A prominent Boston property developer, under a court order to sell his multi-million dollar penthouse to settle a bitter divorce, is finding no takers in a luxury market that has dramatically cooled. Jon Cronin, who helped develop the lavish St Regis Residences, is struggling to offload his personal suite, listed at $49.5 million, after six months on the market.
A Vision for a Rival Market Stalls
Boston's developers once harboured ambitions for the city's high-end property scene to compete with New York and Miami. During a pre-pandemic boom, new towers with pools, spas, and libraries saw units snapped up for record sums, with suburbanites returning to urban life. Between 2019 and 2025, around 2,500 new luxury units were added to the market, according to data, and square-foot prices soared from $1,300 a decade ago to roughly $2,200 today.
"It seemed like there was insatiable demand," Sue Hawkes, managing director of the Collaborative Companies, which worked on the St Regis, told the Wall Street Journal. However, she noted that several developers overestimated the market's depth. The pandemic triggered a sharp reversal, with residents seeking more space outside the city and collapsing demand for multi-million dollar condominiums.
The St Regis and a Cascade of Challenges
Cronin's story is emblematic of the wider sector's woes. He purchased his penthouse in the St Regis for $23.5 million in 2024, but a court has now mandated its sale amid an acrimonious split from his wife, Nicole Cronin. The 114-unit harbourfront tower, which opened in 2022, has struggled from the start. Forty-seven of its units remain unsold, and Cronin has reportedly been reluctant to discount non-waterfront homes.
His project faced a "once-in-a-generation set of disruptions," Cronin told the WSJ, citing factors beyond the market's control. These included a legal battle over waterfront access that delayed construction for four years, COVID-19, and complex building logistics. By the time the St Regis opened, the pre-pandemic sales boom was a distant memory.
A Broader Market Squeeze
The pain is not confined to one address. At the 61-story One Dalton—Boston's tallest residential building—developer Richard Friedman stated he would not start a similar luxury project in the city today. Even high-profile sales have turned sour: Dell Technologies CEO Michael Dell sold his One Dalton penthouse in August this year for less than the $34 million he paid in 2017.
Similarly, the Millennium Tower, a pioneer after the financial crisis, saw billionaire John Grayken buy its penthouse for $35 million in 2016, only to sell it in 2022. The slowdown is quantifiable: sales above $3 million in Boston plunged 35% in the second quarter of this year, leading developers to offer discounts and cover closing costs to attract buyers.
Some developers, however, resist slashing prices on premium units. "We’re not discounters," Friedman told the WSJ. Yet, Sue Hawkes estimates it would take at least 18 months to sell every Boston unit priced above $10 million. Experts point to additional headwinds, including economic uncertainty and the impact of Trump-era tariffs.
With Boston's condo sales on track for their weakest year since 2003, the glittering towers that were meant to cement its status as an ultraluxury rival now stand as monuments to a stalled ambition, leaving developers like Jon Cronin in a multi-million dollar bind.
