Top 1%: The 10 most expensive houses for sale in the booming Hamptons

Top 1%: The 10 most expensive houses for sale in the booming Hamptons

  • 06/16/21

The Hamptons real estate market continues to thrive. Unlike other upscale areas, supply is keeping up with demand – just. The luxury sector (the top 10% of the market) comprises the most expensive houses in the Hamptons, and shows no signs of dampening.

Top brokers in the area cite a handful of reasons for the white-hot sector. Some put it down to retirees selling, making the most of the aggressively priced, frenzied market. Others attribute it to new properties, ready to hit the market from development projects.

The most expensive house in the Hamptons on JamesEdition? This $78 million Southampton oceanfront property. At the more wallet-friendly end of the scale is this one-bedroom penthouse in the heart of Southampton village at just shy of $5 million. In total, we currently have a massive 937 homes for sale in the Hamptons, highlighting the booming market.

A whopping 70% of those 937 properties have a pool, 48% feature a fireplace, 11% come complete with a tennis court, and 25% boast glorious views out to the water.

The average price per listing is $2.8 million, buying wealthy investors or home seekers this newly built detached four-bedroom home in Sag Harbor village, equating to $10,000 per square meter. For around the same price tag, there’s this three-bedroom architectural masterpiece in East Hampton.

Other remarkable and expensive residences in the area that aren’t on sale currently (but have been in recent years) include Henry Ford’s house on the Jule Pond estate. Sold in April 2021 at close to its asking price of $145, the 45-acre plot boasts nearly a quarter of a mile of ocean frontage.

And then there’s junk bond billionaire Ira Rennert’s Hamptons mansion in Long Island. Construction began in the late 90s, and Rennert moved into his new home called Fair Field in 2004. Think 29 bedrooms, 39 bathrooms, a trio of pools, and a 164-seat theater, on 63 acres of prime Hamptons beachfront.

Inside, you’ll find 62,000 square feet of space. The biggest house in the Hamptons? Valued at just under $250 million back then, today the property would list for around $500 million.

We’ve rounded up JamesEdition’s top 10 most expensive houses in the Hamptons, giving a flavor of what’s currently up for grabs for those with deep pockets.

JamesEdition’s top 10 most expensive and impressive houses in the Hamptons

10. Privacy and glorious Atlantic vistas in East Hampton, NY

Price: $18,500,000

Address: 22 Terbell Lane, East Hampton, NY 11937, New York

Just a 10-minute walk from Main Beach and a 15-minute stroll from Main Street sits this contemporary property in East Hampton. The detached three-story home lies in a two-acre landscaped plot and boasts 9,000 square feet of internal space. With six bedrooms and 11 bathrooms, enjoy beautiful views out to the Atlantic and a sense of privacy. And you’re only a five-minute drive from Maidstone Golf Club.

Designed by architectural firm Botta Sferrazza, enter via the gates and head up the long flag driveway before reaching the impressive house. The thoughtfully conceived interiors feature an elevator, an entertainment roof, a theater, 20-foot ceilings in the main room, five fireplaces, and a detached garage. A top-quality kitchen, geothermal heating, Alabama limestone patios, and an infinity pool with spa complete with picture.

9. A gated 15,200 square feet estate in Southampton, NY

Price: $25,000,000

Address: 275 Ox Pasture Road, Southampton, NY 11968, New York

Here you have the Tenacre Estate, spread across 15,200 square feet. This shingle-style home in Southampton is less than a five-minute drive from the beach and sits on three well-manicured mature acres. Originally commissioned in 1920, architect John Russell Pope took the project on, combining informality and livability. The nine-bedroom 12-bathroom space has been expanded and revamped over the decades.

Through the gates and along the winding drive, you’ll then reach the main entrance. With indoor-outdoor areas aplenty, there’s uninterrupted flow and attention to detail, from one-of-a-kind finishes and floor-to-ceiling French doors to the wine room, laundry chute, and staff quarters. The kitchen boasts marble counters and professional stainless steel appliances, while the garage features lifts and accommodates six vehicles. There’s also an indoor pool with lap lanes, as well as a sauna.

8. Original features galore and an eye-catching façade in Southampton, NY

Price: $25,000,000

Address: 172 South Main St, Southampton, NY 11968, New York

Stroll for 15 minutes and you’ll reach Gin Beach from this 12-bedroom house in Southampton village. Built back in the 1860s heyday of 19th-century Hamptons summer society, the ocean is close by and the residence itself has been renovated top to bottom. Think original lead glass windows, stained hardwood floors, wainscoting, and paneling. Spread over three levels, the next owners will enjoy a porte cochère, covered porches and verandas, and 10 bathrooms.

Gated and hedged for full privacy, the eye-catching façade gives way to moldings, millwork, and meticulously plastered walls. Outside in the glorious sculpted garden, there’s an inviting swimming pool, an outdoor fireplace, and a built-in barbeque – the ideal entertaining space.

7. Direct waterfront across 659 feet and a cove-facing pool in Water Mill, NY 

Price: $35,000,000

Address: 263 Olivers Cove Road, Water Mill, NY 11876, New York

This fabulous 4.6-acre residence in Hayground Cove boasts 12,000 square feet of interior space spanning eight bedrooms and seven bathrooms. Situated at the end of a cul de sac, the home features more than 650 feet of direct waterfront, plus a dock and an all-weather tennis court. Head down the private drive and you’ll reach the wood-sided property with a cedar roof.

An impressive foyer gives way to light-filled living spaces and a wall of French doors looking out to the lawn and cove-facing pool. Up the sweeping staircase you’ll find the generous en-suite master complete with a sitting room and deck. Staff areas and an attached garage round things off. Water Mill is less than five minutes away by car, but why would you want to leave this picturesque spot?

6. Strongheart Manor: 14,000 square feet and a dozen bathrooms in Sag Harbor, NY

Price: $44,000,000

Address: Sag Harbor, NY 11963, New York

Situated on the waterfront, this 12-bedroom property in North Haven sits in a seven-acre plot spread across a trio of separate lots – the main house goes by the name Strongheart Manor. With 14,000 square feet and a dozen bathrooms, the family detached home looks out to Peconic Bay and Mashomack Preserve. Highlights include a substantial direct bay frontage and a private deep water dock, as well as a sandy beach and a waterfront pond.

The gated residence exudes privacy and tranquility, yet it’s a mere five minutes from quaint Sag Harbor, known for world-famous boating. Built in 1902, the property has been totally refurbed and modernized by Bulgin and Associates while retaining charm. There’s a screened-in porch, several entertaining spaces, and multiple fireplaces. And outdoors? A sizeable pool, rolling lawns, and a basketball court.

5. A rare opportunity to purchase waterside ‘Ocean Dream’ in Southampton, NY

Price: $49,999,999

Address: 5 Fair Lea (aka 36 Gin Lane), Southampton, NY 11968, New York

A stone’s throw from the beach sits ‘Ocean Dream’, this waterside estate in Southampton. With three floors, nine bedrooms, and 12 bathrooms (three partial), the 7,660 square feet space is on the market for the first time in decades. The oceanfront residence sits in a 3.7-acre plot and boasts a pool and a grass tennis court. Head down the private drive just off renowned Gin Lane and you’ll be wowed by the attractive shingle-style home.

Expect covered porches and decks wrapping the first and second levels, offering indoor-outdoor living and entertainment space aplenty. Just a 15-minute amble from the center of Southampton and the same by car to National Golf Links of America, the house also features media and sunrooms, a formal dining area, a butler’s pantry, and an oversized dine-in kitchen. Open the French doors overlooking the putting green and gaze out to the ocean. Back indoors, there’s a workout room, staff quarters, and a three-car garage.

4. Architecturally impressive and overlooking the ocean in Wainscott, NY 

Price: $49,500,000

Address: 115 Beach Lane, Wainscott, NY 11975, New York

This detached beachfront house in Wainscott sits on three acres and boasts 11,000 square feet of space indoors across six bedrooms and 11 bathrooms. Behind a gated entrance, the architecturally impressive property overlooks the ocean and features tempered glass, granite, and zinc. Just a 15-minute walk from the center of the hamlet, the four-floor stucco and teak residence was built by Mayfair Construction and furnished by Julia Roth Designs.

Comprising three separate pavilions integrated from within by passageways and staircases, highlights include a 22-foot ceiling Great Room, a media room, an expansive gym, a spa bath with steam and sauna, a golf simulator, and a four-car garage. Outside, there’s an eccentrically shaped deck and pool, a large covered area complete with an outdoor kitchen, a dining table, and a seaside living room, plus pristine landscaping by LaGuardia Design Group. Stroll along the private walkway and over the dune to picture-postcard Wainscott Beach where sunbathing, body surfing, and nighttime bonfires await.

3. A waterfront family home looking out to Cooper’s Beach in Southampton, NY

Price: $52,500,000

Address: 346 Meadow Lane, Southampton, NY 11968, New York

With a prime Meadow Lane address, this beachside property in Southamptonoverlooks Cooper’s Beach and is a 10-minute drive from Sebonack Golf Club. Close to the village center, Main Street, and Jobs Lane, the magical property was designed by renowned architect firm Beyer Blinder Belle and decorated by the esteemed Andrée Putman.

The stucco beachfront detached family home sits on three acres and covers 5,926 square feet inside across three floors, seven bedrooms, and eight bathrooms. With 200 feet of frontage, enjoy wonderful waterside vistas, and convenient access to the beach beyond the private dune. What else? A pool for dipping in and lounging around, an alfresco covered dining area, a tennis court, a two-car garage, plus terraces and decks galore.

2. Grand and capacious, sitting on 10 acres of manicured land in Southampton, NY

Price: $75,000,000

Address: 160 Ox Pasture Road, Southampton, NY 11968, New York

Grandiose and sprawling are two words to describe this 18,000 square feet masterpiece in Southampton. One of the most expensive houses in the Hamptons we have listed, think 12 bedrooms and 15 bathrooms with original features, three floors, and separate staff quarters. In 10 acres of manicured land, there’s park-like privacy as well as two pools – one outside, another indoors.

Additionally, there’s a spa, a well-kept grass tennis court, a paddle court, and a duo of pavilions with full kitchens for outdoor dining. Other features include a circular fountain, a carriage house with a connecting greenhouse, and a pair of detached four-car garages. Location-wise, you’re just a couple of kilometers from Cooper’s Beach and the center of the village. Oh, and Friar’s Head golf course is just a 30-minute drive away.

1. A 14-bedroom home with 360-degree views of the water in Southampton, NY

Price: $78,000,000

Address: 1080 & 1100 Meadow Lane, Southampton, NY 11968, New York

Currently the most expensive Hamptons listing on JamesEdition, this oceanfront property in Southampton also overlooks Shinnecock Bay, making it a house with 360-degree views of the water. Built in 1994, the style is traditional and the position is prime. Spread across 5,000 square feet, the 14-bedroom and 19-bathroom house offers more than eight acres of land with direct access to the beach across two separate lots.

The trophy location is close to Southampton, and the nine-acre plot includes a tennis court, an outdoor pool, a pair of golf greens, and a three-car garage. If you want to get more golf in, Shinnecock Hills Club is just a 10-minute drive away. Back at the house, step along one of the private walkways to the Atlantic and enjoy unobstructed views in two directions.


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