Herb Chambers spent decades building the largest privately held car dealership group in New England and sold it in 2025 in a transaction reported at $1.34 billion. His property record is unusual for someone at that level of wealth: rather than a compound, it consists mainly of high-floor condominiums in two Boston towers, a Back Bay mansion he struggled to sell, and a two-hundred-year-old house in a small Connecticut town.
The pattern is a man who moved upward within the same few blocks of Boston and then, apparently, out of the city altogether. This guide covers each property, the prices that are actually documented, and where he is reported to live now.
Herb Chambers’s properties at a glance
One Dalton, 59th floor
Four Seasons Private Residences, Boston · ~5,500 sq ft · bought 2019 for $18M
Four Seasons on Boylston Street
Three combined units, 3,363 sq ft · bought 2016 for $8,875,000 · listed April 2022 at $18M
Back Bay mansion
Beaux-Arts, Boston · listed at $14.9M, reduced to $10.5M
Old Lyme, Connecticut
Built 1820 · 4,100+ sq ft on 3.25 acres · purchase not documented
Who is Herb Chambers?
Herb Chambers is an American businessman who built The Herb Chambers Companies into New England’s largest private automotive retail group. In February 2025 he agreed to sell the business to Asbury Automotive Group, and the transaction completed in July 2025. It covered 33 dealerships, 52 franchises and three collision centres, representing about $2.9 billion of revenue in 2024, at an aggregate net purchase price reported at around $1.45 billion against a headline figure of $1.34 billion.
He did not exit entirely. He stayed on as a special adviser to Asbury and retained ownership of one dealership, Mercedes-Benz of Boston in Somerville. He is also known for owning the superyacht Excellence.
That 2025 sale is the backdrop to everything below: a man in his eighties converting an operating business into liquid wealth, while simultaneously trying to sell two Boston properties.
The Boston condominiums
Chambers bought into the Four Seasons on Boylston Street in 2016, paying $8,875,000 for three continuous units combined into a single residence of 3,363 square feet, with three bedrooms, three and a half bathrooms and a study.
Three years later he moved up rather than out. In 2019 he paid $18 million for a condominium at the Four Seasons Private Residences at One Dalton Street, the tall tower that had just been completed a short distance away, taking roughly 5,500 square feet on the 59th floor. One Dalton is among the most expensive residential buildings in Boston, and a 59th-floor unit in it is about as high as private residential living goes in the city.
Having moved into the Dalton apartment, he put the Boylston Street residence on the market in April 2022, asking $18 million, precisely what he had paid for the new one and more than double what he had paid for the old one six years earlier.
It did not go well. The property was widely reported as slow to sell, with price reductions following. That is a useful reality check: a doubling of an asking price over six years is an aspiration, not a valuation, and Boston’s ultra-prime condominium market is small enough that a handful of unsold units matters.
The Back Bay mansion
He has also been trying to sell a Beaux-Arts mansion in the Back Bay, on Commonwealth Avenue, one of the grandest residential streets in the city.
The pricing history there tells the same story more starkly. The asking price fell from $14.9 million to $10.5 million across successive reductions, a cut of roughly 30 per cent. Large period townhouses in the Back Bay are architecturally magnificent and commercially awkward: expensive to run, difficult to modernise under conservation constraints, and appealing to a very narrow set of buyers.
$4.4M
↓ about 30%$14.9M → $10.5M
About $4.4 million, or roughly 30%, taken off the Back Bay asking price: first ask $14.9M, latest ask $10.5M.
Boston’s high-end market has absorbed plenty of executive money over the years, as the account of Paul Edgerley’s Brookline estate shows, but the top of it moves slowly.
Where does Herb Chambers live now?
Reporting places him in Old Lyme, Connecticut, in a house built in 1820, with his partner.
The property is described as having three bedrooms and four bathrooms across more than 4,100 square feet, on 3.25 acres, with a helicopter landing pad on the grounds. The helipad is the detail that makes practical sense of the arrangement: Old Lyme sits on the Connecticut shoreline roughly two hours from Boston by road, and a helicopter reduces that to a short hop, which for someone still advising a national dealership group and retaining a Boston dealership is the difference between commuting and not.
Two qualifications. This account comes from specialist coverage rather than from a property record, so it is reported rather than documented, and no purchase price or date for the Connecticut house has been published. And he has not disposed of his Boston property: the One Dalton condominium remains his, and both the Boylston Street residence and the Back Bay mansion were still being marketed rather than sold at the time of the most recent reporting reviewed here.
The most accurate summary is that Chambers keeps a Boston base in one of the city’s tallest residential towers, has been trying for several years to shed two other Boston properties, and is reported to live principally at a historic house in Connecticut. Billionaires commonly hold a working city residence alongside a quieter primary home, a pattern visible in the property record of Kenneth Griffin at a considerably larger scale.
Sources
- Boston.com on the April 2022 listing at $18 million, the 2016 purchase at $8,875,000 and the property’s configuration.
- CommonWealth Beacon on the 2019 purchase of the One Dalton condominium for $18 million.
- CBS Boston and Asbury Automotive Group on the 2025 sale, its value, scope and completion.
- SuperYachtFan on his reported Old Lyme residence and the property’s description.
