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Good taste: hard to replicate but can be bought; house is a shambles, price is $25 million; any way you want it: real estate with instant gratification; when even a small pond looks golden

Pedigree on the Pond

One problem with old money is that it’s gotten so expensive. At least the old money look in real estate. Take a great old house, say with painted floors and painted furniture, modest bathrooms, and a disdain for household fads. Put it in the right estate area location, and it’s irreplaceable. Market amenities can be replicated; this kind of assured good taste can’t be. But, this being the Hamptons, at a high enough price it can be bought.

Architecture: Attributed to Stanford White, but no hard documentation. In any case, it is classic, restrained but also a bit surprising. The main room is three stories high with an enormous north light window. Details such as period wainscoting and a paneled library are extraordinarily refined.

Site: Nearly two acres on an inlet of Georgica Pond, with views as well as that palpable, well-heeled serenity that big money perfects.

The inside word: The location and prestige should appeal to the investment banker crowd, but the old money taste and lack of voguish amenities will require a more unusual and discriminating buyer. We trust whoever pays the $12.5 million will appreciate what an understated masterwork this place is.

Shabby Chic

If old money is expensive, decrepit money is even more so. We recently visited Maycroft, an extraordinary nineteenth century estate in North Haven. Built in 1885 as the home of the oh-so-rich Aldrich family, it operated from 1917 to the mid 1990s as a boarding school run by the Episcopal Church. The main house is a shambles but the property remains gilt edged.

Architecture: It was at one time an interesting combination of cottage styles, but it doesn’t matter anymore. The main house is too far gone for conventional restoration and the second house is not important enough.

Site: Absolutely stunning. It is staggering to think a 43-acre estate with 1,000 feet of waterfront on Sag Harbor Cove is on the market.

The inside word: Remarkable as it is, this property is not an easy sell. The price of $25 million is only a start. For anyone keeping it as a private estate demolition and then construction costs must be added. For someone who wants to subdivide the property—the most likely use, as we see it—it will be a long, hard process with lots of community opposition. But the results could be sublime.

Natty and Nice

Almost across the street from Maycroft we found an estate that is nearly its polar opposite. Generations younger, spiffy and in tip-top shape. More Ms. Hilton than Miss Haversham, the place is polished and unblemished. It appeals to the buyer who wants it all—right now.

Architecture: A Hamptons style of traditional materials used in a contemporary way, with lots of glass and light, and a clean, unfettered sensibility. Built in 1980 before style veered toward period reproductions with a Ralph Lauren sensibility, the house is quite sophisticated in its way.

Site: 3.7 acres with 260 feet of waterfront on North Haven a bit north of the Sag Harbor bridge. The acres of lawn include a separate building lot.

The inside word: Depending on how many millions you want to shell out, choices are available. House, pool, poolhouse and stainless outdoor kitchen on 1.5 acres are offered for $5.5 million. The extra 2.2 acres of lawn is $3.5 million. Both pieces are waterfront, and the package is $9 million. Instant gratification is built into the price.

Make a Splash

Wraparound porches are old news—though after all these years they are hard to improve on. We’ve seen wraparound kitchens and fireplaces and windows mentioned in real estate ads, but when a house description with a wraparound pond recently crossed our desk, it really caught our attention.

Architecture: The brokers call it a farmhouse, but they obviously don’t mean the old family farm. At 6,500 square feet it might remind you more of Marie Antoinette’s dairy at Rambouillet.

Site: Fourteen acres in Bridgehampton, with a pond that—what can we say? —wraps around the house. Guest house, small dock and a fortune in landscaping.

The inside word: Waterfront on big ponds was always more expensive than waterfront on small ponds. But when the pond is private and as intimately close to the house as a moat, size is less important. Also as demand increases and available waterfront doesn’t, every pond begins to look looks golden and prices of pondfront dazzle. Offered at $21 million.

Vermont barn settled in Sagaponack dunes; is that a tennis court or your front yard? all wet: submerged underwater acreage; don’t laugh, that’s really the price

Making sense of the very confused maze of ownership of the Hamptons real estate brokerages and the big money behind them. Warning: leave your logic at the door.