A Boston condo developer, compelled by his contentious divorce to sell his extravagant penthouse valued at nearly $50 million, is finding it challenging to attract buyers as the city’s real estate market faces a slump.

Jon Cronin is one of several developers who invested heavily in Boston’s condominium sector, only to encounter difficulties in selling the properties.

Cronin was instrumental in the construction of the St Regis, a stunning new tower featuring 114 residences, including his own lavish penthouse, which he acquired for $23.5 million in 2024.

Despite the allure of the development, nearly half of the units remain unclaimed, and Cronin is under mounting pressure to sell, following a recent court directive.

Amid a turbulent separation from his wife, Nicole Cronin, the developer is being compelled to liquidate assets.

He has put the penthouse on the market for $49.5 million, a sale at this price would set a new benchmark for property transactions in Boston, often referred to as The City on the Hill.

However, despite six months on the market, Cronin can’t seem to find a buyer – and he’s not the only one.  

Boston is a well-known big city and real estate developers once believed its luxury real estate market could rival New York City and Miami. 

Developer Jon Cronin, who developed the St. Regis, is having a hard time offloading his unit in the building after he was court-ordered to sell it following his divorce. Others are facing the same difficulty in the ultraluxury market 

The St. Regis sits right on the Boston Harbor, but it still has roughly a third of its units still available 

Sales on lavish new buildings with pools, spas and libraries were being snapped up by the city’s wealthiest and suburbanites were even dipping their toes back into city life. 

When luxury buildings began popping up in the Boston market, units were going for record $30million and developers believed the coastal city could truly rival its other East Coast counterparts. 

‘It seemed like there was insatiable demand,’ Sue Hawkes, managing director of the Collaborative Companies, which helped with the St. Regis, told the Wall Street Journal. 

‘Several developers had a vision that the depth of the market was higher than it is.’ 

At the height of the boom, there were roughly 1,500 new luxury units added to the market between 2013 and 2018, Collaborative Companies told the WSJ, including units in Millennium Tower. 

Eventually, that number jumped to 2,500 new luxury units between 2019 and 2025, data showed. 

As new units numbers surged, so did the price of square footage, jumping from $1,300 per-square-foot a decade ago to around $2,200 now, WSJ reported. 

 But then the pandemic hit, forcing people to flee The City on the Hill for more spacious and sanitized locations.

Millennium Tower was one of the first luxury condo buildings to emerge from the financial crisis. Billionaire John Grayken bought the penthouse for $35million in 2016, before selling in 2022

 It collapsed the luxury market in Boston, leaving developers running and landlords struggling to offload their multi-million-dollar condos. 

Cronin said a lot of the problems are out of the real estate market’s control and it forced them to ‘reshape the ultraluxury segment across Boston’. 

‘The project didn’t miss the market so much as it ran into a once-in-a-generation set of disruptions,’ he told the Wall Street Journal (WSJ).  

The St. Regis is having price-point pain. Units that did not face the water were also overpriced, with Cronin apparently refusing to offer a discount on the non-waterfront homes as many other developers do, he said in August. 

Other ultraluxury buildings are feeling a similar squeeze, such as One Dalton, the tallest residential building in Boston. The 61-story building opened in 2019.  

‘Let me put it this way, I wouldn’t want to start a new project of our size in luxury in Boston today,’ Developer Richard Friedman of Carpenter & Company, who helped create One Dalton, told the WSJ. 

One Dalton quickly attracted wealthy buyers, such as Michael Dell, the CEO of Dell Technologies, who purchased a penthouse in the building for $34million in 2017. 

Dell, who is estimated to be worth $140billion and is the 12th wealthiest person in the world, offloaded his condo in August of this year for less than he bought it for. 

‘Let me put it this way, I wouldn’t want to start a new project of our size in luxury in Boston today,’ Developer Richard Friedman of Carpenter & Company, who helped create One Dalton, told the Wall Street Journal

Millennium Tower – one of the first luxury condo buildings to emerge from the financial crisis – is in a similar crisis.

It opened in 2014 in the Downtown Crossings neighborhood and attracted buyers, such as billionaire John Grayken, who bought the penthouse for $35million in 2016. It set a record for the city, according to WSJ. Grayken later offloaded the unit in 2022. 

The St. Regis, located in the Seaport District, opened in 2019 and is located on the Boston Harbor, offering grand views of the water. But since it’s opening, it has struggled to sell units and has been delayed due to construction, the outlet reported. 

Forty-seven of the 114 units are still sitting empty, WSJ said.

Pricing has been an issue for many developers, who thought they would be able to capitalize on the soaring demand but have now been left with costly homes too expensive for most buyers.

Sales above $3million in Boston have dropped 35 percent in the second quarter, WSJ reported. Year-over-year, it has dropped 11 percent. 

This has forced developers and building owners to drop prices, offer discounts, and some are even covering the cost of closing just to get buyers into the units. 

Cronin’s St. Regis even auctioned off 10 units in the building, with five of those being snapped up by Cumberland Farms billionaire George Haseotes, who already owned five in the building. 

Buildings, like One Dalton (pictured), aren’t interested in offering lower prices, especially on its best units

One Dalton, located in the Back Bay neighborhood, is the tallest residential building in Boston, and quickly attracted Dell CEO Michael Dell, who bought a condo for $34million in 2017. He offloaded it for less than he paid for in August 

Other buildings, like One Dalton, aren’t interested in offering lower prices, especially on its best units. 

‘Those particular units are really very high up, very valuable units. We’re not discounters,’ Friedman told WSJ. 

But for Boston to sell every available unit priced above $10million, it would take at least 18 months, Hawkes told WSJ. 

Some factors that may be playing into the slowdown of the luxury market are the Donald Trump Administration’s tariffs, cuts to healthcare, and more, as Americans are feeling the strain of the US economy, WSJ reported. 

Others, like the St. Regis, missed the boom due to delays in construction and other problems. 

Construction was initially delayed on the St. Regis Residences by a legal fight with Conservation Law Foundation, which sued the Cronin Group over public access to Boston’s waterfront.

Cronin settled with the environmental group in early 2018, with commitments for additional public space and mitigation payments, the Globe reports.

But that was not the end of the developer’s woes, as he soon faced COVID-related disruptions, challenges building the massive structure on a parcel of land surrounded by water, as well as an existing apartment tower.

For Boston to sell every available unit priced above $10million, it would take at least 18 months (pictured: a unit inside the St. Regis) 

The original broker on the project, Gibson Sotheby’s International Realty, also filed and eventually settled a lawsuit against the Cronin Group in a dispute over alleged unpaid commissions, Banker & Tradesman reports.

It ultimately took four years for Cronin to complete construction on his project.

By the time the building finally opened to residents in October 2022, Cronin missed the pre-pandemic condo sales boom.

Boston’s condo sales are now on pace for its weakest year since 2003, according to data from The Collective Companies, which handles marketing for many luxury buildings in the city.

At the St. Regis Residences, sales of units priced between $2million to $3million fell 14.5 percent in the second quarter of this year, while sales of more expensive units fell 23 percent.

Sales picked up more recently, but slowed due to uncertainty around Trump’s tariffs.