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Not The Hamptons: Southold

This is a place for people who’d rather avoid the scene of Hamptons-land. It’s full of relaxed charm—“People love the history here,” says Corcoran broker Sheri Winter Clarry—and the Peconic Land Trust means it’s surrounded by nature preserves and a system of hiking trails. Halstead Property’s Cornelia Dodge knows a number of Hamptonites who’ve decamped to Southold: “Because of Long Island Sound and the Peconic Bay, it’s got lots of wildlife and places to explore.” It’s also a good place to search for a rental, simply because it has so many: According to, Southold has more North Fork listings available than anywhere right now, suggesting that it’s a moment to make an offer and catch a bargain.

What’s New

The long-fallow Mill Creek Inn & Marina is being renovated right now and is poised for a rebirth as an 8,989-square-foot restaurant with boat slips and a dock.

Rental Listings

A three-bedroom, one-bath cottage.

Cost: July: $8,000; August–Labor Day: $8,000

Pluses: Fifty feet of frontage on Long Island Sound, plus a studio with easel and drafting table.

Minuses: It’s on the small side for a three-bedroom.

Agent: Sheri Winter Clarry, the Corcoran Group; listing No. 71863.

A Perfect Day

Start with a breakfast of organic produce from KK’s the Farm on Main Road. Wait an hour, then suit up for a run to Horton Point Lighthouse, where there’s a little maritime exhibit. Walk down the “hundred steps,” then run back to town and grab a crab-cake sandwich from Erik’s. (If you’re not a runner, spend the morning at Founders Landing beach; it has a playground for kids.) Then head to the Port of Egypt to rent a boat for the afternoon. Dinner’s at the North Fork Table & Inn, whose executive chef, Gerry Hayden, was just nominated for a James Beard Award.