24 Properties in The Hamptons

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47 S Ferry Road
$9,900,000

Shelter Island, NY
House
Bedrooms: 4
Bathrooms: 4
Web ID: 3521653

In our beloved 2,350 acres of Mashomack Nature Preserve, there are a handful of residences. At the end of this long private road through this preserve, one can find this breathtaking newly constructed modern home with no details left behind. This expertly crafted home is loaded with premium amenities, top-of-the-line appliances, and walls of windows overlooking Coecles Harbor, this home has no comparisons. With 3,800 sq. ft., the home features an open floor plan with sweeping water views from every vantage point, whether dining, cooking, or lounging. Continue entertaining outside on the large outdoor waterfront deck where you become one with nature. The master and one of the guest bedrooms are en-suite, and the 2 additional bedrooms share a bath. All the bedrooms have abundant closet storage. This home is one of the winners of The Sara National Design Awards 2024.

Tina Marika Kaasik
(4018626607) ) ) ) ) ) ) ) ) )

97 Westmoreland Dr
$7,950,000

Shelter Island, NY
House
Bedrooms: 6
Bathrooms: 5
Web ID: 3567654

Step into a piece of history with this beautifully restored Tudor home, originally built in 1901. Meticulously maintained and updated with modern amenities, this 6-bedroom, 4.5-bathroom residence offers the perfect blend of classic charm and contemporary comfort. Inside, you'll find 6 stunning fireplaces, each equipped with heatilators for efficient warmth. The original plaster has been carefully restored, preserving the home's historic character. New heating and central air conditioning systems ensure year-round comfort, while additional insulation on the second and third floors provides energy efficiency. A chef's dream, the kitchen has been completely renovated and features a newly added butler's pantry. Outside, the property boasts a heated 20x50 Gunite pool and hot tub, perfect for entertaining and relaxation. A classic brick patio complements the elegant surroundings, and a deep water dock accommodates multiple boats, making this the ideal waterfront retreat.

Linda L McCarthy
(6317491155) ) ) ) ) ) ) ) ) )

8 Cove Way
$5,995,000

Shelter Island, NY
House
Bedrooms: 4
Bathrooms: 5
Web ID: 3578053

This stunning, fully renovated waterfront home features 4 bedrooms and 5 baths, with year-round blooming gardens. It boasts 113 feet of waterfront, a stone patio with a firepit, and a Gunite heated pool surrounded by lush landscaping for privacy. Perched on a bluff, winding stairs lead to a dock with 4.5 feet at low tide. The home includes two primary suites with water views, two guest suites, a living room with cathedral ceilings, a large kitchen and dining area, a full bath, and a media room. All rooms offer views of the stone patio and water. Ready for immediate move-in. Schedule a viewing soon.

Patrick J McLaughlin
(6317250200) ) ) ) ) ) ) ) ) )

156 Ram Island Drive
$4,200,000

Shelter Island, NY
House
Bedrooms: 4
Bathrooms: 3.5
Web ID: 3577201

Surrounded by preserved land this classic home has an absolutely magnificent setting that includes stunning water views. The open kitchen, breakfast room and family room creates a comfortable bright living area that walks out to a lovely patio overlooking Gardiners Bay . The more formal dining and living room with fireplace also provides amazing views of the water. The spacious primary bedroom with balcony is as dreamy as the view, which is truly incredible. An oversized bath and additional upper-level bedroom complete this private owner's area. Two main level bedrooms serviced by a full bath will accommodate family and friends beautifully. A two-car garage and studio with a half bath is a great place to set up your game room or home office. A full basement with high ceilings can be finished to incorporate an exercise or workout room. Lush landscaping with charming stone walls...

Mary E Galle
(2032167272) ) ) ) ) ) ) ) ) )

7 Stearns Point Road
$3,995,000

Shelter Island, NY

Bedrooms: 9
Bathrooms: 9
Web ID: 3569658

Step into timeless elegance with this iconic single-family residence with an option for an owner-occupied 5-bedroom bed & breakfast (B&B) license. Originally constructed in 1902 and beautifully reimagined to meet modern standards. Nestled in the serene Shelter Island Heights, 7 Stearns Point Road offers an exquisite blend of historic charm and contemporary luxury. This expansive property sits on a 0.70- acre parcel, equipped with 5,838 +/- sq. ft. of living space, plus a spacious basement level adding 2,588 +/- sq. ft. The property features 7 ensuite bedrooms complemented by 2 large living rooms and a well-appointed kitchen. Recent renovations have expanded the living space to include an extension with 2 additional bedrooms, a stunning double-height Great Room, as well as a state-of-the-art gym/yoga studio. Enjoy the beautiful backyard with a heated 40x18 in-ground Gunite pool, perfect for relaxing after a day exploring the nearby Crescent Beach and...

Nikola Cejic
(6316048323) ) ) ) ) ) ) ) ) )

Contract Signed
Property for Sale at 44 St Marys Road, Shelter Island, Hamptons, NY - Bedrooms: 3 
Bathrooms: 4  - $3,900,000 Previous PhotoNext Photo

44 St Marys Road
$3,900,000

Shelter Island, NY
House
Bedrooms: 3
Bathrooms: 4
Web ID: 3560589

Limited opportunity for this special property! Unique Shelter Island opportunity to find 8.5 acres with unobstructed scenic views that will leave you speechless. This classic property is currently being utilized as a horse farm, with a 3 bedroom main house, 3 stall horse stables, a barn and a pool house/garage with studio and full bath above. The main house features 3 en-suite bedrooms, kitchen, living room, dining room, a den/sunroom off the primary suite and a large mudroom with laundry. The second floor features two large en-suite bedrooms and a bonus room. With all this land, this is a great opportunity to reimagine the current home or to bring your architect and create your own dream. Located in C Residential zone, the possibilities are endless, with subdivision opportunities and full development rights. This property and all of its surrounding land promise a lifestyle of unparalleled beauty, adventure, and...

Michael Brennan
(9176643017) ) ) ) ) ) ) ) ) )

5 Bay Shore Drive
$3,300,000

Shelter Island, NY
House
Bedrooms: 3
Bathrooms: 2
Web ID: 3590276

This waterfront home with deep water dock is a boater's dream. A cozy beach home featuring 3 bedrooms, 2 full baths, a 2 car garage, and outdoor shower, all tucked down a quiet dead-end road, in the sought after Silver Beach area. Enjoy breathtaking sunrises from this spacious yard overlooking West Neck Creek, and a nature preserve. This wonderful home is near the most desirable beaches on Shelter Island.

Tina Marika Kaasik
(4018626607) ) ) ) ) ) ) ) ) )

4 Gazon Road
$3,200,000

Shelter Island, NY
House
Bedrooms: 6
Bathrooms: 5
Web ID: 3554498

Move in and immediately enjoy this elegant Colonial home on an expansive parklike property with all the amenities you have dreamed of. The bright, open and airy main floor features 9 foot ceilings. a spacious living room with wood burning fireplace, gourmet kitchen with high end appliances and large ground floor primary suite. Outside enjoy multiple outdoor living destinations; entertain on the living room like bluestone covered front porch, lounge by the heated gunite pool with travertine surround, enjoy a good book or barbecue on the back deck or relax with friends around the firepit. A short distance down the private road is your private waterfront parcel complete with a large dock perfect for launching your power boat, paddleboards and kayaks or enjoying sunset and docktails on your floating lounge. The second floor of the home is perfectly appointed for family and guests with four generously sized...

Peter H Humphrey
(6463442759) ) ) ) ) ) ) ) ) )

5 Hagar Road
$2,745,000

Shelter Island, NY
House
Bedrooms: 3
Bathrooms: 3
Web ID: 3564455

Experience the epitome of coastal living in this meticulously maintained one-level home, nestled in a charming beach community. Renovated in 2012 by Fokine Construction, this stunning residence offers breathtaking water views of Menantic Creek from nearly every room. Inside, you'll find an open-concept floor plan featuring a vaulted living room with a cozy fireplace, a dining area, and a custom chef's kitchen. Step outside onto the waterside deck, adorned with mahogany railings and stainless wire, for a serene outdoor retreat. The primary bedroom is a true oasis, complete with two walk-in closets and a luxurious en-suite bathroom. Enjoy the tranquility of the 1.29-acre shared parcel extending into the creek. This quiet enclave offers the perfect blend of luxury and natural beauty, making it an ideal coastal retreat.

Debra L Von Brook Binder
(6317491155) ) ) ) ) ) ) ) ) )

4 Irene Lane
$2,655,000

Shelter Island, NY
House
Bedrooms: 4
Bathrooms: 3
Web ID: 3543543

Discover a serene sanctuary amidst the natural beauty of Shelter Island. This stunning residence offers breathtaking water views of Miss Annie's Creek, providing an unparalleled escape from the ordinary. Step onto the property and be captivated by the charm of covered porches and a heated pool, inviting you to relax and soak in the picturesque vistas. Whether you're enjoying a quiet morning coffee or hosting unforgettable gatherings, this waterfront oasis provides the perfect backdrop for every occasion. Don't miss this opportunity to own a piece of paradise in Mashomack Preserve.

Tina Marika Kaasik
(4018626607) ) ) ) ) ) ) ) ) )

Contract Signed
Property for Sale at 18 Dickerson Drive, Shelter Island, Hamptons, NY - Bedrooms: 4 
Bathrooms: 4  - $2,495,000 Previous PhotoNext Photo

18 Dickerson Drive
$2,495,000

Shelter Island, NY
House
Bedrooms: 4
Bathrooms: 4
Web ID: 3549391

Michael Brennan
(9176643017) ) ) ) ) ) ) ) ) )

3 Crab Creek Road
$2,100,000

Shelter Island, NY
House
Bedrooms: 3
Bathrooms: 3
Web ID: 3557181

This split level home with 1.47 acres is located in the silv er beach area of Shelter Island. When you walk into the home you are invited into the main room of the home with large vaulted ceilings and an open airy concept. There are 2 bedrooms with 2 bathrooms on the upper level and 1 bedroom and bathroom on the lower level. The backyard has a large heated gunite pool to enjoy with a pool house that has a living room, half bathroom and a gym. The added bonus to this property is that it has a tennis/basket ball court which is hard to find on Shelter Island.

Christine M Beckwith
(6313548100) ) ) ) ) ) ) ) ) )

Shelter Island
$2,050,000

Shelter Island, NY
House
Bedrooms: 4
Bathrooms: 4.5
Web ID: 907035

Don't miss the chance to own a piece of Hamptons paradise with this new construction at a price to sell! Designed and built by Award winning Hamptons Architectural Firm London Architecture + Design. The home features 4 ensuite bedrooms with room for King-sized beds. Situated in a quiet neighborhood, just a 5 minute walk from West Neck Bay, and Bootlegger Alley Beach. This brand new 4 bedroom, 4.5 bath room home is currently under construction for summer 2024! The well-thought-out open floor plans includes a custom modern European kitchen with LP gas range and 8' island facing a dining and living room with wood burning fireplace. A wall of 8' tall glass sliding doors open up to an expansive mahogany deck and in-ground pool. The lower level is finished with 9' ceilings and glass sliding doors opening up to an areaway and OSE with lots of natural light. A...

Cristina Matos
(631) 204-2408

8 Tims Trail
$1,975,000

Shelter Island, NY
House
Bedrooms: 4
Bathrooms: 5
Web ID: 801164

Situated in a quiet neighborhood, just a 5 minute from West Neck Bay, and Bootlegger Alley Beach. This 4 bedroom, 4.5 bath room home is turnkey and ready for your decorator! The home features 4 ensuite bedrooms with room for King-sized beds. The open floor plans includes a custom modern European kitchen with LP gas range and 8' island facing a dining and living room with wood burning fireplace. A wall of 8' tall glass sliding doors open up to an expansive mahogany deck and private yard. The lower level is finished with 9' ceilings and glass sliding doors opening up to an areaway and OSE with lots of natural light. A separate single car garage with aluminum and glass door has plenty of attic storage! Finished with wide plank European white oak floors, Andersen Windows, Fiber Cement, and Mahogany siding. Appliances: Range BuildingAreaSource: Other, InteriorFeatures: Soaking Tub,

Jonathan Minerick
(8884002513) ) ) ) ) ) ) ) ) )

Shelter Island
$1,950,000

Shelter Island, NY
House
Bedrooms: 5
Bathrooms: 3
Web ID: 909434

Enter by way of a circular drive to this Designers own fabulous reconstruction and renovation of the Classic and Iconic Captain Cartwright House handsomely landscaped in Shelter Island. This classic 5 bedroom home, detached garage, covered porches, blue stone patios and heated 20 x 40 gunite pool with all the bells and whistles is centrally located between the South and the North Ferries and across the street from the 2350 acre Mashomack Preserve on Shelter Island. The very private setting is ideal for relaxing by the chic lounging areas around the pool or entertaining summer guests on the beautifully landscaped grounds perfect for intimate dinners. An oversized outdoor shower is a show stopper. Dine at the many new and established restaurants including Leon 1909, Vine Street Cafe, 1901, The Pridwin, The Chequit, Rams Head Inn, Isola, Sunset Beach, Marie Eiffel, Stars Cafe and Eccentric Bagel and more on the island....

Cynthia R Barrett
(631) 537-4322

72 S Ferry Road
$1,950,000

Shelter Island, NY
House
Bedrooms: 1
Bathrooms: 1
Web ID: 3565240

Nestled amidst rolling lawns, woods, and a stocked pond, this serene 5.5-acre property offers the ultimate in privacy and tranquility. A 1,000-foot private driveway leads you to this expansive estate, where endless possibilities await. The property features a spacious artist's studio with a wall of windows on the first floor and a separate apartment above, providing ample space for both work and living. Enjoy the elegant elevated in-ground pool, offering stunning views of the surrounding natural beauty. Conveniently located less than a mile from South Ferry and a short distance to Wades Beach and Mashomack Preserve, this property offers the perfect blend of seclusion and accessibility.

Linda L McCarthy
(6317491155) ) ) ) ) ) ) ) ) )

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