The Wild, Wonderful World of Estate Sales

An estate sale is only a true estate sale if the homeowner is dead. If the owner is living, then it’s a tag sale, though many people use the terms interchangeably. When I went to one of my first “estate sales,” in Hewlett Harbor, Long Island, roughly two years ago, just before the pandemic temporarily forced much of the industry online, I was surprised to discover that the owner was not only alive but there, in her soon-to-be-former house. A recent widow, she wandered through the rooms, dazed, dressed in a fringed denim vest.

The house was a beige Colonial-style four-bedroom with prim hedges and a small, sloping lawn. I arrived thirty minutes early, but a long line had already formed outside; people were peering into the windows, hands cupping their eyes. When I introduced myself to one of the elderly women up front and admitted to her that I was a newbie, she promptly pulled me into a hug. “You’ll find that this is a culture,” she said. “It’s like an addiction!”

At 10 A.M., a slim, brunette woman wearing a long-sleeved shirt that read “Full of Surprizes Estate & Tag Sales” emerged from the house and walked onto the lawn. The regulars recognized her—she was Madeline Winn, the owner of the company that was hosting the sale. The group surged toward her like an audience at a concert as she removed a sheet of paper from a plastic shopping bag and cleared her throat. “Ricardo M.?” she asked, reading off the sheet. “Allen C.?”

The sheet, I later learned, was “the list”—one of the many aspects of estate-sale culture that is at once quaint and slightly murderous. Hours before a sale begins, an estate- or tag-sale company will put out a sign-in sheet that determines the order in which people will be allowed into the home. The first few names on the list are always “pickers”—estate-sale obsessives, usually low-level furniture, silver, or jewelry dealers—who wait outside the sales for most of the night in their cars, sometimes in teams, with each person taking a shift. Next are the fervent hobbyists—one of Winn’s regulars, for example, is a man who really enjoys carving things out of oak, “so he’ll buy anything oak”—and the decorators on repeat pilgrimages for a client, such as an interior designer I met, who was working for a woman who “loves everything parrots.” There are also the higher-level dealers with brick-and-mortar stores (or storage units), who show up in vans and take four or five of the most expensive furniture pieces first thing in the morning. They resell the pieces at secondhand boutiques in Williamsburg and Chelsea or on eBay, charging at least thirty-five per cent of the original price.

As Winn called out names from the list, the buyers lunged inside, hands grasping, necks swivelling. It was as if each person in the line had discovered, in the night, that they had contracted a unique disease that could only be cured by obtaining a Lucite napkin ring or an official Barbra Streisand memorabilia plate. Prices ranged dramatically—a nice umbrella was twenty bucks; a hand-carved clock was just over a thousand dollars. The buyers ran through the house possessed. “Where are the posters?” someone screamed, kneeling in front of a stack of frames. Nearby, a clothes hanger, recently rid of its contents, swayed. One man clutched five belts. Another had a shower caddy looped around his finger.

By 12:30 P.M., everyone on the list had made their choices. The early-bird buyers looked rumpled, like travellers moving through baggage claim. Winn began to slash prices—a chandelier went from twelve hundred dollars to seven hundred and fifty. Around her, people grew contemplative. “My father loved animals,” one woman said, staring at a framed needlepoint screen, which featured a dog and cost four hundred and ninety-five dollars.

At that point, new customers started trickling in—women wearing leggings and couples looking fresh-faced, people who had stumbled upon the sale during a jog or a family outing. They marvelled at the offerings, usually with no intention to buy. “Beautiful. A steal!” a well-dressed man said. “Look at these old ’45s!” There were also people who had come to buy the basics: food, sheets, napkins. Winn, whose job is to get the best price for the homeowner, haggled over everything. When a woman and her daughter wanted to buy an old lunchbox, Winn drove a hard bargain, using the same line that she’d used earlier when negotiating the price of a twelve-hundred-dollar beaded chair: “It’s gorgeous. I can’t part with it for less.”

Now, too, came the streams of the very elderly, who, you couldn’t help but think, didn’t look too far from holding estate sales of their own. “Someone once tried to buy my dishes for eight thousand dollars,” one woman told me. “And I wouldn’t sell. Do you know why? My grandmother’s hands were on those.” She raised her own hands and shrugged. “My kids couldn’t care less.”

Estate- and tag-sale companies mainly deal with two generations: homeowners born during the Great Depression, who have either died or are moving into assisted living (in the United States, one of the bigger organizers of estate sales is a downsizing franchise called “Caring Transitions”), and boomers looking to pare down. The groups have different reputations in the business. Depression-era homeowners are known for their pack-rat behavior, and the boomers are known for just having a lot of really nice stuff—the result of having lived through the perfect time in history to consume amply in early adulthood. On the horizon lie the millennials, a fuzzy, aimless group often characterized as having little reverence for antiques and collectibles, and having no money to buy such things even if they want to. “It’s a cliché, but I really do think millennials like experiences most,” Lark E. Mason, Jr., a longtime appraiser and expert with Sotheby’s who often appears on the PBS television program “Antiques Roadshow,” told me.

As a millennial, I thought that sounded right. My friends and I grew up on a profusion of cheap goods from Target and entered our first apartments lugging crackable, plastic under-bed drawers from Marshalls and Amazon. We also grew up on a steady diet of home-improvement reality TV, where much of the fun of living anywhere seemed to lie chiefly in remodelling your place to look like everyone else’s. But, I thought, I would never be able to afford to buy my own home anyway. The one “antique” dresser that I ever bought myself was off of Craigslist, in Boston; I left it two apartments later in Rhode Island. Why keep lugging such a heavy armoire from rental property to rental property?

Unlike the auction world, the estate-sale world is unregulated—there are no official rules for how much companies can charge for their services.

I started going to estate sales for the deals, but I rarely bought anything. (Estate-sale prices are lower than prices at New York’s curated secondhand shops, on average, but they aren’t yard-sale prices; a two-hundred-and-fifty-dollar sweater, with its original tags, might go for forty or fifty bucks at an estate sale.) Usually, I just watched—the people, but also the homes. It was like trick-or-treating or spying, but with the rubbernecking undisguised. Part of the fun was being able to do some light detective work about the owner. You could often tell, based on their book collection, if they had split with a spouse or made a career change. The physical placement of the objects themselves also yielded certain clues: in some houses, only the lower shelves, at the height accessible by wheelchair, were filled. But the most interesting people to speculate about were the ones whose possessions seemed to contradict each other—one house I visited had both a prominently featured memoir of Laura Bush and, in another room, a commemorative Soviet Union hat. At each sale, my eyes would trace the piles slowly: all the Christmas decorations, a dusty juicer sitting like a cat in the sun. The houses tended to be nice, but not so nice that I wished I lived there. An estate sale brings out the facts of living that are true for people of any income bracket: paper plates and tennis shoes multiply like rabbits. White furniture always grows brownish over time.

High-end estate sales, such as when Christie’s auctions off a Rockefeller collection, are different. The items are highly curated, and they are not sold within the actual home; auction houses display them in immersive, museum-quality exhibitions, which reel in collectors from all over the world. These events are also relatively infrequent. (In 2021, between July and September, there were just twenty New York auctions at Christie’s; in the second week of July, within thirty miles of my Zip Code, there were a hundred and sixteen estate sales.) The vast majority of New York’s in-person estate and tag sales take place in the outer boroughs or Long Island, at normal-seeming houses that are abnormally full of resellable objects: nearly new recliners, Barbie dolls in their original packaging, blenders in tip-top shape. It was a fun paradox to behold. Each sale was also a vocabulary lesson. “See this?” Winn asked me, holding up a fringed blanket draped over the edge of an H. W. Perlman antique piano. “This is called a piano shawl.” There were so many vestigial words—“wall pockets,” Hummels, Lladró—the last, referring to a Spanish figurine company, used as a shorthand for both finery (“Well, it’s not a Lladró piece”) and kitsch (“I didn’t come all the way here for Lladró”).

At the estate sale in Hewlett Harbor, the elderly woman who had refused to sell her dishes was searching for statuettes to display. For less than fifty dollars, she’d bought a Lladró, which she considered a prize. Winn handed it to her wrapped in newspaper, saying, “Hold it like a baby.”

Antiquing is a relatively recent invention. It came into being after the First World War—a by-product of the consumer culture of the nineteen-twenties, enabled by the invention of the automobile and the emergence of the concept of the hobby. Since its inception, the market has relied on the ability of one party to exploit privileged market information over the other. This is what allows resellers to rip off buyers in gentrified Brooklyn, but it’s also what drives the flow of valuable secondhand goods from private homes into the antiques market to begin with. In her book “Out of the Attic: Inventing Antiques in Twentieth-Century New England,” the social historian Briann Greenfield describes how, at the beginning of the twentieth century, when the value of antiques began to rise, a middle-class cadre of enterprising “junk snuppers” began departing in cars from urban centers to the countryside, where they knocked on farmhouse doors and kindly offered to relieve inhabitants of any mint-condition Americana. She cites a 1907 antiquing guide called “The Quest of the Colonial,” which advises junk snuppers to identify possible marks by looking for “the sight of chairs on a porch.”

In the nineteen-fifties, an explosion of advice manuals positioned estate sales as a knowledge trade—a way for middle-class housewives to score quality goods that might elevate their family’s social standing. The contemporary styles of that era, in turn, have played a major role since: “mid century” has been one of the most searched-for terms on, the industry’s premier site for estate-sale listings, for at least a decade. Being less than a hundred years old, of course, mid-century furniture won’t be strictly antique until around 2050, but as the concept of antiques gets older, and as new terms begin to emerge (upcycled, repurposed, salvage, vintage), the definition of “antique” has slackened. “In an effort to salvage waning interest among younger buyers,” Maxine Carter-Lome, the publisher of the Journal of Antiques and Collectibles, recently wrote, “the word has been appropriated to include an eclectic mix of generally old things.”

The average antique collector’s connection to history has also shifted over time. The market for early American antiques, perhaps the first and most popular antique genre, waned significantly toward the end of the twentieth century. Greenfield said she doubted that the market would ever recover; fewer would-be collectors have knee-jerk positive associations with the material history of the early United States. “I think recognizing that the past is much more complicated has undermined that movement,” Greenfield said.

The market for collectibles and memorabilia related to the Black American diaspora, on the other hand, is rapidly growing. The Asian art market has also been roaring for decades, especially as more and more affluent Chinese buyers compete with Americans in online auctions for Chinese art and artifacts. Gail Deculus-Johnson, a collector of Black Americana, and the president and co-founder of the African-American Memorabilia Museum and Cultural Arts Center, first started collecting in the nineteen-eighties. At the time, many sellers didn’t consider representations of Black Americans to be particularly valuable, unless they knew that they were selling to someone “looking for Black stuff,” she said—in which case they’d quickly jack up the price. Deculus-Johnson’s collection includes documents and objects related to slavery, such as shackles and civil-rights memorabilia. “Now,” she said, “our Black population is really seeking these items.” Both Oprah and Whoopi Goldberg are known to have had Black Americana collections.

In January of 2020, I drove through the streets of Brooklyn with Paul Dunn, the owner of Lucky Rabbit Estate Sales, to visit two potential clients. At a stoplight, he flicked through thumbnails of photos of a client’s possessions on his phone: a grandfather clock, an entryway bench. Distinctive pickers acquire nicknames once they’ve been on the scene for long enough—Radio Rob, Tom Chicken Broccoli, Lexus Mike, Victor No Shoes—and before he opened his own company, Dunn was known as Alcohol Paul. When he got into estate sales, after the 2008 financial crisis, he developed a specialty in reselling vintage alcohol. “I could buy a bottle of Cuban Bacardi for five bucks and sell it for five hundred,” he said, “depending on the label.”

The first place we saw that day was an apartment above a pharmacy, in Bensonhurst, where two adult daughters pointed out the primo items: their late mother’s adjustable Craftmatic bed (“She didn’t die in it!”) and a set of prim undergarments that had been hand-sewn for her wedding in 1958.

Dunn didn’t think that they had enough for a sale. As we left, he told me, “I didn’t want to tell them, ‘Sorry for your loss.’ They actually seemed kind of jovial.”

The next house was in Crown Heights. The woman who answered the door had honeyed hair, a cherry-red manicure, and an Apple Watch. She’d just flown in from California. “There’s no light switches in here,” she warned us. Inside the house was mustard wall-to-wall carpeting and a gigantic Maitland-Smith desk with an ink blotter. Across the room was a phonograph. A set of built-in shelves had been covered hastily with cardboard. “We didn’t want the nephews taking what doesn’t belong to them,” she explained, tearing at the tape with her red fingernails.

“My father-in-law was the nephew of Chajim Bloch,” she continued. “He was the author of ‘The Golem.’ He was captured by the Nazis and immigrated to New York in 1939. That’s his library.” She pointed to where the bookshelves extended into the next room.

“We have some experience with stuff like this,” Dunn said. “The Jewish art does very well.” He rapped on the Maitland-Smith desk. “Nice desk.” He flipped over the edge of a rug to look at its underside, running his fingers along the stitching.

“Is there a lot in the basement?” he asked, hopeful.

Everyone who loves estate sales has the same dream tucked inside them somewhere, like a name written inside a T-shirt collar. It’s the dream of the special find—the dusty baseball card of great value that just sort of calls to us, the weird sculpture that turns out to be a priceless masterpiece. It sounds like fantasy, but the stories appraisers tell about real finds almost always begin at an estate sale or low-end auction house. People uneducated in antiques often share the same misguided ideas about how much old things are worth. “Everyone thinks old shaving mugs are worth something,” one art appraiser told me. Most are worth less than a hundred dollars, “unless they have a transportation or occupation theme,” she said. Meanwhile, few people assume that old artworks are necessarily worth money. In 2016, a low-level reseller bought a pen-and-black-ink drawing for thirty dollars at an estate sale in Concord, Massachusetts. Recently, it was revealed to be an Albrecht Dürer that is estimated to be worth many millions. In the South, unsigned animal figures by the sculptor William Edmondson—the first Black artist to have a solo exhibit at the Museum of Modern Art, in 1937—which are worth hundreds of thousands of dollars, can be found in the back yards of people who bought them as lawn ornaments.

In one of the most popular clips of Lark E. Mason, Jr., the Sotheby’s appraiser, on “Antiques Roadshow,” he is brought to tears by a Tang Dynasty statue. “It’s fantastic,” he tells the statue’s owner, who looks bemused—her grandparents had bought it on a trip. “And where have you had this since then?” Mason, Jr., asks her, pained. “My mother had it in her house and I inherited it,” she says, adding that someone once told the family it was from the Ming Dynasty. Mason, Jr., informs her that it’s older than that. “This . . .” he said, his voice breaking. It’s a fascinating display—years of education culminating not just in knowledge but in the ability to be suddenly felled by recognition.

Many of the objects Mason, Jr., deals in no longer have much mystery: they possess chains of ownership and pedigree, and a lack of flaws that makes them the perfect vehicle to embalm a particular historical period. They are, in the parlance of appraisers, “collectible” art—something fine enough to matter to a rich person, or to an institution, and that will “tell the story of society, of life,” he said, “for all of us.” The kinds of meaning objects acquire at estate sales—the mysterious sentimentality surrounding an object that has been disgorged from an unknown person’s life, and the idea that it could improve your residence, or your day—don’t exist in the world of collectibles. When I asked about estate sales, Mason, Jr., spoke about them as if trying to find a way to compliment pocket lint. “I think that they are very interesting,” he said carefully. “I think that there are many opportunities for people who are interested in making discoveries.” He paused. “Going to those on a regular basis is, um, not something that I would want to spend my time doing.”

And yet. How did he get into antiques? “My uncle had a wonderful kind of estate-sale type of business in Tallahassee,” he said. “I remember as a child going in, and he’d have rooms of books. One year, he bought a circus. Who buys a circus?” He laughed. “It had the funny mirrors and that game where you have the big mallet that hits the big thing that shoots up?” Mason, Jr., searched, but he couldn’t find the word for it.

Unlike the auction world, the estate-sale world is unregulated—states have different rules about whether estate- and tag-sale companies must possess business licenses or collect tax, and there are no official rules for how much companies can charge for their services. There is also nothing stopping companies from charging certain customers more or less. “I got into this many years ago because I saw the elderly being taken advantage of, especially those with dementia,” Julie Hall, the director of the American Society of Estate Liquidators and a thirty-year veteran of the estate-sale business, told me. In one of her numerous books, which include “Inheriting Clutter: How to Calm the Chaos Your Parents Leave Behind” and “What Am I Going to Do with All My STUFF?,” she describes a woman with Alzheimer’s whose friends and neighbors, hearing that she was going to be institutionalized, showed up at her house and began looting the place. “What I witnessed,” Hall wrote, “was like watching a vulture strip a bone.”

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