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.
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Kit Braden, an executive at French beauty empire L’Occitane, has spent every winter for the past 13 years at the stone vacation home.
2 min
A historic Barbados estate with a 300-year-old villa and 11 acres overlooking the Caribbean Sea is now for sale with a guide price of $22.5 million.
The seller is Kit Braden, chairman of the U.K. branch of French beauty empire L’Occitane Group, whose family has spent every winter for the last 13 years at the island property, known as Fustic Estate.
“It’s very much a family house,” Braden said. “We love having a lot of people there. It’s a collection point to keep everyone together.”
The main villa dates to 1712, though it’s been reimagined and expanded substantially over the years.
It spans 13,000 square feet and features seven en suite bedrooms across three wings, as well as expansive verandas, stone courtyards and rows of louvered doors in gay Caribbean pastels.
In the 1970s, when the home was owned by Charles Graves—brother of British poet Robert Graves—it was reimagined by stage designer Oliver Messel, one of the foremost theater designers of the last century. Messel expanded the home, added a lagoon pool with a natural waterfall and other theatrical features, according to Braden.
“The whole place is a little bit magical,” he said.
The home sits about 350 feet above the water, and surrounded by lush gardens that slope towards the water.
“We look down through our garden—which is about 12 acres of tropical gardens and palm trees and wonderful old mahogany trees—onto the Caribbean,” Braden said.
He and his wife first saw the property on New Year’s Eve 2013, during a quick trip from where they were staying in Grenada.
The couple spent an hour walking the perimeter, some of it still untouched jungle, in the pouring rain.
“By the time we got back, I had fallen in love with it,” Braden said.
His wife, however, wasn’t so sure. But in Braden’s telling, a second visit in sunnier weather with two of their children brought her around.
“She had to be talked into that it was a jolly good idea; now she absolutely loves it,” he said.
When they bought the property, the edge that runs along the waterfront was a jungle, so they cleared the ridge and transformed it into gardens.
They also bought an additional sea-level parcel with two beach cottages, giving the property direct access to the water and the town below via a five-minute walk.
The property also has a 15-person staff, a reflecting pond, an outdoor pavilion suitable for yoga and a commercial grade kitchen that can serve more than 100 guests, according to a brochure from Knight Frank, which posted the listing in March. They did not provide further comment.
For Braden, the property is special because of its natural beauty, its proximity to the town of Saint Lucy and its history—which dates way way back to when the island of Barbados was first formed via tectonic activity.
“It was basically tectonic plates that collided about a million years ago so the seabed is the top of the hill,” Braden said. “We’re on coral rock.”
As a result, Fustic Estate includes an extensive network of caves that were likely used by the Arawaks, a Venezuelan fishing tribe that followed the fish to these islands about a thousand years ago.
“If the fish were good they’d camp here,” Braden said. “There’s evidence that they stayed there in those caves, they lived there in good winters.”
Now it’s someone else’s turn to live on the land shared by Arawaks, the plantation owners of 1712, Charles Graves and the Braden brood.
