Selling Multimillion-Dollar Homes On A Smartphone

Q. What is it like to do a remote transaction with a client on a multimillion-dollar property?

Ryan Flair

Partner, ranch broker at Hall & Hall in Bozeman, Mont.

I had been working with this client for close to 18 months, so I had a general sense of what he was looking for. Then Covid kind of creeps up and puts us in a situation. We were all in lockdown and couldn’t do much. No one was flying commercially, you had to quarantine for 14 days if you came in from outside the state. My client wasn’t inclined to travel.

One of my partners had a client with a really beautiful property that hadn’t been on the market in a long time—a 20,000-plus-acre ranch. He let us know it was going to come on the market.

I was texting with my client and he said, “I’m very interested, let’s learn more.” We had a tour of the property—five brokers in five trucks—with the ranch manager in his truck. I’m taking photos with my smartphone, and video and panoramas and narrating them, and as soon as I get back service, I’m sending them to him. I went back a separate time and spent six hours there, going around the ranch taking videos on my phone and geo-marking them on a map so the client could see where they were.

One of the most challenging things about the property is access. I had to video myself driving—“Hey look, this road isn’t great, you need to understand you’re not going to drive a motor home on it.” He does have a motor home—one of those super high-end ones.

We put in an offer. This wasn’t a couple-million-dollar deal, it was a very large price tag. My client knew it was one of those rare ranches that don’t come along often. Once we got the ranch under contract, we hired a helicopter. I did the same thing with my iPhone—taking video and narrating from the helicopter.

The sale closed before my client saw it. There were a lot of sleepless nights for me. The first people to see it were his family members and friends—so, hey, no pressure. But he loved it. The guy ended up with a great ranch. It was one of our biggest sales that year.

Jeremy Stein

Associate broker, the Stein Team at Sotheby’s International Realty, New York City

We were approached by clients—friends more than clients—who wanted to sell this absolutely spectacular townhouse in the heart of Greenwich Village. They owned homes in different parts of the country and had thought about living a different way. Then when Covid hit, it made the decision a lot easier for them.

We put it on the market for US$28.5 million. We created a very high-end video of the property, and we did a 3-D Matterport scan, which allows you to tour every nook and cranny. We had a number of virtual showings over the summer, where agents would come and FaceTime with their client in the Hamptons or Jackson Hole or Europe or wherever. We got an offer in the mid-$20 millions. Then an agent I know called and said, “I have a client who is not in New York. They’d like me to come and take a look at it and maybe FaceTime.”

So we did a FaceTime tour. I walked them through the house, just as if they were behind me, as their broker held the phone. I pride myself on reading buyers. Some don’t want to be talked to at all, and some are like, “Show me every drawer.”

I didn’t have that ability to see how the people were reacting. I did see her face to say hello, and from time to time the camera may have gotten turned so we were looking at each other.

These buyers wanted to know about the air conditioning. Maybe a few times they wanted to see what the view was like. If we went to the window, she was, “Oh, can you tilt up? What does the sky look like?” To this day, I don’t know who they are.

Soon after, I got a call from their agent, who said they’d like to make an offer: $27 million. She said, “But we want you to not show the house and not to entertain new offers, we really want exclusivity.”

My clients said, “We’ll do that, but it’s going to cost $1 million.” So we said $28 million. They accepted and we went to the contract stage. It closed last year in November. A few months after the closing they still hadn’t seen it.

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.

Selling Multimillion-Dollar Homes On A Smartphone

These agents explain what it’s like to close high-end deals virtually.

Q. What is it like to do a remote transaction with a client on a multimillion-dollar property?

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.