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Curbed Cup 1st Round: (2) Southampton vs. (6) Montauk

The Curbed Cup, our annual award to the Hamptons neighborhood of the year, is kicking off with 8 towns/villages/hamlets vying for the prestigious fake trophy. This week we'll have one matchup 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.

In this corner is elegant, gracious, beautiful Southampton. This year the town saw some big sales, including Wooldon Manor on Gin Lane, which sold for the second time in eight months for about $80M. EDM mogul Robert F.X. Sillerman sold on Meadow Lane for $37M, and the "Something's Gotta Give" house, also on Meadow Lane, sold for $41M. There was a controversy over the replacement for historic house A-Weel-Y-Mor at 40 Meadow Lane. Neighbors said the modern house would be too large and out of scale with its historic neighbors. There was a kerfuffle over a proposed senior housing development as well. Gardenside, the former home of Consuelo, Duchess of Marlborough, was put up for sale for $28M. On the lower end, good old Toile House made its triumphant return to the real estate market.

Doing their best to tarnish the sterling reputation of Southampton were the Kardashians, who swarmed around the town filming their reality show all summer and opened a shop, Dash, in the village. Let's pretend that never happened. A classier happening was that the legacy of former slave and resident Pyrrus Concer was celebrated with the return of the Agawam Ferry.

Hoping for a repeat of its 2013 Curbed Cup victory is Montauk. The big news in the town was the debate over how to shore up the downtown beaches, and the answer is apparently sand tubes, but the work may not be completed by Memorial Day. The town was represented on the small screen with the Showtime series The Affair, and supermodel Gisele shot a Chanel Number 5 ad there too. The Montauk Movie shut. Real estate was fairly quiet, but as usual, the restaurant scene was active. Jennifer Oz Leroy and Seth Levine took over the new Gurney's Seawater Grill, then left. The Harbor Bar & Grill opened, and Duryea's was sold, but will continue to operate next summer. The other big story in the town was the plans for redevelopment of the East Deck motel, which sold last year. It may be purchased by East Hampton using CPF funds.

Poll results