Nassau Point

The North Fork of Long Island has the distinction of being the sunniest place in all of New York state. This tends to make people on this part of the island more rooted to the land than in the South Fork where the posh go to party. Whether they’re part of the local wine or agriculture industry or just helping to support their neighbors by buying local meat, dairy and produce at one of the many weekly farmers markets, there’s a connectedness residents feel to the hilly, rural landscape. This feeling has forestalled much development. “During COVID, this area didn’t see the same escalation as the South Fork,” says Carol Szynaka, an Associate Broker for Daniel Gale Sotheby’s International. “It’s one of the few areas where people don’t feel you have to have a lawn, so it feels more rural.” The Southold government runs a program through which financially burdened farmers may sell land to the town, which in turn keeps it free from residential development. The mellow and open character of these North Fork farming hamlets on the sea has led to a trope about the area: The North Fork is what the Hamptons used to be.

Because of the North Fork’s increasing popularity, inventory in places like Nassau Point is lower than it was 10 years ago. This has driven up costs. Today, at the bottom of the market you can find rustic two-bedroom and two-bath prewar Cape Cods on wild, sprawling lots for under $600,000. For $100,000 more, you’ll find historic well-maintained Victorian homes with three bedrooms and two baths on quarter-acre lots near small village centers. At the higher end of the market, postwar ranch houses with brightly painted shingles and three bedrooms on half-acre lots within walking distance to the Long Island Sound are listing for under $1 million. Under $2 million will buy you a landmarked Victorian with four bedrooms and its own library or a newly constructed millennium mansion with similar specs in one of the area’s rare housing developments. At the top of the line, palatial contemporary modern homes with infinity pools and up to seven bedrooms are listed for under $6 million. A new sustainable development called Baiting Hollow was recently constructed using environmentally friendly materials, a practice that is increasingly popular on the North Fork, says Szynaka.

Life in Nassau Point is slow and the recreational amenities reflect that. Many residents enjoy boating or watersports. There are parks with beaches along the eastern shore where people may swim in Peconic Bay and along the western shore skirting the sound. These parks are often limited to residents of corresponding villages, but all residents can access Suffolk County parks and beaches, of which there are many. The Old Cove Yacht Club is a volunteer-run club on Peconic Bay whose mission is to bring sailing to the public. A relatively affordable membership gives access to a comprehensive youth sailing program, among other things. The North Fork Country Club has an 18-hole golf course along with an active tennis program. Local wineries such as Pellegrini Vineyards offer tasting rooms where visitors can sample local varieties. “The farm to table movement is still important here,” says Szynaka, “and that includes the vineyards.” Karen’s Country Delicatessen can compete with the best delis in New York City and that’s important considering many of its customers are from Manhattan or still regularly commute there. North Fork Donut Company is a local favorite for its innovative treats and Legends Restaurant offers guests a classic Italian seafood menu in an upscale atmosphere.

There are two school districts in greater Nassau Point. The Mattituck-Cutchogue Union Free School District received an overall grade of A on Niche and its teachers and workplace environment are ranked in the top 10% of the state. The district’s Cutchogue East Elementary School received an 8/10 overall and a 10/10 for student progress on Great Schools. The Southold Union Free School District received an overall grade of B from Niche with an A- for its college preparatory curriculum. Southold Junior/Senior High School earned a B+ from Niche and has an excellent student-teacher ratio of 10:1. With the island of Manhattan just over two hours away by car, bus or train, Nassau Point is convenient for hybrid workers and part-time commuters. Whether they come for the wine, the water or the easygoing lifestyle, people tend to stay in Nassau Point.

Written By

Abbot Street

Photography Contributed By

Anthony Costa

Video By

Alexander Wong