The old adage that one can't lose money on Manhattan real estate doesn't seem to be holding up.

Recently released city records indicate that apartments in prime Manhattan neighborhoods are selling for less than their purchase prices — a phenomenon that until now was virtually unheard of in the seemingly invincible New York City real estate market.

Among the apartments selling for a loss is a unit at 80 John St., in the financial district, which recently sold for $590,000, much lower than the $720,000 selling price in January. At 515 West End Ave., on the Upper West Side, an apartment recently sold for $2.1 million — $50,000 less than its 2005 purchase price. There are also apartments currently on the market that are listed for below their previous purchase prices: A three-bedroom condominium at 166 Duane St. in TriBeCa — the wealthiest ZIP code in America, according to Forbes magazine — is on the market for $4.495 million, well below the $4.7 million paid for the unit in April.

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