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Curbed Cup Round 1, Heat 3: Chilmark vs. Nantucket

The annual Curbed Cup kicks off over the bridge this week with eight enclaves vying for the very prestigious faux trophy and bragging rights as the Cape and Islands' Best Neighborhood of the Year. We're including towns and villages in our Cape Cod, Martha's Vineyard and Nantucket definition of a neighborhood, rounding up if you will. That said, we'll have one match-up per day, with polls staying open for 24 hours. Let the eliminations commence!

CrispinHaskins on Instagram/Nantucket blACKbook on Instagram

Curbed Cup 2015 voting continues today with an all-island showdown in which the Martha's Vineyard town of Chilmark faces off against the one and only Nantucket.

As home to the summer White House, the Martha's Vineyard town of Chilmark probably has the ultimate in bragging rights, at least for now. In fact, a former Obama rental is on the market for a whopping $19.1M. In addition, the tony town had some other rather stunning real estate list this year, although good looks and iconic architecture weren't enough to keep the pricechopper away.

Ferrying over the Nantucket where pricey real estate continues to dominate with the majority of the Cape & Islands most expensive listings. Case in point, the June sale of a $26.5M Brant Point estate. Of course, the the Grey Lady has its share of iconic, unique, loft-like, and little listings as well. In addition, the island could be getting its first-ever apartment complex any day now.
So Curbed readers, which town should advance? Submit your vote for the locale you think deserves to move on to the next round, toward 'hood of the year bragging rights and the faux trophy.
Poll results