Hilfiger flips Aspen home for $50 million, nets $19M in four months

Famed fashion designer sells Aspen Mountain house after paying $30.9M in December

Tommy Hilfiger sold his home at 550 Aspen Alps Road on Aspen Mountain for a $19 million profit after purchasing it in December. (Kelsey Brunner/The Aspen Times)

It didn’t take long for fashion power couple Tommy Hilfiger and Dee Ocleppo to capitalize on Aspen’s lucrative housing market, even though flipping their mansion in such quick order wasn’t part of their plan.

After paying $30.945 million for a 7,150-square-foot home located at 550 Aspen Alps Road in December, Hilfiger’s TCM1 LLC sold the same property this week for $50 million.

The deal was documented Tuesday afternoon in the Pitkin County Clerk & Recorder’s Office. The Wall Street Journal, which first reported the transaction Wednesday morning, noted the Hilfiger couple were behind the LLC that sold the ski-in, ski-out property.

“The fact of the matter is, Tommy and Dee had no intention of buying and flipping the property,” said Steven Shane of Compass in Aspen. Shane and Compass represented both the buyer and seller in the transaction. “This was going to be a legacy property for their children, their children’s children, for years to come.”

Built in 2003, the home has 7,150 square feet of livable space, seven bedrooms and eight bathrooms, according to property records. It is located just above the base of Aspen Mountain on the left side as riders go up the gondola.

“Location. Location. Location. This is Aspen’s premier ski-in/ski-out home located slope side on the Little Nell ski trail on Aspen Mountain,” said online marketing material about the property from Compass.

The deed of sale listed Silk Trail LLC as the buyer. The LLC filed what’s called a statement of foreign entity authority with the Colorado secretary of state on Feb. 15, according to public records.

One day earlier, on Feb. 14, the property went under contract, Shane said, noting a Compass colleague had alerted him about a well-heeled buyer looking for a ski-in, ski-out home in Aspen.

“I guess everything has a price, and with a limited inventory you’ve got to get creative,” Shane said. “So I asked Tommy and Dee if they would consider selling it, and they said it would have to be a very attractive price. I spoke with the buyer’s team and said we can pry this away from the existing homeowner, but it’s going to take a significant price for them to consider it. And after a couple of conversations back and forth, we agreed to a price.”

In February alone, Aspen had an inventory of 42 single-family homes for sale, a sharp decrease of 59.6% from the 104 listings in February 2021, according to data from the Aspen Board of Realtors. It’s the same story with townhomes and condos in Aspen; 14 were listed for sale in February compared to 103 in February 2021, representing a plummet of 86.4%.

The 55 real estate transactions (residential, commercial, ranch, etc.) in Pitkin County through February of this year were $559.9 million, up 23.9% over the first two months of 2021, according to a report issued Wednesday by Land Title Guarantee Co. In Aspen alone, the average single-family home sale price was $16.1 million through February, according to the report.