Pick or Pass: This $8.95 million Boston penthouse awaits a buyer to call it home

By Chloe Adams

October 15, 2023

With floor-to-ceiling windows, 2,725 square feet of outdoor space, a balcony in all three bedrooms and room service from a French-Mediterranean restaurant inside the building, the $8.95 million unit, also known as the “penthouse in the sky,” is a grandeur living space that borders Boston’s South End and Back Bay.

The two-story penthouse, sitting at the highest level of 221 Columbus Ave., saw a $1 million decrease since being sold for $9.95 million last month — an adjustment that highlights challenges for the multi-million dollar space to be of serious interest to potential buyers.

One of the penthouse’s listing agents, Colleen Coopersmith, a realtor from Cort Petrocelli Coopersmith, said she has been unable to find “the right buyer.”

At an estimated monthly cost of $63,689, the penthouse has been waiting to secure a deal since June.

Coopersmith said it has a unique “wow factor” that is not commonly found in the city.

“There’s nothing cookie cutter about it... There’s one button — I’ve never seen this before — it’s for all the lights to go on as you first walk in on the whole first floor,” she said. “I think the fact that it’s modern with all the lights and all the windows is just spectacular.”

Depending on what someone is looking for, Coopersmith said the unit’s features are able to fulfill a variety of different needs.

“The buyer could be an empty nester, couple or single that needs two offices or three bedrooms... A family could work in it too because you have three good-sized bedrooms,” she said.

Jim Black, owner of the Jim Black Group, a real estate firm that serves clients in Massachusetts, said realtors must think outside the box when selling higher priced homes.

In those cases, realtors “try to truly identify who is the correct client to buy that home, as opposed to marketing to the masses, and we may need to personally reach out to specific buyers who would be a good fit,” said Black.

The penthouse, located in the Albert Pope Building, was originally a bicycle factory built in 1880. By 1998, it was redeveloped into a condominium complex, according to real estate agency Campion and Company. Coopersmith said the man who redeveloped the building created the penthouse for himself to live in.

Seth Greenberg, co-owner of Mistral restaurant on the building’s first floor, said this redeveloper happens to be his business partner Paul Roiff — the two Boston University alums collaborated to form the fine dining establishment back in 1997.

Greenberg, dubbed the “nightlife king” by Boston Magazine in 2009, said he wanted the restaurant to revive this part of the city and bring a high-end spot to Bostonians.

“The truth is, 25 years ago, it was a little sleepy over there,” said Greenberg. He said the business took off right away due to “so much anticipation when we first opened — there were lines out the door.”

Mistral’s highest priced menu item goes for $98: the dish includes a roast rack of Colorado lamb, dauphinoise potatoes, honey roasted carrots and haricot verts.

All along, Greenberg said the plan was to open a five-star restaurant and have that be the selling point of what would motivate people into purchasing the condos.

While he said the restaurant is currently doing better than ever, the penthouse still awaits a buyer to lock in a deal.

Of the building’s advantages — like providing a full-service concierge center, open views and a parking garage — Greenberg said, aside from a tenant, something else is missing.

“It’s more of a chic loft-style, but yeah, there’s no gym,” he said.