A haven for hedge-fund titans and Hollywood grandees, Greenwich is one of the world’s most expensive residential enclaves, where eye-watering prices meet unapologetic grandeur.
4 min
Greenwich, Connecticut, is in New England (just barely), but that doesn’t mean it’s a quaint, sleepy small town with covered bridges and white churches on the green.
It’s leafy, certainly, but it’s also a luxury-minded power centre close to New York City, with many celebrity residents (director Ron Howard, singer Diana Ross, actor Meryl Streep and, at one time, Australia’s own Mel Gibson).
The main shopping street, Greenwich Avenue, is home to brand stores such as Hermès, Kate Spade, Saks Fifth Avenue, and Tiffany & Co.
And Greenwich, particularly in the “back country” north of the Merritt Parkway, is host to some of the most exclusive real estate in the world.
The average price for a single-family home in the second quarter of 2025 was USD $3.25 million (AUD $4.9 million). But that’s merely an entry point, buying a smaller home in one of the town’s less desirable neighbourhoods.
What does USD $43 million (AUD $66 million) buy in Greenwich?
Last autumn’s most expensive listing offered a 1,068-square-metre waterfront home with eight bedrooms and 11 bathrooms, plus “Gatsby-like lawns”, a gym, games room, party room, wine cellar, fruit orchard, pool and spa. The front and side porches have heated floors.
Prefer something more traditional and secluded? For USD $33 million (AUD $50 million), buyers could close on an 11,760-square-metre Georgian manor on 3.2 hectares, featuring eight fireplaces, an elevator, and a dumbwaiter.
The first floor features a three-storey cascading chandelier. For bibliophiles, there’s a two-storey mahogany library. If bocce is more your pace, a similar USD $25 million compound on 7.5 hectares, built for a liquor magnate in 2009, may appeal. Fourteen bathrooms should suffice.
The Greenwich market is strong, but not without challenges.
“The big problem is that there’s no inventory,” said Evangela Brock, an agent with Douglas Elliman. “It’s extremely low at all price points.”
In November, just 15 properties under USD $1 million (AUD $1.52 million) were listed without contracts, compared with 23 above USD $10 million (AUD $15.2 million). Of those, six had contracts pending. Greenwich has more than 17,000 single-family homes.
Kanebridge Quarterly toured two mid-priced houses in Greenwich. “You don’t lose money in Greenwich real estate,” said Beth MacGillivray, a realtor with the Higgins Group. “This is the hot spot.”
MacGillivray opened the door to a 733.9-square-metre Georgian colonial in the Sherwood Farms Association development her family built in 2005. The house was expected to sell for about USD $5 million (AUD $7,743,535).
The six-bedroom, four-level house is move-in ready, with staged furniture showing its potential and many of the amenities that buyers in this range expect.
Visitors enter through a two-storey foyer with a marble floor. A circular staircase leads to an airy living room with double-height ceilings.
There’s a main bedroom with his-and-hers bathrooms, a cherry-panelled library with cigar-smoke venting, five fireplaces, and a state-of-the-art kitchen with a breakfast nook by Greenwich-based designer Christopher Peacock.
Most rooms have huge walk-in wardrobes. Even the laundry room has granite countertops. Custom millwork, cabinetry and fixtures are evident throughout.
The drawbacks? A smaller yard and no pool. Still, refugees from the city would marvel at the abundant interior space.
Not far away, an entirely different house was on the market for USD $2.66 million.
The imposing 696.7-square-metre, nine-bedroom, seven-bath Georgian/Federal home on Shady Lane in the Glenville neighbourhood was built in 1900. Its good bones and inherent grandeur were apparent, as was a clear need for updating.
“It’s a good project for someone,” said realtor Kaori Higgins. “It needs the right buyer, someone who is looking to return it to its stately original condition.”
Given the hot market, some buyers may be tempted to tear it down and build anew.
But the house is filled with charming period details, including hand-built stone fireplaces, reading nooks, pocket doors, leaded windows and beautiful original millwork.
The second floor offers a vast veranda with views of Long Island Sound and a built-in swimming pool.
The drawbacks? Bathrooms that were awkwardly redesigned in the 1970s, unsightly flooring on the upper levels, and crumbling exterior elements.
Higgins noted that a nearby sister property, fully renovated, sold for USD $11 million (AUD $17 million). Any buyer of Shady Lane’s faded elegance would need both imagination and deep pockets.
For contrast, Kanebridge Quarterly left Greenwich for nearby Fairfield’s upscale Greenfield Hill neighbourhood to visit Lion’s Gate, a 595 square metre Tudor Revival home built as a modest dwelling in the 1920s but extensively expanded and remodelled in 2000.
With three acres of land, a guest cottage, an artist’s studio and a pool house, the asking price is USD $3.3 million (AUD $5 million). Like the Sherwood home, Lion’s Gate is flawlessly move-in ready, with designer touches throughout.
The entire second floor was added during the renovation and features parquet flooring, a massive main suite, arched doorways and 2.74-metre ceilings.
Many rooms include walk-in wardrobes, extensive carved millwork and built-ins. The wood-panelled library (on the site of the former stable) is warm and inviting.
The expansive kitchen includes a window seat with a hand-painted ceiling, a wine cooler and a butler’s pantry.
Realtor Lorelei Atwood said Fairfield faces the same inventory shortage as Greenwich.
“Demand is growing as more New York-based executives are being told they have to report to the office,” she said. “Fairfield has always been a commuter town.”
Why is this home USD $3.3 million (AUD $5 million), and the Sherwood property around USD $5 million (AUD $7,743,535)?
Location. Greenfield Hill is lovely, but Greenwich real estate occupies a rarefied class of its own.
Note: Thanks to realtor Sherri Steeneck for chaperoning.
This story appeared in the Autumn issue of Kanebridge Quarterly, which you can buy here.
Rugged coastal drives and fireside drams define a slow, indulgent journey through Scotland’s far north.
A haven for hedge-fund titans and Hollywood grandees, Greenwich is one of the world’s most expensive residential enclaves, where eye-watering prices meet unapologetic grandeur.
The actress, who felt a ‘spiritual calling’ to the Harrison, N.Y., property, is asking $4.99 million for the home.
3 min
Two years ago, fed up with the long drive to the Hamptons, the actress and daytime talk-show host Drew Barrymore started looking for a weekend home in Westchester County.
When she saw a circa-1700s mansion for sale, Barrymore said, she felt a karmic connection to the Harrison, N.Y., property.
“I walked in, and I was, like, ‘I know my family’s been here. I know that I have to work on this house. I know that I’m supposed to be doing this,’” said Barrymore, 51 years old, who lives primarily in Manhattan with her two daughters. “It was like a strange, spiritual calling.”
It turned out she actually did have a connection to the area: Her great-aunt, the late actress Ethel Barrymore, had a home in nearby Mamaroneck, where an enclave known as Barrymore Lane is widely believed to be named for the family.
Barrymore bought the roughly 12-acre estate for $4.4 million, according to property records. She did an extensive renovation; she has a deep interest in interior design and has considered pursuing it professionally. “Between Pinterest, thrifting and a can of paint, there’s nothing you can’t do,” Barrymore said with a laugh.
But roughly two years later, the actress is listing the property for $4.99 million. The renovation took longer than expected, she said, and the family’s lives have changed in the interim.
The estate includes a roughly 5,600-square-foot, five-bedroom main house, a pool and a poolhouse with an additional bedroom, according to Kori Sassower of Compass.
Barrymore said she previously owned a home in Sagaponack, N.Y., but the distance from the city and the weekend traffic to the Hamptons became untenable as her children’s schedules filled up with social and sporting activities.
Harrison, by contrast, offered accessibility and charm. The property, located roughly an hour from Manhattan, is a short drive from picturesque Rye and Bronxville, while nearby Bedford has drawn celebrities. The median sales price for a home in Harrison is around $1.1 million, according to Redfin.
The property’s expansive acreage gave Barrymore a sense of being close to nature. “It’s really like being in your own personal park,” she said. “There are tons of deer. There are pheasants, there are ducks, there are rabbits.”
When she purchased the home, Barrymore said, she thought it would need only a cosmetic renovation. Instead, it turned into a “complete internal gut,” with much of the plumbing, heating and air conditioning replaced, she said.
Barrymore also revamped the ground floor to open up the kitchen, which felt dark and boxed in. “It took a year of engineering to figure out how to accomplish it,” she said.
Barrymore declined to comment on the exact costs of the renovation, but compared herself to actress Shelley Long’s character in the 1986 film “The Money Pit.”
Some of the rooms have maximalist patterned wallpaper, elaborate art walls and heavy, old-fashioned draperies. Others are minimalist. “Every little corner gets scrutinised for what it could be,” she said. “If I see a closet, it’s probably not a closet, it’s going to become some secret hideout for my kid, or I’m going to take the door off and turn it into a sculptural piece.”
In the home’s living room, Barrymore said she cycled through multiple paint colours, including pink and green.
“I painted it all green because I was dying for greenery. And then the summer came, and I was, like, ‘Oh, God, everything is green!’”
She spent time at the property even while it was under construction. When they didn’t have a kitchen, the family cooked dinner on a grill outside and drank boxed water, she said.
When workers were redoing the pipes, Barrymore couldn’t shower. “I lived in the house in the most primitive of scenarios,” she said. “It’s some of my favourite times and memories.”
When Barrymore celebrated her birthday at the property in February, she and two friends decided to grill for old time’s sake, even though the kitchen was fully functional.
“There we were in zero-degree weather with parkas, hoodies, gloves and face masks. But we were, like, ‘We gotta do it. It’s the tradition.”
Barrymore, who grew up in Los Angeles, stars in films like “Never Been Kissed,” “Riding in Cars With Boys” and “Charlie’s Angels.” Her eponymous daytime talk show launched in September 2020.
Sassower is listing the property with her colleague Brian K. Lewis in New York City.
