Nissequogue and Head of the Harbor, side-by-side villages in central Long Island with woodsy waterfront not far from strip malls and interstates, can seem to be hiding in plain sight.
“A lot of people think Long Island is all about tract development from the 1950s,” said Anthony Coates, 59, a financial adviser who is a resident. “But my experience has been much different.”
In fact, the landscape — with its shady coves and sandy spits, and houses grizzled by weather — can seem more New England than New York, said Mr. Coates, who grew up in nearby Stony Brook and lived in Stonington, Conn., before returning to Long Island.
Mr. Coates’s most recent house, a four-bedroom whose oldest section dates to 1791, takes advantage of that shoreline with its perch on the Mill River, with sweeping water views from many windows. Mr. Coates, who bought it for $615,000 in 2016, sold it this month for $665,000 after marrying Cleo Beletsis, also a financial adviser, so the couple could move to Indian Wells, Calif., near Palm Springs.
But the desert won’t replace the dunes for long. The couple own a pair of properties in Nissequogue, overlooking Long Island Sound, where they plan to build a summer home.
Residents can be a bit defensive about Nissequogue, which is often confused with Quogue, the Hamptons getaway. But while both appear to be named for the Nesaquake, a Native American tribe, Nissequogue is about 30 miles closer to the city and has more of a year-round population.
The villages are also not on many beaten paths. Windy roads — some no wider than hiking trails, and many dead-end and private — seem to discourage visitors, although those who stumble upon the secreted-away neighborhoods can find themselves smitten at first sight.
A few years ago, Manhattan residents Susannah Charbin and her husband, Adrian Charbin, were spending a lot of their free time in East Hampton, where Mr. Charbin’s father lived. The couple considered getting a weekend retreat nearby, but the long trip back and forth to the city seemed daunting while both had full-time office jobs.
Seeking a second home with a shorter commute, the Charbins started exploring other areas on long, looping North Shore drives. In Nissequogue, they happened upon a two-bedroom 1920s fixer-upper, but only because they took a chance on a street called Jack’s Path, which shared a name with their Maltese-mix dog. “I know it sounds corny, but we took it as a sign,” said Ms. Charbin, 33, who owns a digital marketing firm that works with design companies.
Today, the couple, who have a 4-year-old daughter and a 2-year-old son, are on their second home in the area, a midcentury-modern house on the Nissequogue River. The house, which had four bedrooms when they bought it, now has five, after a renovation that added a new wing. In 2017, it cost “under $1 million,” Ms. Charbin said.
Along the way, the Charbins ditched their Manhattan apartment to live full-time in Nissequogue, where they often work from home. Moving has allowed for some very nonurban activities. This month, Ms. Charbin plans to learn how to ride a horse, courtesy of a stable around the corner.
“It’s a lot wilder here than you think it’s going to be,” she said. “And the landscape has a lot of romance.”
What You’ll Find
Part of the town of Smithtown, Nissequogue and Head of the Harbor cover seven square miles of land and another five square miles of water, creating a nautical feel. But thick stands of tulip and maple trees blanket the terrain, so many houses are nestled in the woods.
With 3,037 residents between them, according to census records, Nissequogue, founded in 1926, and Head of the Harbor, in 1928, are basically mirror images. Both have mostly two-acre zoning, resulting in generous buffers between homes and a rural look. Both also tightly regulate fence heights and tree pruning, and for-sale signs with logos are forbidden. Single-family houses are the rule; there are no multifamily dwellings or businesses.
Many houses belong to small homeowner associations, which maintain the stairs that descend bluffs to beaches, and take care of plowing.
The Gilded Age can seem alive and well here. Majestic 19th-century houses with fireplaces big enough to stand in try to hide modestly behind hedges. Relatives of their 1800s builders occasionally live inside. But what’s left of some once-grand estates are only mysterious stone walls. Scattered throughout the villages are 1960s colonials, 1980s contemporaries and a split-level ranch or two.
What You’ll Pay
In mid-September, a total of 31 houses were for sale, with an average list price of $1.7 million, according to information from Douglas Elliman. The least expensive was a four-bedroom 1960s house on about two acres in a homeowner association in Nissequogue, for $699,000. The most expensive, also in Nissequogue, was a six-bedroom 2011 Mediterranean-style house with a guest cottage, on four and a half acres, for about $7 million.
Sales are up, but prices have dipped. Since January, there have been 26 sales, for an average of $1.13 million, according to Douglas Elliman. During the same period in 2019, there were 20 sales, for an average of $1.27 million, a decline of about 11 percent.
“What’s the scene? Napping, beach walks and cooking,” said Mickey Conlon, 44, a New York-based real estate broker who bought a Long Island Sound-facing weekend home in 2012, with his business partner and husband, Tom Postilio, 50.
The house — a Mediterranean-style place on more than two acres, with steps to a quiet, pebbly beach below — cost $870,000. But it had structural problems, Mr. Conlon said, so the couple razed it and built a similar one, with five bedrooms and eight bathrooms (three of them half bathrooms).
Mr. Conlon and Mr. Postilio, who grew up nearby, have been promoting the area as a mellower Hamptons, where comparable properties can be a third of the price. “When you grow up in a place, you take it for granted. But after you have been around the world, you see it through a different lens,” Mr. Conlon said. “Now I think it’s one of the most beautiful places I’ve ever seen.”
Lake Avenue, in the next-door village of St. James, has a string of modest, un-Hamptons-like restaurants. But entertainment often consists of walks, whether at the 216-acre Avalon Nature Preserve or the 125-acre David Weld Sanctuary, a former cattle farm.
Bookending the area are Short Beach and Long Beach, two parks for Smithtown residents. Admission is free but requires a parking pass. Long Beach is livelier, with some outdoor concerts.
Most students attend St. James Elementary School, which offers kindergarten through fifth grade for 520 students just outside the villages. On 2018-19 state exams, 57 percent of students met standards in English, versus 45 percent statewide; 69 percent met standards in math, versus 47 percent statewide.
From there, students attend Nesaquake Middle School for sixth through eighth grade. On 2018-19 exams, 59 percent of students met standards in English, compared with 45 percent statewide; 54 percent met standards in math, compared with 47 percent statewide.
Smithtown High School East, with 1,600 students, has a 97 percent graduation rate. On 2019-20 SAT exams, students averaged 586 in evidence-based reading and writing, and 590 in math, compared with 528 and 530 statewide.
Two Long Island Rail Road stations are close, St. James and Smithtown, on the Port Jefferson Branch. From St. James, there are five trains to Pennsylvania Station on weekdays between 6 a.m. and 8 a.m., with two running direct. Travel times are up to an hour and 40 minutes. Monthly passes are $405.
Commuters who prefer to drive often time their trips for when traffic on the Long Island Expressway is light. Under ideal conditions, Midtown Manhattan, 52 miles away, can be reached in an hour and 15 minutes, but it can take more than two hours.
The pandemic, however, has more residents shifting to telecommuting. Michael Utevsky, 71, is a lawyer who has made an office, with Stony Brook Harbor views, out of a bedroom in his 1830s farmhouse. As Mr. Utevsky said, “Life is just easier here.”
Box Hill, an estate on Moriches Road, was the summer house of Stanford White, the Beaux-Arts architect whose wife was Bessie Smith, a descendant of Smithtown’s founder, Richard Smythe.
White’s gabled, stucco-walled house, designed in 1885 and incorporating a shipbuilder’s house, is part of a small National Register district. He was introduced to the area by his partner Charles McKim, who designed a nearby estate, By-the-Harbor, said Leighton H. Coleman III, the villages’ historian, whose own house, built around 1770, once belonged to a ship’s captain.
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