Hilfiger Nets $19M on Slopeside Aspen Home in Four Months

Tommy Hilfiger and his family had spent years looking for the perfect legacy piece in Aspen. 

Hilfiger and his wife Dee Ocleppo  finally found — with the help of their realtor, Steven Shane of Compass in Aspen — the perfect home that would accommodate multiple generations of Hilfigers.

Shane swears that the couple’s purchase of 550 Aspen Alps Road, which the Hilfiger family closed on in December 2021, was intended as a long-term investment. But months after purchasing what was intended to be their legacy property, the Hilfigers — on Feb. 14, Valentine’s Day — had the 7,150-square-foot residence under contract, Shane said.

They sold it for almost $20 million more than they’d paid for it.

“I’ve been working with Tommy and Dee for about five years trying to identify the perfect property for them and for their children and their children’s children,” Shane said. “And finally, we found this property. It was listed for $35 million … we paid [almost $31 million].”

But when a colleague at Compass introduced Shane to another buyer — he had to sign a nondisclosure agreement in the business relationship and so did not reveal the identity — the realtor came to realize that the Hilfigers’ new residence was the perfect fit.

“When I understood the buyer’s criteria and his affinity to ski access, I swallowed hard and called Tommy and said, ‘Hey look, I’m not here to ruin your dream, but I have somebody who I think is the right fit for the home you just bought,’” Shane recalled. And the Hilfigers told him that for the right price, they would sell. On Tuesday, they closed for roughly $50 million without the property ever being listed.

Shane acknowledged that when real-estate inventory is as in demand as it is in Aspen but with such low inventory, industry professionals have to get “creative.”

“A lot of the deals that I am doing are unlisted properties,” he said. “There are sellers out there that have aspirational asking prices; they understand what’s happening in the market. But the fact of the matter is we have a finite amount of inventory in Aspen — we don’t have any developable land. So we establish new baselines every day, new pricing per square foot.”

He went on to explain that the Aspen community represents a tangible investment for purchasers that offers real quality-of-life returns. And so long as that is the case, he doesn’t see the local real-estate market slowing down. The COVID-19 pandemic sparked a momentum that is downright existential in nature — people previously “on the sidelines” decided that, with remote work becoming the new norm, it was time for a change in locale and made the proverbial leap into buying in Aspen. 

“The only thing that I can see slowing this down — it’s not interest rates — but I see potentially slowing things down is when pricing in Aspen reaches a level where … if in fact the buyer is exclusively coming here to ski, then they could go to the Sun Valley, a Telluride, even a Vail, where the pricing is less expensive,” Shane said. “But most people that come here are coming here to enjoy all four seasons and the culture that Aspen has to offer.”

As for the Hilfigers, they intend to maintain an 81611 address. 

“We’ve discussed a handful of properties. I would love to see Dee and Tommy buy something that could make an iconic Hilfiger estate,” Shane said. “They have impeccable taste, and I envision them buying something in an A+ location that might require some remodeling and refurnishing where they can add value.”

The fashion power couple hadn’t had time to make such renovations on their newly acquired slopeside home, which boasted seven bedrooms and eight bathrooms.

“They [were] selling this house exactly the way they found it,” Shane said. “I think that when you have a ski-in, ski-out Aspen Mountain property — or for that matter an ocean-front Palm Beach property — the pricing-per-square-foot analysis no longer applies. And I feel like the buyer, believe it or not, in a short amount of time will consider this a good deal.”

By: Megan Tackett I  Aspen Daily News I March 24, 2022