Southold attracting homebuyers to its North Fork beaches, wineries, restaurants

The Southold Town Board recently tweaked legislation to permit construction of affordable rental apartments in existing structures, and approved a 15-unit affordable rental development next to town hall, says Southold Town Supervisor Scott Russell.

The board is also drafting a law that would prevent overly large mansions from going up. “The basic premise of the law is to right-size the limits to the parcel size itself,” Russell says.

Housing prices, which have risen significantly lately, have made the community out of reach for many, while at the same time, local marinas, restaurants and other businesses have seen a boost. The area is attracting many second homeowners, as well as retirees and those working remotely.

There is a large number of vintage Colonials and Victorians, with prices starting at $700,000 for a fixer-upper, going up to $3 million for a four-to five-bedroom waterfront house with sizable acreage.

Southold’s popularity has created some headaches, including an increase in traffic, especially during pumpkin picking and other fall events. “It’s definitely at a crisis level, and the public’s frustration with it is at a fever pitch,” says Russell, noting that with only two roads going through the hamlet, it’s a very difficult issue to resolve.

Main Road is home to restaurants, antiques and other shops. Vineyards and farmstands are plentiful in the area, and there's also a fish market, an oyster company and Horton Point Lighthouse, which has commanding views of Great South Bay and a nautical museum.

One noted summer visitor was Albert Einstein, who made friends with the owner of Rothman's Department Store in 1939. Today, Einstein Square, a gathering spot, is on the site of the shop.

While Southold attracts many visitors in the summer, “It’s also a fabulous year-round community,” says Barbara Poliwoda of Douglas Elliman Real Estate, a resident of the hamlet, adding that there are family-friendly activities throughout the year.

At 4,000 square feet, this postmodern five-bedroom, 4.5 bath house built in 2019 features a front porch, open floor plan, chef’s kitchen with a service window to the patio and butler’s pantry, hardwood floors, bay windows, built-ins and a ceiling-high stone hearth in living room. Formerly a horse property, the 2.44-acre parcel has an outdoor kitchen, swimming pool, hot tub and barn. Taxes are $24,804. Thomas McCarthy, Thomas J. McCarthy Real Estate, 631-765-5815.

Built in 1927, this 1,600-square-foot shingled cottage near Horton Point Lighthouse with beach rights has three bedrooms, two bathrooms, beamed ceilings, original fieldstone fireplaces, and a sunporch/dining room. The 0.66-acre property has a pool, outdoor shower and landscaped grounds. Taxes are $6,752. Sheri Winter Parker, Corcoran Group, 631-765-1300.

This updated 1,600-square-foot Cape built on a ¼-acre lot in 1950 with Sound and bay beach rights is near Southold Bay and Peconic River. It has an open floor plan with three bedrooms, two bathrooms, stainless steel appliances in the kitchen, hardwood floors, first-floor primary suite, and second-floor office space. Taxes are $6,095. Barbara and Kenneth Poliwoda, Douglas Elliman Real Estate, 631-477-2220.

N. Bayview Rd.

N. Bayview Rd.

Main Bayview Rd.