Harvey Weinstein’s Former Connecticut Mansion Razed, Bare Land Listed at $21 Million

With his once high-flying life in penurious, imprisoned shambles, the former Connecticut “Gold Coast” mansion of disgraced former Hollywood super-producer Harvey Weinstein has been demolished, and the prime waterfront acreage recently put up for sale with a $21 million asking price. Spanning a total of 5.66 acres, the former Weinstein estate comprises two separate parcels along one of Westport’s most exclusive and expensive streets. The larger 3.03-acre plot is priced separately at $11 million, while the smaller 2.63-acre parcel has a $10 million hang tag.

Once one of Tinseltown’s most powerful, prolific, and infamously imperious power players, Weinstein was sentenced to 39 years in prison on multiple charges of rape and sexual assault, first in New York in 2020 and then again last year in California.

Now 71, the Miramax co-founder sold the two parcels that form his former Westport spread for $16 million in 2018, just as his spectacular fall from grace and serious legal issues went into overdrive. Though proceeds likely went to pay his high-priced army of criminal and civil defense attorneys, on paper, Weinstein made out like a bandit on the sale. He acquired the two properties in two transactions, the first in 1994 and the second in 2000, for a total of $8.24 million. He and his second-ex wife, red carpet fashion designer Georgina Chapman, held their wedding on the property and some years later hosted fundraising events for Barak Obama’s 2012 re-election campaign.

The buyers, English commodities trader turned graphic designer Andrew Bentley and art historian Fiona Garland, soon sent the wrecking ball through Weinstein’s traditional mansion. Gone is the nearly 9,000-square-foot early 20th-century Colonial and gone is the adjacent, barn-style guest house. Also gone is the swimming pool that sculptured gardens once surrounded. There were also two smaller homes on the property that have been demolished. Still in place are the properties’ rare geography: 550 feet of water frontage — each parcel spans 277 feet along the water — and distant views of the Manhattan skyline over the Sound’s dark, glistening waters.

Whatever ideas and plans Bentley and Garland may have had to develop the property, which anchors the west end of a leafy two-lane street that parallels a stretch of the Long Island Sound, have now been set aside. Still, the couple were residents of the seaside neighborhood long before they bought the old Weinstein estate. They preside over a vast estate at the opposite eastern terminus of the long street, part of which was acquired in 2006 for $25 million from Marlo Thomas and Phil Donahue. Surrounded by acres of rolling lawn, the park-like property includes a shingled mansion, an octagonal entertainment pavilion, a tennis court, and a classic red barn. Cleverly designed by architect Roger Ferris to disappear into the landscape beneath a grassy knoll, there’s also a minimalist pool house.

Other homeowners along the hallowed lane include a baseball team’s worth of private equity tycoons and an American oil heiress whose two of three marriages were to European royalty.

Around the same time Weinstein sold the Westport estate, he took a significant loss on the $10 million sale of a waterfront mansion in the Hamptons he bought just 3.5 years earlier for $11.4 million. He more than made up for the loss with a plush Manhattan townhouse that was picked up in 2006 for almost $15 million and sold in 2018 for nearly $26 million.