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The art of being very rich and seemingly rural; spec house OK but not unrivaled; simple pleasures with a hefty price tag; a splendid shingle style roof over some well-coiffed heads

Wainscott Gentry

Wainscott occupies a special place in the social geography of the Hamptons. With the Wainscott Association (or the Settlement, as old-timers refer to it) setting the tone, the hamlet, or at least its estate area, manages to be very rich and seemingly rural. Houses, as a result, are uncomplicated but expensive.

Architecture: Simple unassuming forms, sea-bleached shingles and restrained detailing manifest its Wainscott origins.

Site: On 1.2 acres with an adjacent one-acre building lot. The separate building lot adds value—but separating the two is unthinkable. It would destroy the privacy and bucolic qualities.

Condition: Fully renovated four-bedroom cape, decorated by Vicent Wolfe, soon to be in Elle Décor. We may safely assume there is nothing out of shape here.

The inside word: This is a dream location—with views to the south over the fields of the Babinski farm and to the west the Osborne strawberry patch. Este Lauder lives across Wainscott Main Street and the Wainscott landed gentry reside to the east in the Association. Definitely a rare offering—and definitely reflected in the price of $5,300,000.

Fast Forward Home

Had enough of austerity? Need instant gratification? A nice summer pick-me-up? Here is a brand new estate ready to go. All you have to do is get over this repetitive seasonal feeling that you’re not as rich as you used to be and write the check for $4,575,000.

Architecture: Gabled dormers, a turret entry, and the repetition of geometric forms set up a pleasant rhythm that is reinforced by the architect’s disinclination toward exterior embellishment. Nice interior touches like coffered ceilings and raised paneling.

Condition: Ready to go. Just bring checkbook, bathing suit and tennis racquet.

Site: Landscaped and gated two acres in Bridgehampton south, adjacent to working horse farm.

The inside word: It’s a spec house, and certainly not unrivaled. But perhaps because a European team of developers planned it, it’s not run of the mill either. There’s some drama where you want it but nothing that jars the eye or the mood. And there’s plenty of luxury, including five bedroom suites with marble baths, where you need it.

Horse Country Harmony

Can you still get privacy—real privacy—in the Hamptons? Not the kind fabricated by fences and landscaping, but created by the land and sea and sky, close to nature and far from neighbors? With air and light and views? It’s difficult and it’s expensive—but the answer is yes.

Architecture: Authentic barn—a main house and a 200-year-old Vermont barn converted to a guesthouse. Given the rural setting in Bridgehampton horse country, the simple architectural style in on target.

Condition: Basic, unadorned, well maintained main house with three bedrooms; complete guest house with two bedrooms, as well as its own living room, kitchen and fireplaces.

Site: On a secluded lane off Scuttle Hole Road, this 10.6 acre property with splendid views of farmland and the ocean beyond gives you a classic painterly perspective of foreground, middle ground and horizon. Utterly simple and thoroughly satisfying.

The inside word: The two houses, large lot and long views all work together. There’s a lovely harmony, true compatibility, among the elements. We like country houses that don’t pretend to be anything else, and this place has integrity. Such simple pleasures, inexpensive elsewhere, carry a hefty price tag in the Hamptons: $4,900,000.

Splendor in the Grass

One thing about Southampton: we make every effort to see that no billionaire goes without shelter. The absorption rate here for the moneyed classes is prodigious, and while it may not rank among the country’s top ten social services, it nonetheless provides the privileged some wholesome activities between the Aspen and Palm Beach seasons. Here’s our choice for putting a splendid shingle roof over some well coiffed heads.

Architecture: It successfully meets a difficult and exacting standard: the essence of conventional shingle style. Not a riff on tradition and not an impersonation, but undiluted and real. It employs the best of inherited architectural forms without theme-parking or haphazard borrowing.

Condition: New and exceedingly well constructed.

Site: Three acres on Great Plains Road is certainly valuable and sought after, but another three would give this house the approach it should have. Pool, tennis, terraces, pergola and ambitious landscaping zoom in on estate character.

The inside word: Until recently a price of $11,500,000 would take our breath away, but now we look and simply ask: is the value there? Considering the size of the public spaces—plus the ten bedrooms and poolhouse—the endless amenities, and the unstinting quality throughout, we think some adroit buyer will be writing an awfully big check but unquestionably getting her money’s worth.

Saved by the house movers; serene if not quite authentically Asian; panoramic views from a Montauk hilltop; and an intact Greek revival wears its history well

The Guv’s house, and it’s not a mansion; an athletic complex; the best of three and a half centuries; and the Hamptons channeling rural England