Greenport

An excellent base camp for exploring the North Fork
After the stretch of smaller and more bucolic communities between Riverhead and Southhold, the village of Greenport can feel like a welcome oasis of choices: shops, eateries, sidewalks to stroll, and activities located all in one place. Greenport has a vibrant food scene, and the most interesting choice of accommodations of any North Fork town.

Mitchell Park features waterfront paths and docks with views stretching to nearby Shelter Island, which sits just a short ferry ride away. The Long Island Railroad makes its last North Fork stop here, too, and the marina regularly has tall ships, charter boats and yachts pulling into port, as well as recreational boaters. There’s also a swimming beach right in town.

Modest cottages, historic homes, renovators’ dreams
Greenport’s housing stock often changes from block to block. The drive in and out of town on Route 25 passes two rows of striking 1800s Victorians. To the immediate west and north of the town center, the village has smaller wood-frame homes and cottages that sit shoulder-to-shoulder with one another. Drive north toward Long Island Sound, and the homes have larger lots and come in a mix of styles: farmhouses, Colonials, the rare contemporary. There’s a high-end market here, but bargains, too. You can still find a waterfront fixer-upper for around $1 million if you look hard enough, and a 2- or 3-bedroom weekender can be had for between $500K and $700K.