Life Out East

What Does 'South of the Highway' Mean?

One term you’ll hear constantly in discussions of Hamptons real estate is “South of the Highway.” It’s such a common phrase that we even have a search filter for it on Out East — so you can look exclusively for homes that have been deemed south of the highway. But while the designation “South of the Highway” seems like it should be clear, it can get pretty tricky in some places. Here, we’ll explain what the term really means, and why people value what it confers.

What Does ‘South of the Highway’ Mean in the Hamptons?

In the Hamptons, the “highway,” as most people know it, is the Montauk Highway — the main road running from west to east through the Hamptons. This road wears a number of numerical designations, but is best known as state Route 27. So, on its face, the term “South of the Highway” would seem to mean anything in the Hamptons south of Route 27, from Shinnecock Hills, to Wainscott, to Beach Hampton. And in many places, that’s correct. But not everywhere.

Where Is ‘South of the Highway’ Not Just South of the Highway?

In Southampton Village, things get tricky. Here, there are two highways. There’s the newer, larger one — Route 27 — and the smaller Old Montauk Highway, which now consists of several named streets in Southampton Village. From west to east, those streets are: Hill Street, Jobs Lane, Main Street, and Hampton Road, the latter of which rejoins with the newer Route 27 east of town at Flying Point Road.

For this portion of Southampton, “South of the Highway” does not mean anything south of Route 27, as it would include the whole of Southampton Village. Rather, the term applies to anything south of Hill Street, Jobs Lane, and Hampton Road — i.e., south of the Old Montauk Highway. That’s a much smaller and more exclusive slice of land.

What Is Desirable About Being South of the Highway?

As with many things in the Hamptons, the designation “South of the Highway” is about prestige — people consider there to be more of it when a home is farther south, away from the regional thoroughfare. But there are practical reasons behind this desirability, too. In Southampton, especially, homes south of Hill Street and Hampton Road are much closer to the ocean than those homes merely south of Route 27. Many, in fact, are walking distance from the water. And of course many of the village’s toniest streets — such as Meadow Lane and Halsey Neck Road, with their hedgerow-hidden mansions and hundreds of feet of beachfront — lie south of Hill Street. So along with being a handy label, “South of the Highway” implies being somewhere particularly nice.

It’s not just in Southampton where being south of the highway matters, either. The most upscale hamlets and villages in the Hamptons, like Sagaponack and East Hampton, all tend to lie south of the highway. (And the fanciest parts of villages that span both sides of the highway are generally south of it.) So in the Hamptons, being “South of the Highway” means having the most elite real estate in a region full of it — and enjoying all the prestige that comes along with it.

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