Essex Road Was Built For Nantucket's Working-Class. Now It's Out of Reach for Most of Them

No street on Nantucket evokes the image of a working-class, year-round neighborhood in quite the same way as Essex Road. In the years after the neighborhood was built in the mid-1990s, Essex Road was an affordable oasis in a sea of increasingly expensive homes, a place where Nantucket’s workers and professionals could still buy into the island and hang their hats. But the island’s real estate boom has changed that equation.

Today, houses on Essex Road are selling for well over $1 million. Roughly half of the neighborhood’s land owners don’t actually live on the street, and there are even a few properties on Essex being offered as short-term rentals. While still home to many year-round residents as their primary residence, a red-hot Nantucket real estate market has priced families out of Essex Road, and prompted businesses and others to target the neighborhood for rental housing and staff quarters.

“Nothing on our street has sold for under $1 million in the last year or so, which is unheard of for our street,” said Allyson Bold, president of the Essex Road Homeowners Association, who bought into the neighborhood with her husband David seven years ago. “Our street was the place a family could come in and buy a starter home, and that’s just not the case anymore.”

The median cost of a lot on Essex between 1998 and 2000 was $115,000, about $207,000 in today’s money, adjusting for the higher inflation rates experienced by housing as compared to other goods in the United States. In contrast, the median home price on the island in 1998 was $673,000—585 percent higher. But in the last five years, the median price of a house on Essex Road has soared to $1,047,500, an increase of 505 percent over even the inflation-adjusted numbers from the late 1990s. And this is despite numerous subdivisions that have sliced Essex properties into ever smaller chunks. A house on Essex is still much cheaper than the Nantucket average of $2.8 million, but even so, it has moved out of reach for the average year-round Nantucket resident. For some Essex Road residents, this endangers the very qualities that made it attractive in the first place.

“We enjoy living in a neighborhood where we know people and kids are playing in the street, and [we enjoy] knowing all your neighbors,” said Heather Stevens Woodbury, an Essex homeowner and co-owner of Wicked Island Bakery who noted that real estate prices have prompted some longtime neighborhood residents to sell.

"We could sell right now, go retire and be done, but my kids would kill me,” Woodbury said with a laugh. “If people with a lot of money are buying [homes on Essex], you end up not knowing any of your neighbors and we might as well be a summer neighborhood."

Nantucket real estate broker Gary Winn, who worked on the development of some units on Essex Road in the mid-1990s, said that the neighborhood was built with the intention of it being a working-class neighborhood for islanders.

“When we said we were going to do this, we said we would make it...for year-round residents,” he said. “They would really be the least expensive units on all of Nantucket. All those duplexes we built as not low-income housing but as sort of affordable housing because there was a big need for it.”

And that’s what it was. While Essex Road was not officially an affordable housing project, and there were no restrictions on who could live on Essex or how much the homes could be sold for, initially almost every home was either owned or rented by a year-round, middle-income Nantucketer. According to Winn, this was still true in the late 2000s, when the Great Recession reduced the cost of housing and some lots on Essex even stood empty.

If any area of the island was going to stay affordable, it seemed likely it would be Essex.

But no area of the island has truly stayed affordable without deed restrictions or other mechanisms to control pricing. The percentage gap between the median home price on the island and the cost of a home on Essex has plummeted. Now, the median Nantucket home is only 267 percent more expensive than the median Essex home—over 300 percent lower than in the late 1990s.

In 2021, the sale of 4 Essex Road set a road record when it closed for $1.22 million. The next year, 21 Essex shattered that record, selling for a staggering $1.88 million. Now, 34 Essex is listed even higher, at $1.99 million.

In 1999, $2 million would have been enough to buy 17 houses on Essex Road, with money left over. 

Multiple Essex homeowners acknowledged that if they were looking to purchase a house today, the road they live on would be out of reach.

“It doesn’t surprise me, given what the market is today,” said Tucker Holland, Nantucket’s housing director.

“The chasm between what is affordable here and what is available is widening,” agreed Penny Dey, the president of the Nantucket Association of Real Estate Brokers (NAREB) and chair of the Nantucket Housing authority. “Last year, there were 37 sales on Nantucket under 500,000. Some were just land. Some were covenant houses and stuff. This year there were only seven.”

The truth is as painful as it is simple: there is almost nowhere on the island where the average family or individual can afford to buy a home.

And it is not just the cost of Essex that has changed. Twenty-six percent of homeowners on Essex list their primary residence as off-island, and another 25 percent live at a different address on Nantucket. Most of the homes on Essex Road that have left island hands have done so since 2012.

“That’s what happens,” Winn said. “It is, I guess, turning into more of a summer community.”

Some Essex homes are owned by real estate investors who control large numbers of properties. Gideon and Geoffrey Platt, affiliated with LLCs (limited liability companies) that own 28, 36 and 51 Essex Road, are also affiliated with a network of LLCs stretching across that island that, in total, control at least 24 properties. Another seven homes on Essex are owned by LLCs or individuals with at least four additional properties. Most of these are not based on the island, and in many cases, have converted their homes into dormitory-style rental properties where several renters pay for as little as a single room.

“Essex, in a way, has turned into more of a rental pool,” said Julia Lindner, executive director of the political advocacy group ACK•Now.

Businesses rent some Essex homes to employees, and some housing advocates see this as a problematic model. When someone’s housing is dependent on their employer, it can be nearly impossible for them to leave their job while staying on the island —even if they are being mistreated.

“Right now, the houses being sold on our street are not to single people or families,” Bold said. “That’s what we’re seeing. It’s increasing the traffic on our road, the on-street parking on our road. It’s causing a lot of congestion. We’re just not seeing as many families as we have in the past.”

Gaven Norton and his wife Sabrina – both Nantucket natives who grew up on the island – are among those who find themselves priced out of neighborhoods like Essex Road that were previously within reach. Just before the COVID-19 pandemic, Norton said they made an offer on an island home, only to find another buyer had swooped in with a higher, all cash offer. Then, the same thing happened again.

“We said ‘how does this keep happening?’ and that was the beginning of it,” said Norton, the owner of the ACK Surf School. “The next thing you know, the real estate market seemed like it went up 200 percent, then 300 percent.”

Discouraged by the real estate market, Norton and his wife are now looking for rental housing, while keeping an eye on any potential opportunities to buy their first home.

“We’re still looking, but what’s out there, even for something at $1 million, it needs a lot of work,” he said. “It’s definitely hard. If Sabrina and I – both born and raised here with families here – can’t find something, how are people finding housing?”

Some involved in the island housing arena question the very concept of affordable housing - at least how it’s technically defined in Massachusetts.

“I love that people talk about affordable housing, but that’s actually a technical definition from the state,” Lindner said. “We need to talk about year-round housing, about workforce housing.”

In Massachusetts, affordable housing is usually defined as and restricted to residents who make less than 80 percent of the area median income (AMI), adjusted for family size. But in some of Nantucket’s existing and planned affordable housing developments, that limit has been extended to include residents who make up to 150 percent of the area median income. This was done in recognition of Nantucket’s unusual circumstances: residents often earn too much income to qualify for affordable housing under the state definition, but not enough to actually afford a mortgage on a piece of island real estate. But there are still many island families and professionals whose income is beyond that 150 percent AMI threshold, yet are still priced out of the real estate market. This is what housing advocates have termed the ‘missing middle.’

Of course, it isn’t just the missing middle that is suffering.

Step into enough homes on Essex, and it is impossible to not see the blankets stretched across living rooms that divide beds and the tents leaning against trees in backyards. Often, the people living in these homes don’t speak English, or if they do, they aren’t willing to talk to unexpected visitors.

“They move into conditions like that because there is no other option,” Lindner said.

Everyone on Nantucket knows there is a problem - the island’s affordable housing issue has been discussed for decades. But in recent years the accelerating real estate market has prompted the town and voters to allocate significant resources toward what many believe is now a crisis.

“Generally, today, you can’t live here and not be aware of the issue and not have it touch you directly or a family member or a good friend, I just don’t think it’s possible,” Holland said. “Even folks who weren’t so supportive of the effort five years ago now understand that it is an existential issue for the community.”

However, efforts to solve the problem face two major obstacles. First, Nantucket is years behind. When even the most affordable neighborhoods - like Essex Road - are out of reach for year-round residents, the problem has gotten out of hand, and new affordable housing developments take years of planning, permitting, and coordination before construction can even begin.

“Certainly, the need for year-round housing has been known here for decades...but up until relatively recently, the town and the community had not really put a lot of effort into this area,” Holland said. “We are undoubtedly playing catch up, and things can’t happen as fast as anyone would like. There’s no magic wand you can wave and boom, housing.”

Second, every proposed solution is complex or controversial - usually both. Holland and other island housing advocates have long championed the idea of a community land trust, where the trust would purchase the land a house is on, and middle-income homebuyers would only pay for the building.

To fund the land trust and other potential housing initiatives, Nantucket housing advocates support a 0.5 percent real estate transfer fee on property transactions over $2 million, which would have added up to $5 million in revenue last year alone. Nantucket has voted in favor of the so-called “housing bank” legislation at every Town meeting since 2016, but powerful opposition from the Massachusetts Association of Real Estate Brokers has stymied efforts to get it approved at the State House in Boston.

Lindner, however, doesn’t think the transfer fee is necessary. Instead, she suggests fundraising. “How else did we get conservation land? How did the Nantucket Conservation Foundation amass all that land?” she asked.

Frustrated, Lindner feels the Town isn’t doing enough. “We’ve authorized millions and millions and millions of dollars, but if I was looking for a house, I would be discouraged,” she said. “We’re appropriating a ton of money, and we’re not seeing any progress.”

“We’re using all of the tools available to us today, but they simply aren’t enough,” Holland countered. “A challenge is a reliable ongoing source of revenue, which is what the transfer fee would provide.”

Other solutions are even more controversial. Some 40B developments that dedicate a percentage of their housing units as affordable have generated intense pushback. Perhaps no development exemplifies that better than Surfside Crossing.

A 156 condominium unit development, Surfside Crossing has been criticized as too dense, too large and poorly located. Proposed by developers Jamie Feeley and Josh Posner, Surfside Crossing’s 156 condos would be contained within 18-three story buildings (two stories above grade) on 13 acres of undeveloped pine forest off South Shore Road. Twenty-five percent of those units would be deed restricted for affordable housing, or a total of 39 units within the development.

Opponents also argue that since 75 percent of the condos are not restricted as affordable units , they will likely become investment properties or short-term rentals — perhaps the most controversial topic in the entire housing debate.

Even Essex Road now has three active short-term rental properties, and the island has over 2,000. Lindner and ACK•Now argue these short-term rentals can take homeownership opportunities away from year-round residents and should be regulated.

Lindner and ACK•Now support locals and second homeowners renting their homes on a short-term basis for part of the year, but want to restrict investor-owned short-term rentals.

“I think the majority of people believe that commercial short-term rentals don’t belong in year-round neighborhoods,” she said.

ACK•Now’s position, however, has been viewed with skepticism by many on Nantucket, and its first Town Meeting warrant article in 2021 was defeated by a wide margin. The organization has been accused of being elitist, radical, uncompromising, and sensational.

“There is a narrative that has been created in the last two years that has not been based in factual information and it has inflamed the dialogue,” Dey said.

She argues that corporate investors don’t account for a meaningful chunk of short-term rentals on the island and does not see short-term rentals as a major concern.

“Short-term rentals are a symptom. Short-term rentals are not the problem,” she said.

Underlying the entire debate is a sense that Nantucket simply does not have the space for the number of people who want to live here.

“Eventually, we’re going to have to talk about capacity,” Dey said. “Who gets to live here? Who doesn’t? This capacity conversation has to happen at some point.”

“Some folks say we just need a bigger boat, but that’s waving the white flag,” Lindner said. “Once we have a commuting workforce, once our teachers and firefighters live on the other side—and it has already started, the writing is on the wall—then the soul of Nantucket is gone.”