The 20 Most Expensive Homes On Long Island

Long Island has long been the summer resort for wealthy New York businessmen and celebrities. Since the early 19th century, homes and estates built in prominent areas of Long Island have been inspired by the Jazz age, famed architects of the mid-twentieth century and modernists.

With exclusive areas and waterfront views, Long Island continues to be home to the rich and famous.

Here are the 20 most expensive homes on Long Island.

1. 60 Further Lane, East Hampton – $147 million

This East Hampton estate last sold for $147 million in 2014. It consists of 3 parcels on the ultra exclusive Further Lane. The main home was built by investment financier Christopher H. Browne and his architect partner Andrew Gordon and features luxury rooms throughout with great attention to design detail.

The current owner is Barry Rosenstein a New York hedge fund manager. The parcels total 18 acres and the main house overlooks the ocean. Separated by trustee owned sand dunes, the estate offers amazing views of the ocean. The property includes a private drive, a luxurious pool and several beautiful gardens. A large private pond with a foot bridge and 4 piers offers tranquil space to enjoy the water.

2. 100 Briar Patch Rd. – $140 million

Situated on 11 acres, this home located in the exclusive Georgica Pond region of East Hampton is the most expensive home on Long Island and the fifth most expensive home in the United States.

The Georgian Revival home was designed by architect Peter Marino and built in 1931 as the “Shephard Krech House”. The home was remodeled in 1990 and a 3500 square foot guest house was built on the property.

The 10,a square foot home features a 3 story living room, 10 bedrooms and 10 bathrooms, a gourmet kitchen and a third floor gym. Unique details of the home include handmade wallpaper, stenciled ceilings, reclaimed floorboards and French doors opening onto a porch in all ground floor rooms.

The grounds feature a private pond, a pool and sun deck with a changing cabana, a tennis court, and a 4 car garage. The waterfront home has beautiful views and has easy access to sailing, kayaking, canoeing and paddle boarding.

3. Kings Point Russian Palace – $100 million

The main house on this estate was built in 1928 and was recently owned by Russian emerge Tamir Sapir who remodeled the estate as a Russian palace filled with modern amenities. There are 2 other homes situated on the 8 acre waterfront property, all inspired by a Russian palace.

The living space totals 60,000 acres with a total of 13 bedrooms and 38 bathrooms. The main house has an indoor and an outdoor pool with a lazy river and swim up bars as well as a tennis court.

The property features a 2 level garage, bowling alley, racquetball court, yoga studio and a Turkish bath. The gardens are Japanese and English inspired. The estate overlooks the Long Island Sound and has views of the Manhattan skyline.

4. “Villa Maria” Water Mill – $85 million

Known as “Villa Maria”, this Water Mill, Hamptons home is steeped in history. It was built in 1881 as a summer home for a group of industrial financiers. The group purchased a windmill from Connecticut to add to the mansion’s ambience.

In 1919, Frank Freeman extensively remodeled the home. “Villa Maria” passed as a private residence but was once a convent. Shoe designer Vince Camito renovated the home again before he passed away in 2015. The home sits on 15 acres and is eclectically designed. Originally a Queen Ann style home, it features Beaux Arts, Neo-Classical and Colonial Revival architecture.

The home has a large rotunda, a soaring 3 story spiral staircase, 11 bedrooms and 12 and 1/2 bathrooms with imported Carrara marble. The grounds feature a luxury pool, carriage house and amazing views.

5. Kings Point, Nassau County – $85 million

Situated on 8 acres of waterfront property, this estate has 3 homes and many amenities. The Kings Point estate is located at the northern tip of Long Island. The estate was built in 1928 and has been updated.

There are a total of 18 bedrooms and 24 full bathrooms as well as 8 half bathrooms in the homes located on the estate. Amenities include a 250 foot private deck, several wine cellars and saunas, a tennis court, indoor and outdoor pools, a lap pool, a bowling alley and a game room.

6. 38 Matthews Rd., Wainscott – $75 million

This beautiful estate was built in 2000 and was featured in Architectural Digest. The home is 18,000 square feet with a 2 story entry hall and details including 200 year old flooring.

There are 8 fireplaces, 8 bedrooms, 12 full bathrooms and 3 half baths. There is an beautiful wine cellar and tasting room. The house has water views throughout and the grounds have a pool and tennis court. The home offers privacy within a gated community.

7. 290 Further Lane, East Hampton – $69 million

The Francis Fleetwood designed home is 10,000 square feet harmoniously blended with the landscape and ocean views. The transition includes outdoor patios with connecting porticos overlooking manicured gardens and a pool sitting on 6 acres of property.

The house has a spacious gourmet kitchen with modern appliances, Calcutta marble and attention to every detail. There is an indoor spa room with a hot tub and endless current pool. With 7 bedrooms and 9 1/2 bathrooms, the master bedroom features a beautiful fireplace with a hand carved mantle as well as his and her bathrooms.

8. 160 Ox Pasture, Southampton – $59 million

Situated on pristinely landscaped 9 acres of land this original country home was built in 1915. The 18,000 square foot mansion has updated modern amenities. There is an indoor pool with a slide housed in an open atrium as well a luxurious outdoor pool. There are also tennis and racquetball courts and a gym on site. A quaint carriage house sits on the property. This mansion is an amazing estate in a private setting.

9. Halsey Lane, Bridgehampton – $59 million

Architect Joe Farell built this amazing 30,000 square foot home in Bridgehampton with many amenities. The home sits on a beautifully landscaped private lot. There is a gourmet kitchen, 9 bedrooms and 11 bathrooms.

The home has a mini movie theater that seats 10, a bowling alley and squash court as well as a gym with a full spa including a hot tub and sauna. Fun for everyone, the playroom has a DJ booth and the basement has a rock wall. There is a pool house and heated pool as well.

10. Southampton Modern Estate – $59 million

This ultra modern Southampton home was designed by architect Frank Gehry and was once home to publisher John Randolph Hearst, one of William Randolph Hearst’s sons. The 6500 square foot home was built in the 1980s and has 7 bedrooms, 7 and 1/2 bathrooms and a salon.

The property sits on 15 acres and overlooks Lake Agawam. There is a pool, cabana and tennis court on the property. There is also a lawn sculpted as a golf fairway with imported grass.

11. 6 Bayview Court, Sag Harbor – $50 million

Located on 6 and 1/2 acres, “Angel View” estate features a 12,000 square foot home and 500 acres of waterfront. The secluded home is located in a private gated community and was built in, 1995. The home has 6 bedrooms, 6 full bathrooms and 2 1/2 bathrooms.

There are 7 fireplaces, a chef’s kitchen and a wine cellar. The estate has indoor and outdoor infinity pools, rolling landscape with bluffs dropping to the beach. There is a covered harbor cabana perfect for enjoying water activities and sunsets. This home features a sound system throughout the grounds and is built for private parties or larger ones.

12. Bridgehampton Italianate – $50 million

This beautiful Italianate villa was designed with attention to detail. The large home is filled with modern amenities yet retains its quaint Italian villa feel. The estate is beautifully gardened and includes a formal rose garden. There are breathtaking views from the home and property. The property is located on a private golf course. It features a pool, pool house and tennis court with grass. There is also a caretaker’s home located on the property.

13. 42 Old Montauk Highway – $48 million

This estate is situated on 36 acres of oceanfront property in a secluded and exclusive section of Montauk. The 7000 square foot home was designed by architect Frank Hollenbeck and influenced by a Chinese Tea House.

It features an Asian inspired blue tile roof. The home has 5 spacious bedrooms and 5 bathrooms. There is a pool and a movie theater on site. The private property is situated on a bluff overlooking the Atlantic Ocean and has tranquil gardens and walking paths.

14. 612 Halsey Lane, Bridgehampton – $43 million

Known as “The Sandcastle” this estate is a magnificent summer home. Built in 2008, the 25,000 square foot home is situated on over 2 and 1/2 acres of property. There are 10 bedrooms and 12 bathrooms.

The home features walnut floors and a grand foyer. There is a fireplace located in the formal dining room. A spacious chef’s kitchen and butler’s pantry feature the best kitchen appliances. There is a pool and sauna as well as a 10 seat theater and squash and racquetball courts and a 2 lane bowling alley. A lounge features rock climbing wall, skateboard pipe and a media room.

15. Water Mill Mansion – $38.5 million

Located in the quaint and exclusive Water Mill section of Long Island, this palatial manor 6 acres including waterfront and docking space on Mecox Bay. A gravel driveway reaches the home and is ornamented by a 4 story windmill.

The Georgian style home was designed by W.E. Brady and retains many of its original features including lead pain windows, wainscoting, columns and balusters. Two stories of verandas and decks give spectacular views of the Bay. The 5 bedroom estate includes a pool, tennis court and guest house.

16. Further Lane Modern Oceanfront – $38 million

Built in 1992, this modern oceanfront home sits on 3 and 1/2 acres. It features a domed observatory with a retractable metal roof. The home’s clean and simple lines that let in an abundance of natural light. An infinity edged pool, tennis court and koi pond add to the luxurious tranquility of the property. There is also a private boardwalk to the ocean.

17. Tower Hill, North Bridgehampton – $30 million

Super model Christy Brinkley has long been a staple of the Hamptons. Her North Bridgehampton estate known as “Tower Hill” is worth $30 million. The home is built around a 100 year old 50 foot observation tower and sits on 20 acres of pristine Long Island property.

The home encompasses over 11,000 square feet and has 9 bedrooms, 7 bathrooms and 4 partial bathrooms. There is a barn/artist studio with living space as well as a 4 bedroom guest house. The main home has a multi-level terrace and beautiful lawn with walking paths and a private pond. There is gym, pool and tennis court on site.

18. 38 Two Mile Hollow Road, East Hampton – $29.5 million

Located off of East Hampton’s exclusive Further Lane, This Hampton’s style house is a true retreat. It sits on 3 acres of oceanfront property and includes a bungalow on the beach. The home has 8 bedrooms and 9 and 1/2 bathrooms as well as 5 fireplaces throughout the meticulously decorated home. The grounds feature an infinity edged pool, tennis court and cabana, and covered outdoor seating area.

19. Sands Point Manor – $21 million

Sands Point is located on the Cow’s Neck peninsula of the northern tip of Long Island. Homes at Sands point enjoy ocean and Manhattan views. This manor is stately and majestic.

The home sits on over 19 acres of pristine land and is a charming 5800 square foot manor filled with luxury details in flooring, ceiling and wall design. There are 2 guest cottages and a brick barn on the property as well as a pool, tennis court and running track.

20. Mecox Farm Estate 850 Mecox Rd., Water Mill – $21 million

The Mecox dairy farm and home is located in the exclusive Water Mill section of Long Island. Architect James Michael Howard designed the home to blend in with the beauty of the farm. The 13,000 square home overlooks the Mecox Bay and farms.

The home has 7 bedrooms, 8 bathrooms and 5 fireplaces. There is a mahogany mantle and a glass paneled wine tasting room. The home has clean and fresh lines and amenities equal to a luxury farm house. Along with gardens and an orchard there is an infinity edged pool.

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