“It was pouring rain so we went to look at open houses as an activity,” she said. “We looked at a house on Fresh Pond Road, and my husband said, ‘I think we should buy it.’ I said, ‘Whoa, whoa, whoa — we don’t know anything about Sag Harbor!’” They ended up renting for a few years, then bought a post-and-beam kit house built in the early 2000s on Ferry Road and did a complete renovation.
They love the ubiquitous water views, of Gardiners Bay, Northwest Harbor, Sag Harbor Bay and Noyac Bay — which, Ms. Drackett pointed out, you don’t get in other parts of the Hamptons — and enjoy getting out on paddleboards and in boats, from which they can glimpse houses that look modest from the street but open expansively on the waterfront.
Ashley Anderson Nowak became a first-time homeowner when she and her husband bought a house in a wooded development north of the village. Ms. Nowak, a consultant who worked as a scheduler for President George W. Bush, chose the house because of its proximity to Foster Memorial Beach, known as Long Beach, where calm water and soft sand draw families with young children. Sagg Main Beach, on the ocean, is six and a half miles south.
The Nowaks, who have a 3-year-old son, are considering moving to Sag Harbor full time. “It’s a beautiful, vibrant year-round community with an amazing food and wine scene,” Ms. Nowak said. “I step out my door and I’ve got Channing Daughters and Wölffer and I’ve got two farm stands, I’ve got amazing restaurants in Sag Harbor. We’ve got that culture around us and we have a quiet place to have family time.”
What You’ll Find
Gray-shingled houses with roses climbing picket fences are what make the village picturesque, but those who prefer newer construction and more yard space will find it, particularly outside the village, in North Haven and Noyac.
“There is a whole new layer of ‘new old homes’ — new construction with every amenity built to architecturally reference Sag Harbor’s historic federal, farmhouse and Victorian architecture,” said Gioia DiPaolo, an agent for Douglas Elliman, adding that while prices have steadily risen, the low end is also robust.
A Bulova watchcase factory, shuttered in 1981, has been repurposed as condominiums and townhouses. Diane Saatchi, an agent for Saunders & Associates, said it had drawn buyers who owned houses south of Route 27, the main east-west highway, seeking to downsize but keep a place in the area.
What You’ll Pay
“Waterfront real estate accounts for the highest numbers in Sag Harbor Village, North Haven and Noyac,” Ms. DiPaolo said, adding that sales over the past year have been as high as $30 million.
The median sales price so far this year in Sag Harbor is $1.65 million, according to Saunders & Associates, and in the area excluding the village, $1.5 million.
Arts and letters run deep here. Canio’s, an appealingly ramshackle bookstore near the Whaling and Historical Museum, hosts an annual reading of “Moby-Dick.” John Steinbeck, E.L. Doctorow, Betty Friedan, the playwright Lanford Wilson and the artists Eric Fischl and April Gornik have all lived here. Colson Whitehead set his 2009 novel, “Sag Harbor,” in the traditionally African-American enclave of the village. The American Hotel, established in 1846, remains the doyenne of Main Street, with a clubby bar and dining room. GeekHampton, a sort of mini-Apple Store, can be found around the corner. The Bay Street Theater produces work by significant playwrights with well-established actors. Now playing: “Intimate Apparel,” by Lynn Nottage.
The biggest news of 2016 was the fire that destroyed the Sag Harbor Cinema, leaving a vast hole in the center of Main Street. The local newspaper, The Sag Harbor Express, reported that the popcorn stand in a new theater would be named for Billy Joel, a part-time resident and one of a handful of celebrity donors to contribute to the $8 million campaign to build a new cinema.
The Sag Harbor Union Free School District has 959 students. For 2016, 45 percent of the students in Grades 3 to 8 met state standards in English and 53 percent in mathematics, compared with 38 and 39 percent statewide, respectively. The graduation rate from Pierson High School is 89 percent. The average SAT score in 2016 was 1,586 of a possible 2,400 points.
From New York City, Sag Harbor is about two and a half hours by car, although in summer traffic it can take much longer. The Hampton Jitney stops in the village, but the closest stop on the Long Island Rail Road is Bridgehampton, a 20-minute drive.
According to the Sag Harbor website, when the village was a thriving whaling port in the 18th and 19th centuries, it “had more tons of square-rigged vessels engaged in commerce than New York City.” Early residents called the place Sagaponack Harbor, or the Harbor of Sagg.