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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The US housing market remains under pressure as high mortgage rates continue to weigh on affordability and demand. Industry leaders say 2026 has been one of the toughest years for home sales, with slower price growth, weaker mortgage activity, and fewer buyers entering the market. However, experts say reduced competition and more price cuts could create opportunities for well-prepared buyers.
2 min
The typically busy spring season for the housing market was a dud, and the summer isn’t looking much brighter.
Housing services companies like Zillow Group and Rocket RKT +3.78% were loud and clear last week on earnings calls: Rocket CEO Varun Krishna called the quarter through June “one of the toughest spring housing markets in years.”
Jeremy Hofmann, Zillow’s chief financial officer, said on a conference call that the company predicted earlier this year that the market for mortgages would be flat. “We actually now think it’s going to be down low-to-mid-single digits,” he said.
The rest of 2026 will remain challenging for mortgage origination volume, says KBW analyst Bose George. The question now is what happens in 2027. “If mortgage rates remain [around] 6.75%, I think that’s going to be challenging even for next year,” he says.
But what’s bad news for mortgage companies could be a positive for bargain hunters. Buyers can expect prices to grow more slowly—or mildly decline—with less competition as long as mortgage rates remain unpredictable.
Mortgage rates at the beginning of the year were solidly below year-ago levels, notes Zillow senior economist Kara Ng. But they surpassed last year’s levels recently, she adds, referencing Freddie Mac’s weekly survey of 30-year fixed mortgage rates. Last week’s reading, at 6.69%, was higher than year-ago levels for the first time in 2026.
“From the affordability point of view, it’s going to get more challenging in the second half of the year,” she says. “And when affordability gets more challenging, that impacts sales and home price appreciation.”
Mortgage application data tracked by the Mortgage Bankers Association has cooled since the beginning of the year. The trade group expects that the number of mortgage originations in the remaining two quarters will lag behind last year’s levels, after exceeding 2025 levels in the first half.
Rocket’s early-stage data—which the company told Barron’s it derives from its brokerage Redfin, demand for its mortgage products, and signs in its servicing portfolio that a homeowner is preparing to refinance or move—“leads us to expect the third quarter mortgage market to be smaller than the second,” Chief Financial Officer Brian Brown, said on the company’s call. He added that such an occurrence is “something the industry has not seen since 2022.”
Prices will be about flat nationally, Ng says. Zillow’s most recent forecast, which shows how values are expected to change in the year ending June 2027, show them dropping in roughly half of the 100 largest U.S. metros for which data is available.
Buyers aren’t rushing in at a time when mortgage costs are rising and unpredictable. But those with the right combination of patience and cash could stand to benefit. “If you are financially qualified to buy a starter home, you are facing less competition and you’re more likely to get a price cut,” Ng says.
