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Built by a (very tasteful) rebel; maybe passé but on the right bay; part real (estate) and part fantasy; the power of context along with weathered shingles

Rebel Estate

We never knew Augusta Maynard but we wish we did. In 1980—when real estate prices were not quite as fizzy as they are today, but when the estate areas were even more definitively the place to be—she took an absolutely top notch piece of property on Great Plains Road, just a block from the beach, hired the modernist architect Ben Baldwin, and built herself a very refined two bedroom house. It was probably a mildly rebellious statement then. It seems absolutely radical now.

Architecture: A clean-lined cubist composition, spare and quadratic. While the design is very much suggestive of its time, age has been kind, and the house is as pleasing to a viewer today as it must have been to the owner and architect two decades ago.

Site: Blue chip Southampton estate area location. The lack of ornament in the house design is balanced by the lushness of 3.3 acres of rare and beautiful landscaping with pool and a substantial poolhouse.

The inside word: Every house has a destiny, and given the location this small gem is likely to be replaced by something in the grand palazzo style now in vogue. The gardens should certainly survive the bulldozer, so something of the Maynard style and taste will continue, as will the appealing legend of this property. Offered at $4.950 million.

Clam A Lot

Mecox Bay hosts a highly productive oyster population, a prolific community of soft shell clams, and a highly accomplished group of homeowners. While the shellfish are content to live communally and procreate in the muddy bottomland, the residents along the shoreline are determined to produce ever larger, more luxurious private habitats. So far, we have avoided an ecological showdown.

Architecture: You could see it as a simple waterfront retreat, the kind of place from which you’d go clamming—except today’s prices preclude that sort of thinking. What was a perfectly fine looking house several years ago just does not cut it in the age of cyclopean castles.

Site: Superb 2.25 acre waterfront lot with 500 feet of bulkhead, manicured lawns and panoramic views.

The inside word: A little boxy, a little passé, this house is not going to fulfill the needs of a typical buyer in this location. Especially one paying $6.5 million. But the site, nearly irreplaceable in the current market, can accommodate a 10,000 square foot house along with pool and tennis court. Perhaps enough to justify dishing out those millions.

Addams Family House?

The Byram house is one of those places in Sag Harbor that you have to notice, and for years we would smile a bit as we drove by. It is a residence to be sure, but at moments it appears to be a stage set, or a folly, or a dollhouse on hormones, or a Halloween decoration placed near the cemetery. It is a kaleidoscope of a house, at least in the mind’s eye, part real (estate) but also part imagination and fantasy.

Architecture: Italianate elements, normally expected on a large mid-nineteenth century home, appear here on a medium sized house. Ephraim Byram, a distinguished clockmaker, built the home in 1850, and perhaps that mentality was behind this unusual design.

Site: Located on Jermain Street, a busy but prestigious road, with quiet neighbors to the east—a cemetery. Brick terraces, gazebos, fruit trees, ponds and a fair amount of whimsy fill out the one-acre property.

The inside word: The tower fascinates. An observatory? A clock tower? Did Mr. Byram ever place a clock there? It lends a high fantasy touch and establishes the mood of eclecticism. With four bedrooms and five baths the house is not a joke and could be a fine family house, and we don’t mean just the Addams family. The price of $2.2 million also anchors the place to reality.

Longing and Belonging

From the late nineteenth century until WWII large shingle-style houses defined the general look of the estate areas in East Hampton and Southampton. Now, houses derivative of that style are built not just in these village areas, but also in the woods, in former farm fields and along the sandy shores of bays, ponds and inlets. Does context matter? Or is it just what we become accustomed to?

Architecture: Long porches, attic windows including diamond panes and an eyebrow shape, transoms and overhung gables recall older houses in the neighborhood. There is a pleasing rhythm and more symmetry than one would find in those older houses. The restraint is preferable to the overload we sometimes see.

Site: A bit more than an acre on Apaquogue Road, close to Georgica Beach in East Hampton—a place where money and tradition rule.

The inside word: Although a spec house, attention to detail in planning and building this six-bedroom house should give a well heeled buyer with $7.250 million just about everything he or she could long for: space, amenities and location. And once those shingles weather, that ineffable quality—context.

Quite possibly the most private location in the Hamptons; amenities piled on thickly; a bit of Fairfield County in the Bridgehampton hills

Elevator going up, price going down; no grand gestures but resolute confidence; formality with a light touch of romanticism; so-so house can easily be replicated but the views can’t