For purists who miss the good old days when the Hamptons were quaintly, adorably agricultural, there’s the low-key neighbor, Shelter Island (the ferry pushes off from North Haven and Greenport, Long Island). This lavish, airy four-bedroom mansion is in the upper range, but you get bamboo floors, cathedral ceilings, and views of Gardiner’s Bay; there’s even a heated outdoor pool overlooking the water. It’s all in keeping with the island’s “beachy but elegant” vibe, which mixes fried-clams-on-paper-plates dining at Two Eds with invitation-only golfing at Gardiner’s Bay Country Club.
Cornwall, Litchfield County
Perfect for urbanites wanting to play country squire, this is at the high end even for Litchfield County, with far more space and amenities than the norm. The 92-acre property consists of a 3,600-square-foot main house, a two-bedroom guest house (for your staff, perhaps), a gunite pool, a pond—and, for equestrians, 40 acres of pasture. For privacy freaks, the driveway alone is nearly half a mile long, and there’s even beach access to nearby Lake Waramaug. If you do leave the grounds, you can attend the Litchfield Jazz Festival or stock up on treats at Belgique Patisserie & Chocolatier.
Remsenburg, the “pre-Hamptons”
Technically, this clubby little hamlet, ten miles west of the Shinnecock Canal, isn’t even in the Hamptons, but that’s why you get double the value; a fully tricked-out house like this would cost $100,000 farther east. There are five bedrooms, four baths, two fireplaces, a boat dock with floaters for kayaks, an outdoor Jacuzzi, a heated gunite pool with waterfall, and a tennis court. No trendy restaurants, no gourmet food shops with attitude—not even a town, per se, except for a post office. But you save as much as an hour on the commute, because it avoids the bottleneck on Route 27.
Willow Street, Southampton Village
The meticulously renovated house and cottage with a total of three bedrooms have everything their real-estate broker-owner has ever been asked for by renters. In particular, multiple entertaining areas—a breakfast patio, a gazebo next to the gunite pool, a covered porch for afternoon tea, and a pergola with a blue-stone patio for barbecues at sundown (such amenities justify the slightly higher-than-average price). Don’t expect to join the Southampton Association—the house is a little too hard by the railroad tracks for that. But it’s got that Southampton Village feel.