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Curbed Cup 1st Round: Southampton (6) vs. Sagaponack (11)

The Curbed Cup, our annual award to the Hamptons neighborhood of the year, is kicking off with 16 towns/villages/hamlets vying for the prestigious fake trophy. This week we'll have two matchups per day, and all the results and the full tourney bracket will be reviewed on Friday. Voting for each pairing ends 24 hours after it begins. Please remember—no wagering.

The Curbed Cup kicks off this week. Let's give a warm Curbed welcome to Southampton (6) and Sagaponack (11)!

Perennial also-ran Southampton still boasts some of the Hamptons' priciest real estate. Just recently it made headlines when a Meadow Lane estate became available for summer rent for $2.5M. A new development of ultra luxury homes is being built on Old Town Lane; the first is asking $45M. One historic estate, the Bouwerie, was recent razed; another, Four Fountains, is now on the market for $35M. Don't want to own something big? New high-end boutique hotel rooms are being proposed adjacent to the Southampton Inn, while Chris Burch's tiny Cocoon9 houses were shown off over the summer.

Sagaponack, this year the nation's second priciest zip code (curse you, Atherton, California!), is often in the news despite its diminutive size. David Tepper's spite house on the ocean was finally completed, and Marc Goldman's attempts to build on his land ended up in his planting a Christmas tree farm there instead. Party animal Marc Leder enjoyed his first summer in the hamlet. Several of the Houses at Sagaponac, the ill-fated modern development, came on to the market, but are lingering because of proximity to the airport (we surmise). Can this small but mighty village win its first-ever Cup?

Poll results