Get to know Greenport

Compared to its more pastoral North Fork neighbors, this picture-perfect seaside village can feel like the life of the party. Greenport carries name-brand recognition for all who venture out east. It’s lively and thriving yet maintains an unmistakable laid-back appeal. Maritime endeavors have defined Greenport’s existence, as the village made its marks in whaling, shipbuilding, and other waterborne industries. In 1844, Greenport became the eastern terminus of the Long Island Rail Road, which operated through service to Boston via ferries to Connecticut from its deep-water docks. Today's harbor welcomes mostly recreational vessels, along with the North Ferry to Shelter Island. Over 250 buildings — dating as far back as 1750 — comprise Greenport’s historic district, displaying an impressive chronology of American residential architecture, including Italianate, Colonial Revival, and Bungalow-style homes. Exacting guidelines keep these eye-catching structures timeless throughout generations of Greenport residents and visitors.

Nearby Neighborhoods:

Get to know our homes for sale in Greenport

You can also check out our homes for rent in Greenport

Greenport Commerce & Culture

While you could spend days simply reading the historic plaques, there is much more to the Greenport experience. Head to Mitchell Park near the waterfront for attractions that include a bustling marina, an ice skating rink, an antique carousel, and ample lawns. During Prohibition, rum-running and speakeasies were vital to Greenport’s economy — residents knew the waters so well they could smuggle anything without detection. Nowadays, alcohol plays a far more licit role in bolstering this village with beloved craft breweries, distilleries, and wineries. There’s farm-to-table cuisine, a historic waterfront restaurant with centuries of provenance, happening spots featuring seasonal menus, and — of course — delectable seafood. Front Street and Main Street run perpendicular to each other and house much of Greenport’s commerce, from shops selling furniture, books, and vintage clothes to an Art Deco movie theater. Ferry service can connect you to the enchantingly idyllic Shelter Island in under 10 minutes.