Jay Schottenstein’s Florida Penthouse Hits Market for Nearly $34 Million

When I first heard that Jay Schottenstein had relisted his Key Biscayne penthouse, I couldn’t help but dig into who he really is—and why this home matters.

If you follow American retail even a little, you’ve probably heard his name. Schottenstein isn’t just the CEO of American Eagle Outfitters; he’s the driving force behind a suite of brands including Aerie and Todd Snyder, and part of one of Ohio’s wealthiest families.

What strikes me is how his career and personal life intersect with real estate. He’s built a reputation not only for business acumen but also for curating spaces that match his taste for privacy and luxury. While he’s offloading this Florida penthouse, he also maintains other homes in Miami and a mansion in Columbus, Ohio, showing that high-end living is a consistent theme in his life.

For anyone curious about the world of luxury real estate, understanding Schottenstein’s background gives you a lens into why this particular penthouse is more than just an expensive listing—it’s a statement.

The Penthouse Transformation — From Two Units to 13,630 Sq Ft Luxury Home

When I stepped into the story of Schottenstein’s penthouse, what really caught my eye was the scale of the transformation. Originally two separate units, he and his wife spent five years merging them into a 13,630-square-foot residence. That’s not just space—it’s a lifestyle. Every detail, from the flow of the rooms to the terraces overlooking the water, was carefully designed.

They collaborated with Geoffrey Bradfield, a designer known for sleek, beachy aesthetics, to fill the home with art and natural light. According to the Robb Report, the property now boasts about 100 feet of private beachfront, giving every room a stunning view of the ocean.

For anyone considering a luxury property, this isn’t just square footage—it’s about how the space interacts with the environment, lifestyle, and personal taste.

Much like how celebrity homes have unique design stories—such as Liberace’s legendary L.A. mansion with a piano-shaped pool—Schottenstein’s penthouse was meticulously crafted over five years to merge two units seamlessly.

Interior Highlights — Bedrooms, Bathrooms & Entertainment Spaces

Inside, the penthouse is built for both comfort and show. Four bedrooms each come with their own bathrooms, ensuring privacy for everyone. Then there are two powder rooms that double as works of art—one features a mosaic seascape, the other textured golden details.

The dining room is massive enough to seat 18, perfect for formal dinners, while the family room comes with a casual bar setup. You can whip up a tropical drink and just soak in the views, and that combination of functionality and luxury is what makes this space unique.

There’s also a stately office and closets spacious enough for anyone who loves fashion or needs serious storage.

The careful attention to interiors, from artwork placement to custom closets, reminds me of Diane Keaton’s Pinterest-inspired home where every corner tells a story of style and personality.

Outdoor & Terrace Features — Beachfront Living Redefined

Now let’s talk about the outdoors. The penthouse terraces add another 3,000 square feet of living space. You could set up lounge chairs, host dinner parties, or even place some fitness equipment, which is exactly what Schottenstein did.

Imagine working out while gazing at the ocean—that’s a lifestyle most of us can only dream of.

In addition, the home offers five parking spaces and five private storage cages. For those of us who value convenience alongside luxury, these features make the property as practical as it is beautiful.

Why Relist Now — Market Timing & Luxury Trends

One thing that stood out to me is the timing. Schottenstein first listed this penthouse in late November 2024 for $33.9 million, then pulled it off the market twice. Now he’s back with the same price, likely hoping that the winter surge in Florida’s multimillion-dollar real estate market works in his favor.

This isn’t random. Luxury properties, especially waterfront penthouses, often sell based on timing and market sentiment.

Right now, there’s renewed demand for high-end South Florida homes, which might explain why he feels the conditions are better this season. If you’ve ever watched luxury real estate, you know that patience—and timing—can make all the difference.

For real-time updates on luxury listings and exclusive market insights, some readers tune into channels where updates come straight to their devices—so you can stay ahead of trends without constantly checking multiple sites.

Luxury Real Estate Context — What This Sale Signals

This sale isn’t just about one man’s home; it’s a window into the Florida luxury market. For buyers like you, it’s a signal of what wealthy individuals are looking for: privacy, expansive terraces, beachfront access, and resort-style amenities.

Key Biscayne, where the penthouse is located, has limited inventory at this level. When a property like this comes on the market, it can set price benchmarks and influence what other sellers list nearby.

For anyone watching luxury condos in Miami or investing in high-end coastal real estate, keeping an eye on listings like this can give a sense of emerging trends and opportunities.

High-end homes in exclusive areas often see fluctuating prices, as seen recently with Richard Simmons’ Hollywood Hills home, highlighting how even celebrity properties can be influenced by market timing and demand.

Past Attempts & Why Previous Sales Didn’t Happen

If you’re wondering why this penthouse has come back to market multiple times, you’re not alone. Schottenstein first listed it in late November 2024, then removed it twice, most recently in July 2025. That’s unusual for a property of this caliber, but it highlights the challenges even high-profile sellers face.

From what I gathered, several factors likely played a role: building scaffolding, adjacent renovations, and the niche nature of ultra-luxury condos. For buyers like you, this is a reminder that expensive and exclusive doesn’t always mean “easy to sell.”

Timing, market conditions, and the very specific pool of potential buyers all matter, sometimes more than the property itself.

Potential Buyer Insights — Pros & Cons

Now, let’s think like a potential buyer. On the “pro” side, this penthouse offers privacy, sprawling terraces, beach access, designer interiors, and a layout built for both entertaining and day-to-day living. It’s a lifestyle statement as much as a home.

On the flip side, there’s the practical reality. High maintenance costs, HOA fees, insurance for a coastal property, and limited resale liquidity can all be challenges.

If you’re considering a similar purchase, due diligence is key: check the condition of the building, nearby developments, and long-term property costs. Remember, with ultra-luxury real estate, the devil is often in the details.

Hidden Considerations — Risks & Caveats

Finally, let’s talk about what you might not see at first glance. Ultra-luxury properties like this come with hidden costs: maintenance, insurance, and potential volatility in resale. The market for buyers willing and able to purchase at this level is small, so selling such a property later could take time.

Additionally, while the interiors were redesigned beautifully, it’s essential to verify updates, the building’s condition, and amenities.

Even the most stunning penthouse can have issues that only a careful inspection will reveal. For anyone serious about luxury real estate, these caveats are as important as the glamour and views.

Follow-Up — What to Watch in the Florida Luxury Market

If you’re like me and keep an eye on luxury real estate trends, this relisting is more than just a single sale—it’s a signal. Watch for the eventual sale price of Schottenstein’s penthouse; it could set a benchmark for Key Biscayne and nearby Miami properties.

Keep an eye on new listings of waterfront condos this winter. Are other ultra-luxury owners following the same timing? Changes in interest rates, insurance costs, or economic conditions can also shift demand quickly.

For anyone thinking about investing or buying a high-end Florida property, staying informed about these market signals is crucial.

Wrap-Up: Why This Penthouse Matters

At the end of the day, Schottenstein’s Florida penthouse isn’t just about celebrity or a $33.9 million price tag—it’s about understanding the luxury real estate market in context. The design, the location, the timing, and even the repeated listings tell a story about what buyers want and what it takes to sell at this level.

If you’re reading this as a potential buyer, investor, or just someone fascinated by high-end real estate, I’d encourage you to think critically: What makes a property truly valuable? And what are the practical considerations that most media outlets gloss over?

I’d love to hear your thoughts—if you were buying a waterfront penthouse like this, what would be your biggest priority: the view, the design, or the investment potential? Drop your take in the comments or let’s discuss—it’s always interesting to see how different people weigh the choices in ultra-luxury real estate.

If you’re curious about more celebrity and luxury real estate listings, check out our Real Estate & Homeownership section for the latest updates and insider insights.

Disclaimer: The information in this article is based on publicly available sources and news reports. It is intended for informational purposes only and does not constitute financial, investment, or real estate advice. Readers should conduct their own due diligence before making any decisions.