bestcoastalhomes.comWaterfront and luxury real estateLife’s a Beach: Orient

Located on the North Fork at the tip of Long Island, Orient is a hidden gem.

Off the beaten path and quaint as heck, the tiny waterfront hamlet is one of the true rarities on New York’s popular East End. It’s a place teeming with charm that has been nonetheless improved by and yet left mostly intact from big Manhattan money.

Originally settled by only a handful of families that had been given a land grant by the King of England way back in the 17th Century (the Kings, the Terrys, the Glovers, the Lathams, the Tuthills and the Vails), the 5-square-mile spit of land in the Town of Southold sits on the easternmost parcel on the North Fork. Fun fact: During the American Revolution, it was used as an operation base for British commanders, including the infamous Benedict Arnold, whose headquarters was a local tavern on Village Lane, which today serves as Orient’s main street.

Walking along the peaceful and shady sidewalks and streets, lined by Victorians, shingle-style and New England-type clapboard homes, it’s easy to think of this as a place that has been thankfully lost to many modern “improvements.” The air is filled with birdsong, and nearly every single residence boasts an American flag, a throwback actual wooden screen door, or both. And even though, like it’s larger but similar sister of Sag Harbor on the South Fork, there is a fair share of millionaires and fancy boats (literally docked on the waterfront that comes up behind Village Lane), but it’s generally privet without the pretense.