Southampton

Traditional shingle style dominates here in the land of laid-back luxury. Shaped by the American aristocracy of the early 20th century, Southampton’s classic elegance draws second-homeowners and weekenders who seek to spend their summers flocking to Coopers Beach. Adding to the town’s appeal are its sidewalk cafes and exclusive Main Street and Jobs Lane shops, including Hildreth’s, the oldest department store in America. History and commerce coexist peacefully, as successive generations of families—from the earliest farmers and landowners to society types and captains of industry—have made their homes in New York’s oldest village, which was founded in 1640 and named after the Earl of Southampton. Pristine privet hedgerows protect commanding homes with sweeping ocean views in the estate section. There are a number of prestigious addresses, but none more so than Meadow Lane, often referred to as “Billionaire Lane,” and Gin Lane, which represent two of the most exclusive streets in the nation.

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