Top Ten Most Expensive Homes Sold in 2019 in The Hamptons

The Hamptons is one the world’s most exclusive seaside resorts — and the ultimate playground of the rich and famous. In addition to its lush greenery and opulent vacation homes, the area is dotted with private beaches on the Atlantic coast, stretching from Southampton to East Hampton on New York’s Eastern Long Island.

The towns, hamlets and villages in this highly exclusive oasis are famed for their association with prominent figures such as former First Lady Jacqueline Kennedy Onassis and painter Jackson Pollock. What’s more, if location and accessibility are ever-paramount selling points, then the easy commute to the Hamptons from New York City — via public or private transportation — certainly satisfies that criteria.

This ideal location — coupled with amenities like panoramic ocean views, infinity pools and private golf courses — might cause you to believe that those who can afford to buy a home here would jump at the opportunity. However, our findings show that the majority of buyers shy away from splurging. In fact, homes sold below the asking prices in nine of the 10 most expensive residential sales of 2019. Keep reading for details about each of these sales in the legendary leisure hub.

#10. Historic Normandy House Sells for $2.9 Million Below Asking Price After Years of Price Changes

This historic, French chateau-style estate on the waterfront of Southampton Village’s Lake Agawam was initially listed at $24.9 million, but sold in October 2019 for $22 million — nearly $3 million below asking price. Architects Henry M. Polhemus and Lewis Augustus Coffin Jr. of New York’s prestigious Polhemus & Coffin designed the property, which was built in 1925 and once called “Chateau O’Brien” for its then-owner, attorney Kenneth O’Brien.

The home was renovated throughout 15 months by architect Oliver Cope and builder Ed Bulgin. It boasts 400 feet of water-frontage visible from the home’s majestic entry foyer and all main rooms, a waterfront pool with terraces, outdoor living spaces and a new tennis court. The lavish interiors were designed and decorated by Tony Ingrao and the gardens’ enormous lawns by landscape architect Edmund Hollander. Also, on the property is a guest cottage with its own sitting room, a staff wing, a full kitchen, two bedrooms and two bathrooms, as well as a pool house with an additional bathroom and lounge. The main home has five bedrooms, including a master bedroom with a waterfront view, and a private balcony/terrace overlooking the lawns, lake, and gardens.

#9. Legendary Bouvier Residence, Grey Gardens, sells for $2 Million Above Asking Price

The East Hampton estate at 7 W. End Ave., which was immortalized in the documentary Grey Gardens, was put on the market by owner Sally Quinn. She and her late husband, who purchased it for $220,000 from the Beales in 1979, invested approximately $600,000 in its restoration. They listed the property — which was designed in 1897 by Joseph Greenleaf Thorpe — for $19,995,000. The home sold in October for $22,050,000, more than $2 million above the asking price.

With more than 145 feet of direct ocean frontage, the 6,000-square-foot home sits on almost two acres of land, and includes: seven bedrooms; a swimming pool; a tennis court; and an 800-square-foot, two-bedroom, two-bathroom, two-level beachfront cottage with a wrap. As a protective measure for the house, a fortified dune revetment is now renovated with landscaping and a fence to guard the cottage and property from erosion. The house is in East Hampton Village on a street with easy access to the main thoroughfare and the airport.

#8. Media Mogul’s Water Mill Home Sells After Sales Price Drops $7.5 Million in Three Years

The home of prolific businessman James Mooney was first put on the market in December 2014 for $35 million, making the list of the most expensive homes for sale in the Hamptons at the time. By 2019, it was reduced to a final $27.5 million asking price and sold for $24.5 million in December — $3 million below the final asking price and a remarkable $10.5 million below its initial listing price. Justifying the steep initial price was the fact that this home not only features 360-degree panoramic views from the Atlantic Ocean to Jules Pond, but it’s also one of the only eight properties that share a one-mile stretch of pristine sandy beach.

Designed to make the most of its waterfront location, the bedrooms have circular, glass-encased designs, and all the principal rooms have beach-side terraces with ocean, dune, and pond views. The traditional estate with a majestic, double-height entry foyer has its own walkway to the ocean and luxurious amenities throughout, including: 330 feet of direct oceanfront; a library; a media room; a great room with a wet bar; a heated pool; a spa; a pool house with a bathroom and kitchenette; a professional chef’s kitchen inside; an outdoor kitchen; and an outside entertaining area with a covered terrace and media room.

#7. Former Ballerina’s 1917 Home Sells for $11 Million Below Asking Price

Built in 1917 on Sagg Pond’s waterfront in a no-flood zone, this home has had only two owners, with the final one being the legendary ballerina Sono Osato. Initially listed for more than $30 million, the house sold in May 2019 for $26 million, which, though well below the asking price, was still described as one of the Hampton’s biggest transactions of 2019. Spurring the sale was its location on historic Quimby Lane, in one of the most expensive zip codes in the country, as well as amenities such as: an ocean-view artist studio; 300 feet of water frontage on Sagg Pond; multiple fireplaces; a pool; salon-style entertaining rooms; and ocean views complemented by 180-degree views north to the bridge.

#6. After 4 Years on the Market, Great Neck Pond Sells for $5 Million Below Asking Price

Built in 2012 by Mark Himmelsbach of Ironwood Construction, and based on designs by celebrated architect John David Rose with landscaping by Ed Hollander, this house was first listed for sale at a $42.5 million asking price in 2015, according to The Wall Street Journal. The price was later lowered to $37.5 million by Bespoke, and then discounted another $5 million to a final asking price of $32.5 million. In December 2019 — in what was called one of the year’s biggest sales in the Hamptons — it sold for yet another $5 million discount at $26,972,400.

The home, a secluded waterfront on the Atlantic Ocean and Halsey Neck Pond with a traditional exterior design, was celebrated by Architectural Digest. Augmenting its luxury is 110 feet of Halsey Neck Pond water frontage and ocean views; interior and exterior fireplaces; an outdoor dining pavilion; a heated, saltwater Gunite pool; a spa; an 800-square-foot pool house; a movie theater; a library; a tennis court; an exercise pavilion; and a four-car, heated garage.

  • Address: 80 Meadowmere Lane, Southampton, NY 11968
  • Sale Price: $26,972,400
  • Number of bedrooms: 9
  • Number of bathrooms: 9+
  • 12,000+ square feet
  • 3,987 square feet (outside area – covered Mahogany Porches and balconies)
  • 3.1 acres

#5. Spectacular Old Towne Enclave Estate Sells for $9 Million Below Asking Price

So uniquely exceptional that it was featured on CNBC’s “Secret Lives of the Super Rich,” this enormous estate at 6 Olde Towne Lane built by Kean Development was the largest on the Hamptons market when it was put up for sale in July 2017 for $34.95 million. The so-called Summer House, built in 2016, ultimately sold for $27 million after a year and a half on the market.

This ultra-luxury, 23,000-square-foot estate has a three-level main house that features three full staircases, an elevator, six fireplaces, a great room, and a library. While the exterior is classic, the interior is extremely well-appointed with amenities, including: chef and family kitchens; a custom Gunite pool; a pool house with a terrace and sun shelves; tennis and basketball courts; a gym; a sauna; a steam room; a massage room; a spa room; a loggia with retractable screens; a theater; a rooftop putting green; an outdoor terrace and dining area; a three-car, detached garage; and remarkable staff quarters with their own full kitchen, sitting room and two bedrooms each with full baths.

#4. Tear-down on Billionaire’s Lane Sells for Almost $30 Million

Listed as a “tear down” with a $35 million asking price, the contemporary-style home was built in 1997 at 950 Meadow Lane. It sold for $5 million below asking price at $29,875,000 in October 2019 in an off-market deal by renowned broker James Giugliano of Nest Seekers International. In addition to beachfront, the home also features an 800-square-foot pool and a tennis court.

#3. Three-Level Mammoth Mansion Sold for $1.2 Million Below $32.5 Million Asking Price

Built by a developer who purchased the property’s 2.3 acres of land in 2005 for $10 million, this spec home became the subject of controversy due to its size of more than 10,000 square feet. Last purchased in 2011 for $21.6 million by Seacret, LLC, it sold in May 2019 to Casa Meadow, LLC for $31.4 million after initially listing for $32.5 million. This Barnes Coy-designed property at 96 Meadow Lane — one of the wealthiest streets in the Hamptons — provides spectacular views of the ocean to the south and of Cooper Pond to the north. In total, it has more than 2.3 acres of ocean frontage.

This property’s amenities are simply outstanding and include radiant heated bedrooms floors; a heated, three-car garage; a climate-controlled wine room; an elevator; a gym; a theater; a game room; and staff apartments. Expanding upon the waterfront focus of the design is a Gunite infinity pool situated ocean-side, and an ocean-facing, covered patio in the master bedroom.

#2. Multi-Structure “Three Ponds Farm” Sells for $15 Million Less Than Asking Price

Comprising eight structures — including the 25,000-square-foot Italianate main house designed by architect Allan Greenberg — the Three Ponds Farm compound has three properties and three ponds and is so large that it bestrides both Water Mill and Bridgehampton.

In fact, the property — formerly a dairy farm — is so spacious that it features a 6,307-yard, USGA-rated, 18-hole, private golf course; an over-sized pool with a pavilion; a tennis court; and grounds and gardens complete with a caretaker’s cottage, a club house, a carriage house, an orangerie, a staff suite and a pro shop. The main home has five fireplaces, exotic wood floors of cherry and mahogany, indoor-outdoor living spaces, and Venetian-plastered walls. They all lead to landscape architect Edmund Hollander’s masterful and varied gardens (rose, wildflower, etc.), fruit trees, wisteria-covered pergolas, and breathtaking grounds.

The massive property was first listed in 2003 for $75 million. By 2018, the price had been reduced to $60 million until it was finally discounted to its last asking price of $49 million. It sold in June for $34 million — a considerable discount from the original asking price.

#1. Natural Gas Billionaire Sells Oceanfront Masterpiece Near $42.5 Million Asking Price

Michael S. Smith, CEO of Freeport LNG, put up for sale his Hamptons home at 263 Surfside Drive in the hamlet of Bridgehampton for $42.5 million. It sold in June 2019 in an off-market deal for $39.3 million — just $3.3 million below the hefty asking price.

Designed by Barnes Coy Architects, the floor-to-ceiling glass windows and doors afford natural lighting and panoramic views befitting a home “surrounded on all sides by water” with views of Sag Pond and the ocean. What’s more, the infinity edged Gunite pool smoothly prolongs the waterfront theme for an uninterrupted view of water. Further enhancing the luxury of the home are amenities such as 6,000 square feet of attached deck space, two powder rooms, an outdoor living space, a pool house and spa, a roof deck, and a state-of-the art outdoor kitchen.


In order to determine the most expensive sales in the Hamptons in 2019, all residential transactions that closed between January 1, 2019, and December 31, 2019 were considered. Package deals were excluded.

Andreea Popescu

Andreea Popescu

Andreea Popescu is a copywriter with ten years of legal experience, including real estate and marketing. She is an ABA-certified paralegal and has an MBA with a concentration in Marketing from California State University, Northridge. She worked as a legal manager at a marketing firm and as a legal writer. Currently, Andreea brings her combined knowledge of the fields to report on real estate developments for CommercialEdge and PropertyShark. Reach her at [email protected].