Greenport isn’t exactly undiscovered—its wineries have been successful for years, and it’s a go-to for carless New Yorkers because it’s walkable and close to the train. But it’s also not a circus like the Hamptons on a busy Saturday afternoon. Instead it’s “still an area where you can get value,” says Corcoran’s Ernie Cervi. For instance, a three- or four-bedroom on the bay in the Hamptons would fetch $60,000 to $75,000 for the season. In Greenport, it’d be more like $40,000: still a lot of money, to be sure, but split it with another tenant or two, and it starts to sound achievable. The long-discussed ferry service between Sag Harbor and Greenport may also finally start soon, allowing day trips into the belly of the Hamptons beast—and an escape route at night.

What’s New

Biere, a pub that serves live music with its tapas and meatballs and Belgian craft beer, began service last fall. Vines & Branches, an olive-oil-and-balsamic-vinegar tasting room, opened on Main Street in March.

Rental Listings

A four-bedroom, two-bath shingled farmhouse (pictured above).
Cost: July: $8,000; August: $12,000; July–Labor Day: $17,000
Pluses: Close to the LIRR and Jitney.
Minuses: No central air.
Agent: Jerry Cibulski, Century 21 Albertson Realty (

A two-bedroom, one-and-a-half-bath apartment.
Cost: August–Labor Day: $4,000
Pluses: A huge living room, a backyard, and a beach at the end of the block.
Minuses: You don’t have the entire house, but there are separate entrances.
Agent: Jocelyn Meyer, the Corcoran Group; listing No. 75315.

A Perfect Day

Begin with a walk to Mitchell Park and its antique carousel. (There will likely be a show to catch at the amphitheater later in the day.) Score some retro finds at the Vintage Vault, which opened last year, then stop by the Greenport Harbor Brewing Company for a pint. Since you’re at the shore, down some clams at Noah’s. While away the afternoon with a North Fork winery tour or high tea at Greenport Tea Company, and end the day with snacks at the Frisky Oyster and dinner at the Greenporter Hotel’s Cuvee restaurant. The pomegranate martini comes highly recommended.