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Pricey Homes Almost Certainly Headed for the Scrap Heap

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"Tear downs" are not a new phenomenon, but dropping millions on a house just to knock it down is now becoming a proud tradition among America's rich. Billionaire hedge fund manager David Tepper—you know him as the guy who keeps $100M in a savings account—started a trend when he bought a 6,200-square-foot oceanfront house in the Hamptons for $43.5M then proceeded to knock it down and begin construction on a 15,000-square-foot replacement. On the West Coast, Paramount Pictures chief Brad Grey ruffled feathers when he bought Frank Sinatra's house, tried to flip it for $20M, and then tore the whole thing down just to relist it for the same price. Some high-end sellers have gotten wise to this tactic and have started to market their houses as the perfect place to, well, build a new house. This 3.7-acre waterfront estate in Greenwich, Conn. sits inside the guard-gated Mead Point Association and has a serviceable '70s house designed by notable local architect Peter Ogden. That's all well and good, but someone paying $8.75M for the site is going to have a hard time reconciling that price with the dated condition of the place. Break out the wrecking ball!

? For those interested in pulling a "Brad Grey," there's always this mediocre house on a prime lot overlooking the Bel-Air Country Club in L.A. If the facade elicits a resounding "meh," the price sure doesn't, at a hearty $7.995M. The brokerbabble doesn't even attempt to sell buyers on the existing structure, saying it is "sold 'as is' as a development opportunity" and including many references to huge nearby sales of late. The 0.75-acre site is the showpiece here, and never before has the word "charming" been used as more of a backhanded complement.

? Back in Connecticut, where these sorts of demolitions seem to be quite common, this waterview cottage has plenty of charm, but probably not enough space to save it from the wrecking ball. The 1,300-square-foot, three-bedroom house occupies a prime one-acre lot in Old Saybrook, Conn., about two hours drive from Manhattan. The broker has been sure to delineate the boundaries of the generous property in the listing photos, while alluding to the "unlimited possibilities to create your dream home." The price for the possibility of creating a dream home? $5.6M. At least that's cheaper than the $30M asking price on Katharine Hepburn's former estate around the corner.

? Unsightly historic homes of Northern California, you too are not free from the tear down scourge. This—again, "charming"—1934 "Carmel-style" home in Kentfield, Calif., north of San Fran, might be listed for $2.7M, but the brokerbabble sells the structure down the river, calling it "a major remodel or teardown" and declaring that the "value is in this estate lot in a neighborhood of significant homes." Curiously enough, there's no mention of the size of the lot, though it is vaguely described as a "huge rolling lawn that could easily be expanded."

? And now, for one of the saddest listings of all time, from a seller unwilling to admit their property is a tear down, but who must know it in their heart of hearts:

Formerly an award winner on the Street of Dreams, Cinque Terre by Carmen Domingues was once the shining star at the Home Parade!...Unfortunately for its owners, this dream was short lived, ending for the last four years in the most terrible nightmare and lawsuit. Today the once grand Cinque Terre is available for sale in an "AS IS" condition having again the potential to make the dream of a brave "fixer upper" come true. Although Cinque Terre Villa had suffered terrible vandalism, water damage and neglect, the home can be restored.The chances that someone will come along to tackle the restoration of someone else's decrepit former dream house are slim, but someone might pony up $1.2M for a sizable lot on a lake outside of Orlando, Fla. · Billionaire Forced To Pay $2.75 ATM Fee In East Hampton [Curbed Hamptons]
· This Is Where David Tepper's $43.5 Million House Used To Be [Curbed Hamptons]
· Brad Grey Razed Frank Sinatra's Holmby Hills House and is Still Asking $20 Million For the Land [Curbed LA]
· 505 Indian Field Rd [Zillow]
· Bel-Air Country Club [Sotheby's International Realty via Zillow]
· Fenwick Cottage [Sotheby's International Realty]
· Katharine Hepburn's Connecticut Paradise on Long Island Sound [Curbed National]
· Del Mesa Heritage Estate [Sotheby's International Realty via Zillow]
· 16635 Arezo Ct [Zillow]