Southold Real Estate

The town of Southold is in Suffolk County on the North Fork of eastern Long Island. Robins Island, Plum Island and Fisher’s Island are also part of the township. Shelter Island lies just to the south.

With a history that dates back to 1640 when it became New York’s oldest English settlement, Southold has a rich heritage immediately recognizable to modern visitors. Cutchogue is home to one of the best surviving examples of domestic English architecture in the United States.

Amid acres of farmland, well-kept historic homes provide an idyll for those interested in the natural beauty of the island rather than suburban life or summer hotspot revelry. Peconic—named for Peconic Bay and once home to Albert Einstein—was a noted artists’ haven in the early 20th century. The area’s beaches on Long Island Sound and Noyack Bay offer stretches of pristine sand.

In 1973, the first winery on Long Island was established in Cutchogue. The North Fork is known for its vineyards and wine culture, and wineries throughout the region are open year-round for tours and tastings.

Orient is the easternmost point on Long Island and one of the island’s most picturesque spots, with sparkling beaches and New England-style homes—many of which are seasonal vacation homes—spanning three centuries. Honeymooners often find an ideal romantic getaway spot here. The tiny village, whose population swells in summer months, relies on nearby Greenport for most of its commercial needs. Orient State Park offers swimming, boating, golf and fishing in addition to a rare maritime forest with red cedar trees, blackjack oaks and prickly-pear cacti.

Fishers Island, 11 miles from Long Island’s tip and within two miles of Connecticut, is another popular summer destination with a tiny year-round population.

Southold is accessible via the Greenport branch of the Long Island Railroad and major highways. The North Ferry crosses the Peconic Bay to Shelter Island from Greenport.