Greenport, N.Y.: A Casual Village on the Waterfront

Greenport, the mile-square waterfront village on the North Fork of Long Island, has had to reinvent itself numerous times since its days as a 19th-century whaling port. Necessity struck again this year with the coronavirus pandemic, which tested the resilience and adaptability of a local economy that relies on a seasonal influx of visitors, and wound up fueling an already heated real estate market.

“Even in the spring, when we couldn’t show a house or tour a house in person, there were bidding wars,” said Sally Heitel, an agent who manages the Greenport office of Century 21 Albertson Realty. “Houses are closing at asking price or above.”

The rental market was particularly tight this year, she added, because people who normally rent out their homes for at least part of the summer stayed put.

Walkability, varied and historic architecture, harbors, convivial restaurants, bars and shops, and convenient transportation have long made Greenport a hub for weekenders and vacationers, particularly those who prefer its more casual feel to the ever-ritzier and traffic-choked Hamptons. On quiet residential streets, instead of formidable hedges you’ll see roses and hydrangeas growing over picket fences in front of shingled saltboxes and farmhouses with generous porches.

Joanne Greenbaum, an artist based in Manhattan, rented places in Greenport for several years. “I wanted to have a place to go when I’m an old lady,” she said. “Wait, I’m already an old lady!” (She’s 66.)

In May, Ms. Greenbaum bought a newly renovated four-bedroom, one-and-a-half-bathroom farmhouse on Sterling Place for $580,000, with a separate two-car garage. “I’ve basically turned the whole house into a studio,” she said. Even the garage is set up for painting and sculpture.

She’s not ready to abandon the city completely. “You have to show your face in the art world,” she said. “But I love it here. It’s quiet. I go to the beach. I walk my dog into town to get a coffee. I’m working well. The casualness of Greenport is totally up my alley. People are neighborly, but there isn’t a scene. You can choose to be social or choose not to; you won’t be judged.”

Ms. Greenbaum prefers the small-town feel of Greenport to the open spaces she might have found elsewhere. “Even though I live alone, I don’t feel alone,” she said. “I like it that there are people around, and I like that it’s a diverse community.”

Jill Dunbar, an agent in the Greenport office of Douglas Elliman and a former owner of the Greenwich Village bookstore Three Lives & Company, moved to Greenport about 30 years ago. “The town was a bit down and out, rough around the edges, but people were welcoming,” she said. “Then the New Yorkers moving here were from Greenwich Village. Now they’re from Brooklyn.”

Greenport is interesting in its blend, she continued, with its long-established Black community, continuing waves of immigrants — Greek, Mexican, Guatemalan, Colombian — and the influx from the city. “The infusion of new energy and creativity is thrilling,” she said.

Longtime North Forkers are vital to the mix. At the Halyard, the restaurant at the Sound View motel with highly Instagramable sunset views, the locally sourced menu is the work of Stephan Bogardus, the young executive chef, who grew up in nearby Mattituck and was formerly the chef at another local favorite, North Fork Table & Inn, in Southold.

The village of Greenport, on the banks of the Peconic River, is a North Fork headquarters of sorts for those in pursuit of serious local food and wine, fishing, gardening, beach-going, water activities, bicycling and bird-watching (there’s an Audubon Society). Beaches are plentiful along the river, which flows west from Gardiners Bay and surrounds Shelter Island (a 10-minute ferry ride away), and north across Route 48, on Long Island Sound.

Part of Southold Town in Suffolk County, Greenport, with a population of about 2,200, is incorporated, and offers municipal services like water, sewers and brush pickup. There’s a 70-bed hospital and a beloved public library. Greenport West, a 3.3-square-mile census-designated place with a population of about 2,100, surrounds the village on its three landward sides.

Greenport was laid out as a working-class enclave in the 19th century, so residences are on small lots, rarely bigger than a quarter or half acre. Gracious Victorians, farmhouse fixer-uppers, two-family clapboard dwellings, beach cottages and an increasing number of waterside condos make up the housing stock.

Greenport West has more typically suburban homes, as well as a couple of vineyards and farms. Vineyard View, 50 newly built units of much-sought-after affordable housing, will be filled through a lottery system (a first round was scrapped after it was determined that not all applications had been included in the draw). Peconic Landing, a 144-acre retirement community, includes private beachfront on Long Island Sound.

As of Sept. 11, there were 28 residences for sale in Greenport, including single-family homes, multifamily homes, condos and co-ops — about half the usual inventory, Ms. Dunbar said. Current listings range from a 650-square-foot cottage for $215,000 to a grand waterfront house for $2.75 million. Of the other available listings, three are multifamily homes, one is operating as a bed-and-breakfast, and one is a restored church.

In the past 12 months, sales of 69 residences have closed in Greenport, Ms. Dunbar said, citing figures from One Key Multiple Listing Service. The numbers reflect a year in which there was very little activity for six months, she noted, although sales picked up in July, once Phase 4 of Suffolk County’s reopening began. Of those residences, 56 were single-family homes with a median sale price of $633,000; 12 were condos or co-ops with a median price of $385,750. One multifamily house sold, for $540,000.

In the previous year, sales of 66 residences closed. Of those, 51 were single-family homes, with a median sale price of $690,000. Four multifamily homes sold, with a median price of $797,500; 11 condos and co-ops sold, with a median price of $405,000.

While in the past it was possible to find a year-round rental for as little as $1,200 a month, this year they are scarce, and priced at $2,000 or more, Ms. Heitel said.

“Part of what’s funky and neat about the village is that it’s got its own little government,” said Bridget Elkin, an agent at Daniel Gale Sotheby’s who moved to Greenport five years ago after living in San Francisco and New York City. She and her husband, Eric, have a 15-month-old daughter, and were part of a successful push to get the village speed limit lowered from 30 to 25 miles an hour.

The Art Deco movie theater on Front Street used to be open only during summer months until Lisa Gillooly, an agent for Corcoran, and her partner, Tony Spiridakis, a writer for film and television, made an arrangement with Josh Sapan, the chief executive of AMC Networks, who bought and restored it as a labor of love. Mr. Sapan agreed that they could show movies there for free on winter weekends, if they could figure out how to get the ancient heating system working (they did). They also took charge of making popcorn for cold-weather crowds and changing the letters on the marquee. For now, the letters spell Greenport/Six Feet Apart/Standing Together.

That D.I.Y. ethos has been in high gear in recent months. Although the antique carousel in Mitchell Park is silent and the Monday night summer dance parties with live music are on hold, the village has created parklets on its two perpendicular commercial streets, Main and Front, where restaurants and shops have set up tables and awnings. Restaurants like Claudio’s (which caters dockside to the boating crowd), 1943 Pizza Bar and First & South have devised inventive systems for takeout food. Beall & Bell, a popular vintage furniture store in a former Masonic temple, is selling its finds on Instagram.

North Fork Yoga Shala, usually upstairs from Beall & Bell, is holding distanced pop-up classes in grassy yards and on the deck of the Menhaden, the fancy new hotel in town. Shops like Greenport Wines and Spirits, which carries many local wines, and the independent Burton’s Bookstore made deliveries until they were able to open to masked customers. Clarke’s Garden and Home set up an honor-system box in its courtyard.

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