The aptly named Nearwater Lane, in the Connecticut shoreline suburb of Darien, is the sole route home for those Wall Street titans, corporate executives, and heirs to privilege who inhabit a peninsula known as Noroton Neck. Breaking away from the commercial congestion of the Boston Post Road, Nearwater makes a beeline through the verdant cape, passing beneath old-growth shade trees and along deep front lawns, past the closely clustered homes of a private beach community, past the entrance to the town beach, and finally halting at the waterfront estates that claim the peninsula’s furthest tip on Long Island Sound. The lane is the only access way onto the Neck, whose curved appendages protect enough coves and inlets to make the area a haven for sailing enthusiasts. Developers spotted its potential as early as the 1920s, when Thomas Crimmins, the son of prosperous Irish immigrants, began carving a portion of the peninsula into building lots.

After dredging the harbor on the east shore to create a yacht basin, Crimmins’s company built a pier on the west shore, subdivided the land, and designated a private beach for the exclusive use of property owners. According to an easement laying out the extent of those beach rights in 1931, “bona fide” guests of the property owner were welcome but with some exceptions: beach privileges were never to be extended to “any person or persons of the Hebrew race.” For several decades thereafter, Darien would come to be known as a community almost wholly reserved for white Protestants. Sociologist and author James W. Loewen has gone so far as to label Darien a “sundown town,” the term for towns that actively kept out African Americans and other groups in the interest of remaining “all white.”

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If anti-Semitism no longer distinguishes Noroton Neck, it is still, like much of Darien, a province of privilege. And members-only socializing remains a hallmark of Darien life. The town of twenty thousand has no fewer than eight private clubs, including three country clubs and a hunt club. At the top of the social pecking order is the highly selective Wee Burn, an old-line golf club where debutantes were once feted at fancy cotillions and female club members were still fighting for full club privileges as recently as 1997. Darien has its own barriers to entry. Single-family homes sell for an average of $1.6 million. Starter homes—in the $600,000s— are generally found in densely developed Noroton Heights, which once housed the European immigrants who serviced the old estates along Darien’s coast. Prices rise precipitously the closer one gets to the coveted shore communities, which, in addition to Noroton Neck, include Long Neck Point, Contentment Island, and Tokeneke. These are aspiration addresses, locations that telegraph status. On Nearwater Lane, in 2010, a six-thousand-square-foot colonial with a three-car garage and in-ground pool on two acres fetched nearly $5 million for its then-owner, Richard C. Breeden, the former Securities and Exchange Commission chairman.

Buyers here commonly pay multiple millions for homes they fully intend to tear down and replace with something grander. They aren’t just paying for the bucolic landscape and water views— figuring heavily into their investment calculus are also privacy, security, and resale value. What they ultimately want, however, is something without a definitive price tag. As the residents of Nearwater Lane were reminded a few years back, no matter how much you shell out, it’s never enough to buy certainty.

It was Christopher and Margaret Stefanoni who upset the social order after moving to 77 Nearwater Lane in 1999. A couple of brainy Harvard grads, they came from starkly different backgrounds: he, a scrappy athlete raised by a struggling single mom in Massachusetts; she, a quiet, self-described nerd who grew up in Guatemala, where her Harvard-educated parents ran a coffee business. According to Chris, they found each other in Cambridge, grew close while working together on real estate deals, and wound up eloping. When Chris decided to put his MBA to use in a finance career, the couple decided to move closer to New York City.

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In some respects, Darien was a natural landing place. The train commute into the city was a tolerable forty-five minutes. The town’s sixteen miles of coastline appealed to Chris, an avid swimmer. The couple’s young son could attend the excellent public schools (as would his four siblings to come). And Margaret, who goes by Peggy, had strong family ties to the town; as a child, she’d often visited Darien to see her grandfather, who was chief of clinical chemotherapy at the Sloan-Kettering Cancer Center.

If Darien seemed right for the Stefanonis in theory, in practice, the Stefanonis were not at all, and nor did they aspire to be, the Darien type. Perhaps Chris harbored resentment toward the rich from a childhood spent in want. Perhaps Peggy was put off by Darien’s homogeneity compared to life in Guatemala. Whatever the reasons, the Stefanonis placed little value on fitting in. They weren’t interested in club memberships. They did not take exotic vacations or dine at fancy restaurants. And they eschewed the kind of luxuries that advertised wealth. Happy with thrift-shop finds, Chris tended toward Dickies, Peggy toward loose-fitting sweaters. Instead of Range Rovers and BMWs, they drove a well-worn minivan and a vintage Volvo. They were certainly sharp enough to know how the social climbing game was played—while at Harvard, Chris had made his way into one of the exclusive male final clubs. But they derived far more satisfaction from bucking the norms than hewing to them.

This attitude of nonconformity extended to their approach to real estate investment. While living in Massachusetts, they had practiced ferreting out undervalued properties and removing encumbrances to make them buildable, mainly in affluent areas. Chris’s rule of thumb was that the best deals are the ones no one else wants. In Darien, 77 Nearwater seemed to meet that litmus test. A dated contemporary, it was nothing special—any other buyer would have probably torn it down and built anew. The draw for the Stefanonis was the one-acre lot and its location next to a large tidewater pool known as Holly Pond. Although the property didn’t include frontage on the pond, an easement across a neighboring property to the back guaranteed access to the water. Trees blocked the view from the house, but trees weren’t permanent. The Stefanonis saw potential and snatched up the property for $800,000.

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They hadn’t been there long before they hired contractors to clear away trees and vegetation. Relations with the neighbors quickly soured, especially since the cutting strayed over property lines. The town insisted that the Stefanonis restore some of the plantings, which were within a regulated coastal zone. Tensions eased temporarily, until another point of contention arose: the Stefanonis began to zealously pursue dock rights on the pond, a privilege their neighbor believed was rightfully his. The discord worsened, and the battle over easement rights moved from their backyards into the courts.

Even as the legal battle played out, however, the Stefanonis hit upon another way of upping the value of their property. This approach didn’t demand compliance with so many expectations and regulations, and would perhaps even accomplish a public good: in compliance with Sec. 8-30g of the state laws, the Stefanonis had decided to tear down their house and replace it with an affordable-housing development.

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If the Stefanonis’ proposal made a mockery of the surrounding neighborhood’s exclusivity, under the law, it was also very viable. When the plan was announced, the neighborhood reaction was absolutely apoplectic. “People were violent,” recalls Evonne Klein, the first selectman at the time. “I had a guy put his fist in my face: ‘You haven’t done anything about this. You need to do something about it!’”

The Stefanonis’ plan called for twenty condominiums in two structures designed to resemble a manor house and barn. Six of the condos would be offered at below-market rates of $160,000 to $220,000. The project was to be strictly for seniors, and the need for such housing was undeniable. The Clock Hill condos always had a waiting list of buyers, and renters were lined up sixty deep for the rare opening at the town’s thirty-unit elderly-housing complex.

But angry Noroton Neck residents didn’t want any high-density housing on Nearwater Lane. They saw the project as not just a threat to the single-family sanctity of their own neighborhood but to the town as a whole. “We do not want to set precedence [sic] for other areas in town if this goes down so easily,” warned an e-mail circulated by opponents.

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The Stefanonis’ immediate neighbors fumed that the affordable-housing plan was a form of retaliation for their objections to the land-clearing and claim to dock rights, a charge the couple has consistently denied.

Regardless, their plan had struck a more central nerve in town, evidenced by the turnout for the planning and zoning commission’s first public hearing on the matter. Although it was a weeknight, several hundred people packed the town hall auditorium. Chris Stefanoni had alerted local media about the hearing, and their presence only added to residents’ ire. One man cursed at a television cameraman, suggesting he go cover something else. When the Stefanonis began their presentation, the crowd hissed and snickered, eventually prompting a scolding from the commission chairman.

That evening was the beginning of an extended stretch of mutual vituperations. The Stefanonis were not cowed by the rudeness and open resentment, an outpouring that would continue well beyond that evening. Far from intimidated by the town’s wealth, the Stefanonis would deflect accusations of greed hurled their way by seizing on Darien’s pervasive privilege as evidence of the need for housing diversity. Darien was too sheltered and overwhelmingly white, they crowed, pointing to the high school parents’ association’s pitch for a “slave auction” as a possible theme for that year’s post-prom party. Chris Stefanoni publicly reveled in the notion of an 8-30g housing complex nestled in among the rich and powerful. “It would be a lot easier to just build a McMansion, sell, and move to another town,” he told me at the time. “But Darien has enough McMansions. Darien needs some humility.”

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The Stefanonis were uniquely suited for this fight. They lived like paupers in a sparsely furnished house, managed to do their own legal work, and avoided debt. (The only status that has ever seemed to concern them is the athletic standing of their children.) And they were extraordinarily persistent. In short, they had staying power, so much so that the battle over 77 Nearwater dragged on for a full two years. Chris had abandoned the notion of a job on Wall Street; he focused all his attention on the housing fight. When the dust finally cleared, the condo project was off the table— but the Stefanonis were millionaires. An anonymous donor or donors had effectively bought them out. Delivered in the form of a grant from the New York Community Trust to the Darien Land Trust, the money enabled the land trust to acquire the property. The Stefanonis’ price: $4.2 million.

Chris says that he and Peggy took the deal because it beat the alternative—opponents of their proposed affordable-housing project appeared ready and willing to keep the Stefanonis’ development plan tied up in the courts for years. The price reflected the property’s new development value—and, for the anonymous donor(s) perhaps, the cost of future certainty. Today, 77 Nearwater is a lovely wildflower meadow.

Was this the Stefanonis’ plan all along? Was their 8-30g application a ruse, a high-stakes game of chicken? Many people in Darien thought so, especially after the couple began to buy up more property in town. They have since filed three more 8-30g applications, all for senior housing. Some call the Stefanonis extortionists; a local lawyer who went to Hartford to rail against the affordable-housing law before a legislative panel took it a step further and, without mentioning any names, declared that, in Darien, 8-30g had become a tool for “economic terrorism.”

Chris acknowledges that his motives for pursuing affordable housing are not pure—“I’m not altruistic.” But he doesn’t see himself as any worse than the rest of the diehard capitalists who live in town—and perhaps a little better. “I’m not like the guys on Wall Street who are gambling with other people’s money,” he says. He and Peggy simply found a niche: Darien’s long inaction on affordable housing. And if financial gain is one aim, they also firmly believe that Darien is long overdue for the economic and racial diversity such housing could bring.

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In effect, they have become Darien’s worst nightmare: canny crusaders who are persistent, vocal, and unconcerned with status. They are opportunists waving the banner of social justice, attention-getters in a town that prefers to conduct business unnoticed.

They are not what the drafters of 8-30g had in mind, and rare is the developer who could or would exist as the Stefanonis do: in a constant state of legal warfare. As Chris himself says, “You gotta be a little bit nuts to do this.” But if the Stefanonis are extreme, their unflagging presence has also forced Darien to have the necessary conversation it did not want to have. And, in this way, 8-30g has served its purpose. Darien has had to confront the reality that if the town does not plan for and generate more affordable housing on its own terms, then the Stefanonis might do it for them.

* * *

More than half a century has passed since the release of the film "Auntie Mame," in which the exuberant, free-spirited Mame, played by Rosalind Russell, refuses to allow her beloved nephew to be molded into a stuffy elitist. Specifically, Mame does not want the young man to wind up like his soon-to-be-ex girlfriend, whom she refers to as an “Aryan from Darien.” Mame’s notorious slam of Darien followed an earlier and equally unflattering film portrayal of the town as close-minded and intolerant. Gentleman’s Agreement, starring Gregory Peck, referenced what was said to be an informal understanding among Darien property owners that no one would sell real estate to Jews.

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The big-screen depictions of Darien weren’t based on hearsay. Darien was known to be a “restricted” community, which was a fairly common phenomenon outside many major cities by the 1920s. Developers had figured out that promises of exclusivity drew buyers. Real estate advertisements freely used the term “restricted” as a selling point. An advertisement in the New York Times for a property for sale in South Norwalk, Connecticut, described a “Highly restricted desirable home at Harbor View Beach.” Another ad, for a Connecticut beach house overlooking a golf course, omitted the exact location but specified instead that it was a “restricted section.” The ads did not spell out the restrictions, but the implication was clear: the neighborhoods were “safe” for a certain class and color of people. Developers often spelled out the restrictions in covenants written into the property deeds. Early on, the covenants restricted the kinds of uses allowed on the property and set design and cost standards. Over time, however, restrictions were extended to exclude certain types of people, like the ban on Jews at the Noroton Neck beach.

After the term “restricted” went out of favor, Darien continued to uphold the sentiment. Loewen tells of a sign that was posted on Darien’s Hollow Tree Ridge Road during the 1940s that openly designated the area for “Gentiles Only.” As time went on, intolerance was broadcast in other ways. In the 1950s, for example, when an all-black church from Harlem expressed interest in buying a twenty-one-room Darien estate for use as a summer camp, the town quickly adopted zoning rules that made such a use impossible. In 1960, a Yale student reported that anti-Catholic pamphlets were being distributed at Darien’s Republican headquarters.

The truth is, Darien has never quite shed its pre-civil-rights-era reputation for intolerance. Certainly its demographics, which haven’t changed much since Coffin’s day, don’t do much to dispel the image.Even though the town is flanked by the very diverse cities of Norwalk and Stamford to its east and west, respectively, Darien remains the “whitest” suburb along Connecticut’s Gold Coast and, as of 2010, the wealthiest, with a median household income of $185,619.

How is it that Darien has remained so white and so extremely wealthy for decades? The usual answer to the question of homogeneous demographic makeup is that there is a natural sorting effect. Expensive, attractive suburbs draw highly educated, affluent people who demand high-performing schools and safe surroundings for their children. Though this is legitimate on the face of it, natural selection does not tell the whole story of the town’s homogeneity. History also has a lasting impact on the shape and tone of exclusive suburbs such as Darien. The homeowners of today who zealously guard their two-acre zoning are, whether they know it or not, perpetuating a pattern of exclusion laid down long ago.

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The needs of its own elderly population finally caused the town to lift its ban on apartments in 1983. A decade passed before a major developer, AvalonBay Communities, turned up. Avalon wanted to build a 189-unit development on thirty-two acres near the train station. A quarter of the apartments were to be affordable. The town’s response was hardly welcoming: saying they wanted the land for town amenities, officials took steps to repel the project by condemning the property. Voters ultimately derailed that strategy, however—they could not stomach the $27 million buyout price. Avalon built its project.

Today, whether homebuyers choose Darien for the waterfront, the school system, or the “people like us” factor, the town’s exclusivity cannot be solely attributed to individual preferences or the workings of the free market. History shows that Darien has actively cultivated and defended exclusivity as its “brand” for decades.

Certainly present-day Darien is not the bigoted place ridiculed in "Auntie Mame." Since 1981, the community has hosted a chapter of A Better Chance, which sponsors six inner-city students so they may attend Darien High School. The Avalon apartments were recently publicly praised by a top town official as “the best thing that’s happened to our town.” And in recent years, spurred by the Stefanonis and 8-30g pressures, a few people in town have worked tirelessly to build support for affordable housing. Notably, the Darien Housing Authority, after a years-long effort, has finally obtained financing and town approvals to redevelop and expand its tired rental housing, which dates to the 1950s.

“Most people living here now were born after 'Gentleman’s Agreement' came out and don’t even know about it,” says Evonne Klein, the former first selectman, who, it’s worth noting, was elected to her post with a Jewish name (her husband’s). “I don’t think the new generation is thinking that way.”

Still, Klein has acknowledged that as late as the 1990s, when she ran for the town’s board of education, she was advised to run under her maiden name, Gallucci, and she did—just that once. Even now, there are people in town, some in positions of power, who remain firmly committed to what Klein calls “protecting the brand.” The “unfortunate thing,” she goes on, is “when you have people who think a certain way and then they make proclamations in public, it doesn’t allow communities like Darien to shed the Gentleman’s Agreement reputation.

* * *

"While she was the first selectman, from 2003 to 2009, Klein pushed for action on affordable housing, partly because she had to: homeowners were demanding she do something to fend off the Stefanonis. One relatively easy change she supported was “inclusionary” zoning. Inclusionary zoning is common practice in the cities of Norwalk and Stamford, where it is seen as a painless way of continually adding to the stock of affordable housing. The policy is fairly simple: it mandates that all new market-rate developments must include a set percentage of affordable units.

Darien’s planning and zoning commission, under the watchful eye of chairman Frederick B. Conze, was not inclined to go along. A veteran member of the elected commission, Conze wasn’t a fan of affordable housing generally. He had once declared at a public hearing (to enthusiastic applause) that the problem with affordable housing is that “the people who are the neighbors around the project, they’re the ones who have to take the bullet.” He went on: “I have to honestly tell you that I look at this as a virus. That once you open this box, you never get it back into the bottle, because it will be replicated all the way around town.”

Nevertheless, in 2009, with the specter of Chris Stefanoni hanging about and after protracted debate, Conze and the commission signed off on a modest inclusionary strategy. The regulation they approved requires at least 12 percent of the units in new multifamily projects and subdivisions to be reserved for people earning no more than 80 percent of the state median income. In truth, the policy is unlikely to generate much affordable housing—because Darien is nearly built out, big projects are few and far between. Still, Darien’s approval of the policy seemed to mark a milestone for a town that hadn’t been proactive on the issue. A state housing organization said Darien deserved “five gold stars.”

What went largely unnoticed until several months later was that Darien’s “inclusionary” policy was actually kind of exclusionary. According to the language worked out by the zoning commission and town counsel, new affordable units were to be offered to a designated “Priority Population.” People who had dibs were listed in order of priority:

1. Darien residents who volunteer as first responders

2. Darien public employees

3. Darien residents who work in town

4. Darien residents

5. Nonresidents who work in Darien

6. Former residents who want to move back

7. All others

The list wasn’t unusual in the sense that policies granting housing preference to residents and town workers are fairly common. Towns understandably want to take care of people with ties to their community. Indeed, the need in their own backyards is often what prompts towns to pursue affordable housing on their own.

Residency preferences for workforce housing are not illegal, but at the same time, the preferences cannot be used as a way to keep out certain groups. The Fair Housing Act prohibits housing discrimination on the basis of a range of protected categories, including race, color, and national origin. And the US Department of Housing and Urban Development (HUD), as well as state housing-finance offices, has strict guidelines for the fair marketing of affordable housing to a range of potential applicants. Local preferences are typically allowed as long as they are implemented in a way that doesn’t have a greater impact on minorities.

Darien’s preference rankings were unusually lengthy. People from outside Darien were at the back of a very long line, a line in which even former Darien residents were allowed to cut in front. When asked for their perspective on the preferences, fair-housing experts suggested that, if not discriminatory in its wording, Darien’s policy held the potential to be discriminatory in practice. Diane Houk, then the executive director of the Fair Housing Justice Center in New York, told me for a story for the New York Times that she found the preferences to be “highly suspect” in a town that was 94 percent white. “If I were the town,” she said, “I would want to have an assessment done on what the impact will be.”

Darien officials seemed unconcerned—the preferences stayed in place. But about six months after the Times story, in May 2010, Darien’s newly elected first selectman, David Campbell, received a letter from the Civil Rights Division of the US Department of Justice. The department was opening an investigation into whether Darien’s zoning and land-use practices violated the Fair Housing Act. More specifically, investigators wanted to know why the town had adopted the “Priority Population” clause.

Word got out after DOJ investigators contacted the Stefanonis (who were happy to share information about the town’s reaction to their affordable-housing plans). Conze, who works in real estate, repeatedly denied any discriminatory intent behind the preferences. “The intentions by passing this were completely genuine, and were focused on a very specific need,” he said, referring to the housing-cost burden on existing residents, “and were not designed to be exclusionary but rather to address that specific need.” After meeting with DOJ investigators, however, Conze voted along with the rest of his commission to repeal the controversial language. In its place, a new requirement specifies that all affordable units “be offered for sale or rent in compliance with all applicable federal and state Fair Housing laws.” The amendment put the issue to rest. But the DOJ was now interested enough in Darien to keep its investigation open.

* * *

At the top of a narrow staircase, off a hallway crammed with kids’ sports gear, is what the Stefanonis call their “war room.” A small room lined with white wainscoting, it is bereft of décor. Two old desks face opposite walls—one for Chris, one for Peggy. Peggy’s is stacked high with files, as is much of the area surrounding her desk. Folders peeking out from boxes beneath are labeled “Slave Auction” and “Anti-Semitism.” Chris’s desk, on the other hand, is almost clean, save for several lists written in tiny script.

This is 149 Nearwater, about a half-mile up the road from the site of the Stefanonis’ first home, now the wildflower meadow. Some property owners have resisted selling to the Stefanonis, so in order to get this well-worn antique cape, the couple sent in Chris’s mother (now deceased) as a straw buyer. Outside, a stone wall runs along one edge of their 1.5-acre property, coming to an abrupt halt as it nears the driveway. Unused stones and pallets are strewn about the yard. Chris hired guys to build the wall but stopped when the town hassled him about it being too high in places. The same goes for the yard—he’s stopped mowing the lawn regularly. “This house looks like something in Appalachia,” Chris says gleefully. “Everything that blows in my yard, I leave it there. This is my protest.”

Darien, he says, has too many “bullies” who are used to getting whatever they want. He and Peggy are determined to give them a run for their money. Not surprisingly, they’ve made a few enemies in the process. After a local news affiliate interviewed them, a baseball dad they’d been friendly with e-mailed to say: “YOU BOTH SHOULD BE ASHAMED OF YOURSELVES OVER YOUR GREED, AND THAT IS WHAT IT IS ALL ABOUT. DO NOT EVER TALK TO ME AGAIN.” They routinely receive magazine subscriptions they never ordered. At their old address, their mailbox was bashed off its post. They had to call the police to deal with a neighbor who repeatedly honked his horn every time he drove by their house.

None of this dissuades them. It only bolsters their belief that they are the good guys in this fight. They are in perpetual litigation. Peggy spends so much time at a nearby law library that she has identified a “lucky desk.” They spent three years appealing the town’s denial of their second 8-30g application. This time they’d chosen what they thought was an ideal location: a half-acre lot across from the train station. But Conze’s commission still objected to the project’s density. In February 2012, after mediation talks between the two parties broke down, a superior court judge ruled in favor of the Stefanonis’ proposal for a three-story apartment house. The judge concluded that the town had “provided no evidence of the harm that will occur or why this harm outweighs the need for affordable housing.” Unwilling to give up the fight, the town had filed for appeal, despite the mounting legal bills.

* * *

Even as the moratorium controversy continued to play out, bold allegations of discrimination emerged. Conze and the town planning and zoning commission were the target of a federal civil rights action filed by a former resident who, like the Stefanonis, had tried to turn his house lot into affordable housing. Unlike the Stefanonis, after his application was denied, this resident, Christopher Hamer, didn’t have the wherewithal to fight for long. He was sued by neighbors who accused him of “blackmail,” had to pay a lawyer, and wound up bankrupt. Hamer was now accusing the commission of denying projects like his in order to keep out black residents.

Conze’s previous “virus” comment was cited in the complaint as proof of bias, as was his warning in a State of the Town address that the “demographic and economic forces generated by our immediate neighbors to our east and west cannot be taken lightly.” Hamer’s attorney, John Williams, argued that, given that Darien’s neighbors are the diverse cities of Norwalk and Stamford, Conze was clearly referring to African Americans. “He did everything but use the ‘N’ word,” Williams told a local reporter. Conze has declined to comment, but town counsel Fox has denied the allegations on his behalf.

Still, for all the controversy swirling around the actions of town officials, the Darien brand was showing signs of change. The public-housing expansion had broken ground. The US Department of Justice finally appeared satisfied: in the summer of 2012, after keeping an eye on the town for two years, federal officials announced they were closing their investigation.81 And the Darien Housing Authority had very quietly adopted an official policy for verifying incomes and maintaining the waiting list for Clock Hill Homes.

“One small step for us,” wrote the housing authority chair, Jennifer Schwartz, in an e-mail to her board. “One giant step for the town of Darien.”

Adapted from “Snob Zones: Fear, Prejudice and Real Estate“ by Lisa Prevost (2013, Beacon Press). Excerpted with permission by Beacon Press.