Vacation Homes Listings

Sag Harbor

Once known as the “un-Hampton,” this former whaling port now boasts the kind of upscale amenities that have long characterized the rest of the South Fork. Yet some of that “olde time charm” remains in the shops, homes and byways that dot this scenic village.

Sag Harbor’s centuries-old streets are lined with grand houses, some of which hark back to whaling days. These historic houses sit cheek and jowl with restaurants and shops where you just might get a peek at literary or Hollywood celebrities browsing through store racks or dining at the next table. Local sites include Canio’s Books, which features author readings; the classy American Hotel, and, at the north end of Main Street, a small windmill which houses the Sag Harbor Chamber of Commerce.

Close your eyes, smell the salt air, and you can all but imagine the hustle and flow of whaling days when Sag Harbor’s streets were a cacophony of foreign accents and its connections to commerce spread around the world.


Sag Harbor’s streets slope down to the bay like rivers running to the sea. If you stand at the end of Long Wharf, the harbor is a picture postcard of pleasure boats that come from far and wide to moor in Sag Harbor. And while whale oil and lumber no longer move in and out of Sag Harbor, you can imagine the tall ships sidling up to the Long Wharf.

The village offers all manner of dining and refreshment, and a short bike or car ride brings you to a glorious sunset over Noyac Bay or a cooling plunge into the Atlantic Ocean. At the windmill/visitor’s center, in addition to some friendly help, you can pick up a map showing where to find the local architectural and historical treasures, museums, shops and eateries.

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