Greenport is a maritime village with a working harbor, an antique carousel, and some of the East Coast's most celebrated vineyards just outside its edges. The village is bikable from the house — grab a cruiser, coast into town for coffee and oysters, and be back before the pool warms up.
Wood-fired pizza, local oysters, and seafood under a century-old oak right on the beach
Waterfront spot for locally sourced seafood caught by line, trap, spear, or hand
Village standby for seasonal comfort food, seafood, and a proper cocktail
Beachy Southold spot for seafood, cocktails, and sunset views
Wood-fired coastal cooking on 8 Hands Farm in a relaxed Greenport setting
Shuck-your-own at the dock — pair with a cold bottle
Working fish market and seafood counter — lobster rolls, fried clams, and local catch
Long-running fish market and kitchen for fresh seafood and lobster rolls
Oversized doughnuts and coffee on Love Lane
Dockside bites and cocktails on Peconic Bay at The Shoals in Southold
Globally inspired coastal bites and craft beverages at Orient Beach State Park
Private Neighborhood Beach
Keyed access, a short walk from the house
Antique carousel, harbor walk, and the heart of Greenport Village
Calm bay beach, maritime forest, picnic grounds, and easy shoreline exploring
67 Steps Beach
67 steps down the bluff to a rocky Sound beach with spectacular sunsets
Woodland and bluff trails down to an undeveloped Sound beach
Easy wooded trails past Inlet Pond and bird habitat to the Long Island Sound
Quiet 1.3-mile trail network through woods, wetlands, and open fields
Short hike to a quiet beach where the inlet meets the Sound
Ten minutes to a slower world — bring the bikes
Regenerative farm with pasture-raised meats, eggs, a butcher shop, and farm store
Biodynamic Southold farm stand for just-picked vegetables, flowers, and local goods
Certified-organic produce, specialty vegetables, and farm-kitchen provisions
Certified-organic, pasture-raised chicken and eggs from a family farm
Summer stays include a Deep Dive Farm CSA share — pick up Saturday morning at the Greenport Farmers Market
Organic, biodiverse farm stand with heritage produce in Orient Point
Beautiful tasting room nestled among lush gardens — our pick for an unhurried afternoon
40-acre farm brewery with sprawling outdoor seating, food trucks, and weekend music
Original Greenport tasting room in a renovated 1860s firehouse
Bluff-top tastings overlooking the Sound
Family-run vineyard known for regenerative farming and expressive North Fork wines
Rosé-focused vineyard with a transportive French-country garden