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Curbed Cup 2nd Round: (6) Bridgehampton vs. (7) Montauk

The Curbed Cup, our annual award to the Hamptons neighborhood of the year, is moving on to the second round. This week we'll have two matchups, and all the results and the full tourney bracket will be reviewed on Friday. Voting for each pairing ends in the wee hours the next morning. Let the eliminations commence!

For many people, Bridgehampton real estate means the Sandcastle. And why shouldn't it? Any home renting for $250,000 a week is going to turn heads! Of course, there are other notable homes in town, including developer David Wine's award-winning beach house and the Windmill house where the Clintons stayed. Since all these boldface names need to eat, Bridgehampton also saw a sort of steady dining scene, with new additions like the Southfork Kitchen, and some losses, like Almond. But the "number one reason to vote Bridgehampton?" According to one commenter, it's the 30-year-old "softball game at school st every sunday morning during the summer."

In terms of development action alone, Montauk's definitely on top. In the past year, more monumental Montauk real estate hit the market than anyone would've liked to see. The East Deck Motel, Salivar's, the Montauket Hotel, the Inlet Marina, and even a portion of the Deep Hollow Ranch (you know, the one J.Crew CEO Mickey Drexel just purchased), are all up for grabs! And with new additions like Navy Beach and Edition, The End's dining and shopping scene doesn't seem to be letting up either. Add to that America's most controversial 7-Eleven for proof that everything is happening in "the only town remaining with organic Hamptons charm."

Poll results

[Bridgehampton photo via; Amagansett photo via; Montauk photo via]