Frankels originally paid Rosie, but still a hefty discount compared to their dream number.

If you zoom out, the deal tells two stories at once: luxury real estate still appreciates massively over time, but sellers can’t always dictate the market.

For me, that’s the hook. When you hear about these celebrity homes, it’s tempting to just gawk at the price. But if you look closer, this sale shows how even the most glamorous properties have to bow to real market forces.

What do you think—was this a smart buy at $36M, or do you feel the Frankels left millions on the table?

Inside the Mansion: What $36M Buys on Star Island

I’ll be honest with you—reading about this house feels like flipping through a glossy Robb Report feature. And in fact, Robb Report covered it in detail when the listing hit the market. The property isn’t just big, it’s cinematic.

Built in the 1920s, it carries that old Miami Mediterranean vibe: arched doorways, sunlit courtyards, and the kind of detailing you don’t see in new glass towers.

Step inside and you’ve got over 11,000 square feet across the main home plus two guesthouses. Eight bedrooms, eleven bathrooms, and all the extras you’d expect at this level. Outside? A bean-shaped pool with a slide, a motor court wrapped in banyan trees, and a private dock that can hoist a serious yacht. It’s the kind of place that screams “arrive in style, leave on a boat.”

The interiors mix warmth and luxury—French doors that spill onto a veranda, a dining room built for long dinners, and a kitchen decked out with Viking and Sub-Zero gear. This isn’t some sterile billionaire bunker. It’s lived-in luxury, the kind of house where old money and new money would both feel at home.

If you love exploring legendary celebrity estates, you might also enjoy seeing how Christopher Lloyd puts his Santa Barbara pad on the market for $6.3 million.

Planned Upgrades by Russell Weiner

Now here’s where it gets interesting. According to Realtor, Russell Weiner isn’t just buying the house—he’s re-imagining it. He’s planning to expand the place to nearly 15,000 square feet and add what every billionaire seems to want right now: a spa, a gym, a cabana, even a padel court.

That detail matters because it shows how these trophy homes aren’t static. Each owner leaves a stamp. Rosie had her quirks, the Frankels modernized it, and now Weiner is pushing it into ultra-resort territory.

If you ask me, that’s the real flex: not just owning a piece of Star Island history, but shaping it into your own private paradise.

Similar to Rosie’s move abroad, Roseanne Barr’s Hawaii ranch recently hit the market at $1.95 million, offering a glimpse into how celebrity lifestyles influence real estate choices.

Star Island: America’s Billionaire Playground

If you’re not from Miami, it’s easy to hear “Star Island” and think it’s just branding. But no, it’s exactly what it sounds like: an enclave where billionaires and celebrities share fences.

Right now, you’ve got hedge fund titan Ken Griffin quietly assembling over $169 million worth of land there. The Estefans have long been fixtures. Rick Ross and Diddy have called it home. And earlier this year, developer Vlad Doronin sold Shaquille O’Neal’s former estate for an eye-popping $120 million.

That’s the context around Rosie’s old house. $36 million sounds like Monopoly money to most of us, but on Star Island, it’s almost mid-range. The real draw isn’t just the house—it’s the gates, the privacy, and the status that comes with saying “I live on Star Island.”

Waterfront luxury isn’t limited to Miami—Neil Giraldo and Pat Benatar’s former oceanfront Hawaii home recently went on sale for $5 million, showing that celebrities around the world favor prime waterside locations.

Rosie O’Donnell: Life After Miami Mansion

Rosie herself has moved far from Biscayne Bay. In fact, she’s been pretty open about leaving the U.S. political climate behind and relocating to Ireland with her child Clay. And just earlier this year, she finally sold her Midtown Manhattan penthouse for around $7 million after struggling to find a buyer.

I think it’s important to add this here because a lot of readers click these stories for the celebrity angle, not just the real estate. Rosie’s life has shifted dramatically since those Miami days. Back then, she was a TV mainstay with a splashy mansion.

Today, she’s chasing a quieter, more grounded life abroad. That contrast makes this sale hit differently—it’s not just about the house, it’s about how time moves on for everyone, even celebrities.

I often get quick updates on properties like this on WhatsApp—if you like following these stories as they break, you might enjoy the regular updates I share there.

The Bigger Picture: Miami’s Luxury Market Trends

So what do we take away from this sale beyond the celebrity name? Miami’s luxury market is hot, but it’s also showing its cracks. The Frankels tried for $54 million and had to cut down to \$36 million. That’s a huge discount, even though they still walked away with a massive profit.

For buyers, that signals opportunity. If billionaires are negotiating 30–40% discounts off ask, you know sellers are adjusting expectations. For sellers, it’s a reminder: even if your property has history and location, pricing still matters.

Compared to Los Angeles or New York, Miami still looks like a relative bargain at the very top end. $36 million here buys you water frontage, privacy, and celebrity neighbors. In Beverly Hills or Tribeca, that money might only get you half the square footage.

At the end of the day, Rosie’s former mansion is more than just a house. It’s a case study in how celebrity culture, real estate strategy, and market timing all collide.

What’s your take—do you see Miami’s luxury market cooling down, or is this just a temporary pause before the next wave of record-breaking sales?

Key Takeaways for Readers

Looking at Rosie O’Donnell’s former Miami mansion sale, a few things become clear. First, celebrity history adds undeniable allure, but it doesn’t guarantee top-dollar if the market isn’t aligned. Second, Star Island remains one of the most exclusive enclaves in America—privacy, water frontage, and the company you keep matter as much as the house itself.

Third, even in ultra-luxury real estate, timing is everything. The Frankels made a solid profit, but the difference between their asking price and the final sale shows how the market can humble even the wealthiest sellers.

And finally, for buyers like Russell Weiner, it’s about more than just owning a home—it’s shaping it into a personal luxury retreat that reflects status, lifestyle, and long-term investment.

For me, the story isn’t just about a $36 million sale. It’s a lens into the rhythm of Miami’s high-end market, the cultural weight of celebrity homes, and how every owner leaves a mark on these legendary estates.

So, tell me—if you had the chance to live on Star Island, would you buy a historic celebrity mansion, or would you rather build your own from scratch?

If you’re curious about more celebrity homes and luxury real estate trends, check out our Real Estate & Homeownership section for the latest stories.

Disclaimer: The information in this article is based on publicly available sources and is intended for informational purposes only. Prices, ownership details, and plans are subject to change and may not reflect the most current data. This content does not constitute financial or real estate advice.