Figuring out how much a home is worth in a vacation destination is often an uphill battle.

Whereas normal property markets have prices that are tied closely to square footage, size of a lot, quality of a building, and its proximity to basic services, many of those calculations go out the window when it comes to a market comprised of second homes. “Nobody needs anything out here,” says Chris Foglia, a broker at the Hamptons-based Daniel Gale Sotheby’s International Realty. “They all want.”

This is particularly true for the many vacation spots scattered across coastal Long Island. Southampton, Bridgehampton, Sag Harbor, Shelter Island, Westhampton Beach, and Hampton Bays are just a few of the more popular destinations for New York City’s upper class.

The very top of that class might not mind a market based on whims, but for the army of affluent professionals on a relative budget—the doctors, lawyers, and other mere millionaires—how far their dollars go, and where they go furthest, actually matters.

So, how to determine value in a market that defies logic? The answer might lie in a combination of hard data and anecdotal answers.

The Methodology
We asked Zillow, the online real estate database company, to compile the most recent 12 months of data on median price price per square foot in the aforementioned six major Long Island vacation destinations. (There are many more, obviously, though Zillow data are spottier in towns such as the villages in East Hampton, or further hot spots such as Fire Island and Bellport, so they aren’t included.) Then brokers familiar with each area weighed in.

The one constant? All the brokers said that this exercise was pointless. “I have customers who try to compare and contrast [properties] all the time,” says Seth Madore, a broker for Corcoran based on Shelter Island. “It’s just so different out here. Each property is, in essence, unique.”

Mala Sanders, a Corcoran broker who’s based in Sag Harbor, echoes that point. “We’re not dealing with blocks of buildings where the only differential is if an apartment has a view,” she says. “Out here, one house next to another can be vastly different in terms of the quality of the land and landscape.”

The Market
And that’s true. There are (comparatively) low-end condominiums in Southampton that are less than a five-minute drive from some of the most expensive mansions in the state. Even from block to block the houses, lots, and quality of construction change dramatically. Compiling data, then averaging out ZIP codes, is by definition painting a market with an absurdly broad brush.

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