Curbed Cup 1st Round: Westhampton/WHB (8) vs. Sagaponack (9)

First up, Westhampton/Westhampton Beach. A reader enthused, “It has the vibe of Montauk without the riff raff, a quaint main street without a bazillion Ralph Lauren stores, new refurbished supermarket (Best Market), and we’re awaiting the final product from Discovery Land Group’s development of the Dune Deck. Its proximity to Manhattan is extremely appealing. And let’s face it: tell me the difference between Rogers Beach and Coopers Beach. Also a great golf course/country club and plenty of access for tennis. It lacks a decent restaurant scene so if you don’t get enough of that in Manhattan you are only 20 minutes away from Southampton and there are also a couple of good choices in nearby Quogue.It does have the Patio and Pizzetteria Brunetti is outstanding. Best kept not so secret is Johnny Scotts Surf Shack. What a night out at the beach should be all about.”

By Americasroof - Own work, CC BY-SA 3.0

Sagaponack, once again the nation's priciest zip code, is often in the news despite its diminutive size. A 32-acre parcel north of the highway came onto the market, asking a whopping $65M. Lloyd Blankfein of Goldman Sachs finally unloaded his Sagaponack property after a mere nine years on the market; Ashley Olsen toured homes in the area but didn’t buy (that we know of, anyway). Infamous New York landlord Steven Croman and wife Harriet made the news again; they’ve been building a new oceanfront house in Sagaponack. Can this small but mighty village win its first-ever Cup?