J
ay Schottenstein, chief executive of American Eagle, is putting his Key Biscayne penthouse on the market for $33.9 million. The property, represented by Julian Johnston and Jonathan Lifschutz of Corcoran, marks the third attempt to sell the home within a year. The listing first appeared late last year and was re‑introduced earlier this year at the same price.

    The 10,000‑square‑foot penthouse was created by merging two top‑floor units, giving residents more than 10,000 sq ft of interior space plus an additional 3,000 sq ft of oceanfront terraces. In 2017, designer Geoffrey Bradfield refreshed the interiors. The building itself was still under scaffolding when the first two listings went live, and the neighboring Ritz‑Carlton’s $100 million renovation was incomplete, according to Johnston.

    Key Biscayne is a 1.2‑square‑mile barrier island across Biscayne Bay from Miami. With just over 14,800 residents (2020 census) and two nature parks flanking the town, it offers a high degree of privacy. Despite its small size, the island commands premium prices; Redfin reported a median sales price of $2.32 million in October based on 14 homes sold. The penthouse boasts western Miami views, a chef’s kitchen, a large dining area, a gallery‑style hallway, and a bathroom with mosaic tile. Four ensuite bedrooms, an executive office, staff quarters, and ample parking complete the layout. The closets are described as “couture‑level,” a nod to Schottenstein’s flagship brand.

    Schottenstein bought the property in 2006 for $5 million. He has overseen American Eagle since 2005 and also chairs DSW. His family’s Value City Furniture, based in Columbus, Ohio, filed for Chapter 11 a few weeks ago amid macroeconomic pressures, and the company is now up for sale with plans to cut more than 300 jobs.

    The penthouse’s marketing highlights its suitability for a global fashion magnate, a claim that echoes recent headlines. American Eagle’s stock rose up to 4 % last week after announcing that Martha Stewart would replace Sydney Sweeney as the face of its “good jeans” campaign, following a divisive debate over the former star. Schottenstein told the Wall Street Journal that the company stands behind its creative choices.

    Schottenstein relocated to a Miami Beach penthouse a few years ago to be closer to family, but he is now looking to sell the Key Biscayne property. The listing’s current price remains unchanged from its first appearance, and Johnston attributes the repeated attempts to market timing rather than the property itself.