No place else captures the bucolic yet bombastic duality of the Hamptons quite like Wainscott. This hamlet in the Town of East Hampton is where farm-centric past merges with trendy present, which might explain why the styles of homes here range from humble farmhouse retreats to some of the boldest designs on the East End. To Wainscott’s south and east, the Atlantic Ocean and prestigious Georgica Pond neighbor coveted waterfront real estate; the latter is where you'll spot some of the most eye-catching estates in the area. Beaches along the ocean are beautiful if unimaginatively named — Wainscott Beach, most obviously, and Town Line Beach, which falls on the border of East Hampton and Southampton, being the largest. Further north, the setting feels vastly more unclaimed. The residences in this rural and woodland environment almost hide among the trees, though sand and surf are never far.