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.

1-bedroom, 1-bath furnished condo in converted hotel, $279,000
Selling Points: In a 1928 Tudor-style manor, on 8 acres of land, with indoor and outdoor pools and tennis courts.
Agent: Pospisil Real Estate; 631-668-5200.

2-bedroom, 2-bath, seventies ranch on 1/3 acre, $659,000
Selling Points: Recently renovated kitchen. Houses nearby have sold for over a million.
Agent: Lynden Restrepo, Prudential Douglas Elliman, 631-668-6565.

5-bedroom, 4.5-bath shingled contemporary on 1 acre, $6.5 million
Selling Points: Stone fireplace, gym with steam shower, private dock, waterside pool, 1 acre of underwater land, 2-car garage.
Agent: John D’Agostino, Martha Greene Real Estate; 631-668-2811.

4-bedroom, 3.5-bath farmhouse (with 2 barns), on 17.8 acres, $17,000,000
Selling Points: New construction, operating as a cattle, sheep, and horse ranch. Borders thousands of acres of coastal preserve.
Agent: Lynden Restrepo, Prudential Douglas Elliman; 631-668-6565.