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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A student-run real estate investment fund is proving that hands-on experience can deliver real results. Managing $12 million in equity, the undergraduate team recently achieved a 65% gross return on its first property sale, highlighting the growing role of experiential learning in preparing the next generation of real estate professionals.
5 min
On a recent summer Sunday afternoon, Brooks Hiller was hunkered over his laptop at his apartment in Chicago, dialing in to hour three of a marathon series of conference calls on real-estate deals.
The 21-year-old isn’t a professional, and he doesn’t make a dime from this work. He is a rising senior at Indiana University’s Kelley School of Business, where he leads a team of 20 undergraduates who manage about $12 million in equity.
Those students operate their own real-estate investment business, called Sample Gates Management, named for the Gothic-style limestone arches that are the gateway to the Bloomington campus.
Unlike the many student investment clubs that deploy university money or rely on donations, the Indiana group raises funds from third parties and invests in properties across the country, such as apartment developments and industrial parks.
As a high schooler, Hiller was so enamored with the program—by most accounts, the undergraduate-run real-estate investment group that manages the most capital—that he chose to attend Indiana with hopes of being a part of it.
“Students get the experience, the school gets a better education for their students, and the investors are making their money back and get to be a part of the program again,” Hiller said. “I really wanted to be part of that.”
The group’s success is emblematic of changes transforming both higher education and the real-estate industry.
An industry that once revolved around information shared at private clubs or events has become a highly digitized landscape. It’s now flooded with standardized public-market data, so much so that undergraduates can readily peer inside and participate on nearly equal footing.
Meanwhile, colleges in recent decades have championed what is called “experiential learning,” encouraging students to do the hands-on work that will teach them the practical job skills they can’t learn in traditional classroom settings. Plus, dozens of universities now offer real-estate degrees, minors or concentrations for undergraduates.
“At its core, this program wouldn’t have existed 30 years ago,” said Harvard University real-estate professor Avis Devine.
This summer, Sample Gates Management sold its first investment, an industrial warehouse development in Indianapolis. In about 16 months, the fund earned a 65% gross profit on that property.
“That’s a really fantastic return in this environment,” one that would be “good for sort of any professional firm, not just students,” said Tim Morris, a member of the board responsible for approving the students’ investments, who is a founder and co-managing partner of the real-estate firm Proprium Capital Partners.
That property was an “easy yes” investment, Tom Peck, the students’ faculty adviser, recalled. It would diversify the group’s investment portfolio, and a reliable tenant was committed to leasing the building once it was finished, Peck said.
Most of the fund remains tied up in investments, making it difficult to gauge exactly how well it is performing overall.
A decade ago, there were only a few student-managed real-estate funds in the country. Today, there are at least 18, and two more are set to launch this school year, according to Mariya Letdin, a real-estate professor at Florida State University who has researched student-managed investment funds and advises one herself.
And yet, although a program like Sample Gates is an attractive resume line that provides unique experience among undergraduates, it isn’t necessarily a launching pad to help students secure jobs. Because of Wall Street’s summer-internship pipelines and early recruiting timelines, many of the 20 seniors in the group have already secured full-time jobs at global giants before they even touch Sample Gates funds.
In fact, the students’ professional experience—some of them participate in internships all three summers of college—is often a boon for Sample Gates. Students’ stints at institutional shops have left them with a “networking mindset” that “snowballs very quickly into a really, really good Rolodex,” Morris said.
At the Kelley School, where currently 278 students are majoring in real estate, faculty picked only 20 to manage the private-equity fund. The rising seniors were selected from Kelley’s already competitive roughly 60-student commercial real-estate workshop, in which students analyze deals and pitch them to mock committees.
In 2022, for the group’s first round of fundraising, Sample Gates raised $4.2 million from 46 investors, 40% more than their goal of $3 million. Last year’s cohort raised $7.8 million from 74 investors in the second round of fundraising, with one investor forking over $700,000. Some investors put money into both funds.
Many of the investors are Indiana alumni now working in the real-estate industry themselves. They expect the students to return a profit, but they are also enthusiastic about fostering the young program and meeting standout students.
The student managers screen between three and eight deals each week, which could mean they evaluate up to 400 potential investments a year. However, between 2023 and 2025, they selected only 12 investments, ranging in location from Indiana to Arizona.
Once a potential investment passes an initial screening, a team builds financial models and meets with prospective partners to pressure-test the viability of a deal.
For students to move forward with an investment, they must present it to their investment committee, a board of 10 seasoned real-estate executives. The committee has to sign off on all deals, and they reject roughly a third of the ones the undergraduates bring to the table.
And if the students think they can pitch an investment without getting their eyes on the physical property—regardless of where it is located— they would best think again.
Some observers predict that students might be disappointed when they start their full-time jobs because of the shift from doing the highest-level work of managing a fund to being a lowly analyst at a large firm.
“To have all of these skill sets in a short period of time and then to go be an associate for Blackstone would be mentally defeating,” said Rhett Trees, an investor in Sample Gates and Indiana alum who is the chief executive of a Denver-based real-estate private-equity firm.
