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Hamptons.com
April 30, 2015

The Dirty Little Secret Of Hamptons Real Estate

475
VIEWS
Sponsored Guest Post by Gary R. DePersiaby Sponsored Guest Post by Gary R. DePersia
in Real Estate
Home Real Estate

For years, prices of properties South of the Highway (SOH) have dominated the Hamptons real estate market. But, you might be shocked to find out that a trend is emerging North of the Highway (NOH).

The Times, They Are A-Changin’

Gin Lane, Meadow Lane, Lily Pond Lane, Further Lane… Just some of the fabled byways that would evoke visions of exclusive estates and pricey real estate in the minds of buyers with their real estate brokers salivating at the thought of the sizeable commissions to come. From Southampton to Amagansett, the affluent buyer and their fortunate brokers would jockey for the best properties on the ocean, bays, ponds, farm fields and villages that define the exclusive areas south of 27 (SOH). However Montauk Highway, our Mason-Dixon line, is starting to find itself besieged as less familiar roads with names such as Scuttle Hole, Day Lily, Robertson, Ferry, Deerfield and Hayground gain prominence. Indeed there is a large and growing number of buyers in the know who have discovered the many benefits and attractions of being North of the Highway.

Money, Money, Money

For years, one of the primary reasons to buy north was money. Houses and land were simply less expensive once you crossed “the Highway.” But look at these numbers… $36 million on Ferry Road, $20+ million on Day Lily Lane, $12.5 million on Cedar Street, and $9.75 million on Main Street in Sag Harbor. Those are just some of my significant NOH trades over the last decade. Suddenly “those” people who would buy North of the Highway have turned into “the” people savvy enough to pioneer the changing landscape of the Hamptons. Certainly with the resources to purchase wherever they wanted, the buyers on the streets above opted for special properties in unique locations. And the trend is bound to continue. In North Haven alone, there are four listings over $20 million, while from Southampton to Montauk, the landscape NOH is littered with other pricey properties for sale that are garnering significant attention. Still, the buyer unconcerned with proximity to the beach is finding tremendous opportunities and superlative values at prices far below its SOH counterparts. Hard pressed to find newly constructed, two acres estates with tennis South of the Highway for much less than $15 million, buyers are discovering that from Southampton to Bridgehampton, there are a variety of options available from just over $4 million to under $10 million. Looking for a nice, new house on an acre SOH for under $5 million? Don’t look on Parsonage, Hedges or Daniels Lanes in Sagaponack. Nor should you look on Ocean Road, Lily Pond or Further Lane where the starting prices are bound to be over $7 million. But, merely cross over to the other side, and options abound for new construction well below for what you could find for the same house SOH.

I Love Rock & Roll

And, rockers seem to love North of the Highway too. Mr Margaritaville, The Piano Man, Sir Paul and the Material Girl all call NOH home. Media darlings Matt Lauer, Christie Brinkley, and Alec Baldwin, as well as former Mayors Rudy Giuliani and Michael Bloombrg hang their hats well north of 27. Prominent people from all walks of life have discovered the open fields, the wooded seclusion and the broad bay fronts that define the many different areas NOH. Play golf? With the exception of the Maidstone, every 18-hole golf course IS North of the Highway, from the historic Shinnecock in Southampton to the tony East Hampton Golf course bordering the Springs and all the way to the very good and public Montauk Downs. Many Hamptonites actually plan their purchases so that the only long driving they do is from the tee.

Build It and They Will Come

When he started building on 14 Hills Court and the very northern reaches of Deerfield Road in the mid ’90s, Joe Farrell could not have imagined that only 20 years later he would be offering and selling houses from $8 million to nearly $10 million on the farm fields of Bridgehampton North. But that’s exactly what he is doing. Having just sold the first of five houses he is building on 2 acre lots with tennis within the fabled Two Trees Farm, Farrell has embraced NOH with renewed vigor offering numerous options from $3 million and up, setting the stage for other builders and developers to capitalize on the need for great, new construction at prices that could not be achieved south of 27. Want something with tennis at a price? I represent 5 houses from a variety of builders ready to go right now from just under $5 million to $6.5 million, several bordering open reserve. You’re not finding that on the other side of 27. Call me and let me show you.

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Over the past week, there were 21 Listings that went into contract from Westhampton to Montauk.




Compared to this same week last year (2025), there were 20 Listings that went into contract.




Which is a year over year INCREASE of 5%.

This same week in 2024, there were 28 Listings that went into contract.

Compared to this past week, there was a DECREASE of 25%.

Hamptons Real Estate Market Data – Week of 7/14/2026

Over the past week, there were 21 Listings that went into contract from Westhampton to Montauk.

Compared to this same week last year (2025), there were 20 Listings that went into contract.

Which is a year over year INCREASE of 5%.

This same week in 2024, there were 28 Listings that went into contract.

Compared to this past week, there was a DECREASE of 25%.

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  • Sant Ambroeus has become one of the East End’s most beloved dining destinations. The place has style, serves gelato and espresso all day, offers inviting outdoor seating, and delivers a world-class dining experience.

Their fresh pasta is made with eggs, and doesn’t weigh you down like other pasta does. The signature branzino dish has become a calling card for the Southampton location.

No visit is complete without a stop at the gelato counter, where handcrafted gelato and sorbetto are churned in-house, offering a cool, classic finish to a summer meal.

You’ll see me there again sipping an espresso and pretending to be Italian. Diet starts tomorrow.
  • Ralph’s Coffee is popping up at Mulford Farm for the summer season. Stop by from 8am - 5pm for specialty drinks, pastries, outdoor seating, and lawn games until September 7th.
@ralphscoffee 
#Popup #ralphscoffee #coffee
  • Today, @childrensmuseumoftheeastend hosted its 16th Annual Family Fair in Bridgehampton, raising funds for its on-site food pantry, providing summer camp scholarships to local children, and supporting other initiatives that serve East End families year-round.

A special thank you to CMEE and lead event sponsor Saunders & Associates for welcoming us to capture the day’s magic.
  • We stopped by Pre-Loved in Montauk to see where founder @sunnymelet sources her vintage pieces. You can visit Pre-Loved any day of the week from 10am - 6pm.
@prelovedmtk
  • Last week, Rebecca Minkoff, alongside RummiKlubLA founders Laura Galvan and Marnie Wekselblatt, celebrated the launch of their first collaboration, a limited-edition blue terrycloth RummiKlubLA game set, with a Hamptons-style game day at the picturesque Maidstone Inn in East Hampton.

The limited-edition game set features a vibrant cobalt-blue terrycloth carrying case, playing pieces, and racks featuring the signature Rebecca Minkoff logo. The set feels luxurious and is a summer essential.
@rebeccaminkoff @rummiklubla

#rummikub #rebeccaminkoff #easthampton #maidstone #collab
  • If you’re into Mediterranean cuisine, Calissa is the spot for you. From the moment you arrive, you’re greeted with complimentary valet parking, amazing front-of-house staff, and an oasis of Greek fine dining. The place runs like a jet engine: an open kitchen, sexy interior, an energetic environment, a long bar, and an enormous outdoor dining area.

We sat down and started with the Saganaki, the world-famous fried Greek cheese. They do it right at Calissa: coated in sesame seeds and drizzled with fresh honey, the dish is a flavor bomb. I recommend ordering the steak here, it comes out cooked perfectly with fresh tomatoes. We also tried the grilled octopus, which is listed as an appetizer but could easily stand in as your entrée if you’re looking to eat a little lighter that evening.

If you feel like dancing, the restaurant transforms into a lively bar after 10pm making for a real Hamptons memory. The entire evening at Calissa is special. Highly recommend.
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