The 5 Most Expensive Homes for Sale on Long Island – Summer 2021

We all know that Long Island can be expensive, but the price of these homes in the Hamptons and the North Shore “Gold Coast” will blow you away. Here we tour the 5 most expensive homes for sale on Long Island, which unsurprisingly are all waterfront homes and feature beautiful beaches, pools, tennis courts, and all the amenities you could imagine.

1. 30 Mathews Rd, Wainscott, NY 11975 – $70 million

Most expensive homes for sale on long island - Wainscott East Hampton

This one-of-a-kind, spectacular estate on nearly 14 bucolic acres boasts more than 800 feet of water frontage and stunning views of Georgica Pond and the Atlantic Ocean. The long, winding driveway transports you to a private, serene world with parklike grounds, including lush rolling lawns and perfectly manicured mature specimen plantings. The elegant 10,000 SF+/- residence was built in 2010 by renowned local builder Ben Krupinski and designed by noted architect Paul Rice.

A gracious double-height entry foyer gives way to a formal dining room with fireplace. There is an adjacent open kitchen with breakfast area and a family room with French doors flowing into a screened porch and a long, covered porch, designed to blend indoor and outdoor living space. The first floor also comprises a stately library with fireplace, living room, sunroom with full wet bar ideal for large gatherings and entertaining, and an en-suite staff or guest bedroom. The second floor features five en-suite bedrooms, including the spacious master suite, which has a large walk-in closet, master bath with double sink vanity, soaking tub and shower, sitting room with fireplace, and a private balcony with awe-inspiring views.

The finished lower level offers open recreation space, a home theater, gym with steam shower, along with a seventh bedroom and the ability for an eighth bedroom. The pastoral grounds include a detached three-car garage, pool house and heated Gunite pool that overlooks Georgica Pond. All this, along with the ability to subdivide creating potential for a second waterfront estate, with room for another residence complete with a pool, pool house and tennis court. A unique and unparalleled Hamptons opportunity.

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2. 201 Lily Pond Lane, East Hampton, NY 11937 – $69 million

Generational opportunity on Lily Pond Lane offered for the first time in 75 years. Originally built in 1925 and named Cima Del Mundo (top of the world) this handsome Spanish colonial style gem underwent design renovation in 1994 by William Hodgins. The property boasts 2.7 acres with 400 feet of ocean frontage with commanding views toward fabled Georgica beach. Look north across Lily Pond with with protected views enhanced by the only Ha-Ha wall in East Hampton.

The residence consists of 8 bedrooms 7.5 baths. A grand yet inviting interior is designed for the ultimate indoor/outdoor living. The gracious entry foyer with impeccable tile work and striking curved stairway introduce the refined finishes throughout. Rounding out the interior include a large eat in kitchen, 5 fireplaces, study, double height living room and 3.5 car garage. Exterior features include oceanside pool, pool house, and extensive terraces and second floor deck taking full advantage of the panoramic views including spectacular sunsets over lily pond. Come experience this one of a kind offering at this prestigious Lily Pond Lane address.

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3. 33 Lily Pond Ln, East Hampton, NY 11937 – $64 million

Located on one of the world’s most coveted streets, this oceanfront oasis boasts unobstructed views of the Atlantic Ocean and gorgeous white sand beaches with 175 +/- feet of private ocean frontage. Perched on a double revetment dune and surrounded by beautifully manicured grounds, the main residence offers 7,000 +/- square feet with six bedrooms, eight bathrooms, a chef’s kitchen, and ocean views from both the first and second level. Set on 1.8 +/- acres, the compound affords a pool and spa, situated between the main house and separate pool house, with immaculately manicured grounds displaying perennial gardens and a koi pond.

The six room, three bathroom pool house presents an entertaining area equipped with kitchen, game room, sauna, and steam shower. Located adjacent to the pool house is tennis, which is the only lit private court in East Hampton. With a private approach accessed by only two other homes, this pristine oceanfront offering affords the utmost in seclusion and location.

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4. Undisclosed Address, Great Neck, NY 11024 – $55 million

Most expensive home for sale in Nassau County Long Island

Situated on 8+ Acres of sprawling waterfront property with unobstructed views of the bridges and the New York City skyline, Three Bridges is one of the last remaining generational properties on Long Island’s Gold Coast. The Compound boasts 3 separate estate homes, a deep water dock, 100’+ waterfront pool/hot tub, tennis court, multiple gardens, multiple indoor pools, a lazy river, multiple spas, a movie theater and more.

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5. 346 Meadow Ln, Southampton, NY 11968 – $52.5 million

Situated on one of the most prestigious streets in The Hamptons, 346 Meadow Lane is a once-in-a-lifetime opportunity for a unique estate on the highly-coveted Hamptons shoreline. This beachside home has the air of an English countryside cottage with its rounded, wood-shingled roof reminiscent of thatching, but boasts an impressive 5,000+ square-feet of contemporary living on 200 feet of pristine beach frontage. The home shares its esteemed Meadow Lane address with a number of prominent estates owned by celebrities, CEOs and Wall Street executives, on one of the most secluded and exclusive pieces of shoreline in The Hamptons.

Designed by the prominent architectural team of Beyer Blinder Belle of Met Breuer museum and Empire State Building fame, the home has interiors by the late Andrée Putman, renowned French designer. The home is currently owned by Phyllis Pressman, wife of late Barneys New York Chairman Fred Pressman, who was the son of Barney’s founder, Barney Pressman.

The exterior of the home embodies old-world charm and feels like it was peeled off the pages of a fairy tale, while the interior is a master-class in contemporary comfort. A dramatic spiral staircase leads to a second floor with an open concept living area, a large terrace and a dining room with fireplace. The three-story interior features banks of windows in circular bays, a gourmet chef’s kitchen and stunning ocean views, while outside the pool terrace, extensive decks and wrap-around porches provide for endless opportunites for outdoor, seaside living.

The finishes in the seven bedroom estate exude luxury oceanside sensibility – soft, white-washed wood accents complement clean gray and white stone, and touches of metal accent both. Natural light flows through each living space thanks to generous windows and sprawling open-concept design. A 53-foot pool, tennis court, two-car garage with an artist studio and inviting circlular drive complete this distinctive coastal estate.

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