Like Brooklyn, Montauk has long been defined by an anti-scene. On the surface, it’s a blue-collar holdout, with an abundance of inexpensive roadside motels, dive bars with sharks’ jaws on the walls, and an annual hot-dog-eating contest. Nightlife revolves around the boozy Friday-night karaoke competition at Liar’s Saloon, where the local fishermen always win.

Recently, perhaps inevitably, the town’s low-key charm has been attracting well-heeled folks who could afford to live pretty much anywhere and previously tended toward the Hamptons. In January, J.Crew CEO Mickey Drexler paid a record $27 million for Andy Warhol’s old Moorlands estate, which had sat on the market for years. Now for sale nearby is an oceanfront five-bedroom—asking price, $24.95 million—not far from the cliffside spreads occupied by the likes of Nets owner Bruce Ratner and Montauk pioneer Paul Simon.

Upper-middle-class New Yorkers—people who have a two-bedroom in Manhattan or a decent house in Brooklyn, rather than a limestone on East 64th—are also buying weekend homes in Montauk because parcels are smaller and prices are lower than farther west. In Hither Hills, for example, an ocean-view property can sell for $1.2 million to $2 million if it’s on less than an acre. “You don’t typically find these types of dense seaside communities on the ocean elsewhere in the East End,” said John D’Agostino, a broker at Martha Greene Real Estate.

But everything, from Moorlands to the bargain areas, is showing signs of price creep. In Culloden Shores—where two-bedroom “Leisurama” homes sold by Macy’s for under $20,000 in the sixties now go for up to $700,000—a nearby one-plus acre, bluff-front parcel sold for an area high of $1.85 million (more than four times the price of a similar plot in 1998). As in Brooklyn, affordability can cost a fortune.