Shelter Island Heights, NY Homes

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  /43

  $1,999,000

  • 6 Beds
  • 4 Baths
  • 4,949 Sq Ft

  61 Gardiners Bay Dr, Shelter Island Heights, NY 11965

  Investors Dream! Welcome to this expansive 6-Bedroom, 4-Bath Home with Water Views on Shelter IslandThis spacious 6-bedroom, 4-bathroom home, nestled in one of Shelter Island’s most sought-after locations, offers a perfect blend of luxury and comfort. Featuring a grand primary suite and a versatile junior suite, it’s ideal for both relaxation and hosting guests.The very large dining

  

  Marie Catanzano

  Signature Premier Properties

  (844) 791-3908

  61 Gardiners Bay Dr, Shelter Island Heights, NY 11965
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  /19

  $28,500 per month

  • 4 Beds
  • 2 Baths
  • House for Rent

  185 N Ram Island Dr, Shelter Island, NY 11964

  Set on 1.8 acres of bay front on Ram Island. House has 4 bedrooms, 2 bathrooms, sleek modern beach cottage decor, and has forever views onto Gardiner's Bay. The property is set up for gracious outdoor summer living, including a wall of sliding doors from living room, formal dining room and master suite overlooking the bluff, kitchen with granite countertops, vaulted ceiling, fireplace, infinity

  185 N Ram Island Dr, Shelter Island, NY 11964
• 

  $2,500,000 Sold Aug 14, 2025

  • 1,674 Sq Ft
  • $1,493/SF
  • 233 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  5 Bay Shore Dr, Shelter Island Heights, NY 11965

  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

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  5 Bay Shore Dr, Shelter Island Heights, NY 11965
• 

  Est $1,432,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  75 W Neck Rd, Shelter Island Heights, NY 11965

  75 W Neck Rd, Shelter Island Heights, NY 11965
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  /48

  $2,895,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,901 Sq Ft

  7 Gazon Rd, Shelter Island, NY 11964

  Immerse yourself in the serene charm of 7 Gazon Road, a Zen-inspired retreat tucked away on Shelter Island. This waterfront sanctuary offers the perfect balance of modern luxury and tranquil living. With three bedrooms and two-and-a-half baths, you can choose between a first or second-floor primary suite, each thoughtfully updated to exude sophistication and comfort. Nestled on 1.6 acres

  

  Terry Thompson

  Douglas Elliman Real Estate

  (631) 800-7430

  7 Gazon Rd, Shelter Island, NY 11964
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  /11

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • House for Rent

  3 Saint Johns St, Shelter Island Heights, NY 11965

  Set on a peaceful street in Shelter Island’s historic Heights neighborhood, this furnished mid-century modern home has everything you need for an enjoyable year round rental. There’s plenty of room to spread out, a spacious deck for lounging or dining outside, and a grill ready for cookouts. You’re just a few blocks from shops, restaurants, and all the local action. As a bonus, you’ll have access

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  3 Saint Johns St, Shelter Island Heights, NY 11965
• 

  $1,450,000 Sold May 30, 2025

  • 1,854 Sq Ft
  • $782/SF
  • 20 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1967

  5 Wade Rd, Shelter Island, NY 11964

  Situated far back from the road and offering privacy and tranquility, a long driveway leads to this move-in ready, super comfortable expanded ranch nestled on a landscaped .62-acre lot and loaded with updates ~ A spacious tiled entry hall welcomes you into the home and leads you to the open-concept main area ~ Gleaming quartz counters add a stylish touch to a well-equipped kitchen complete with

  Rosanna Piazza Signature Premier Properties

  5 Wade Rd, Shelter Island, NY 11964
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  Est $2,678,000 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,450 Sq Ft

  6 Behringer Ln, Shelter Island, NY 11964

  6 Behringer Ln, Shelter Island, NY 11964
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  /36

  $5,950,000 Open Thu 11:30AM - 1:30PM

  • 5 Beds
  • 4.5 Baths
  • 3,206 Sq Ft

  5 N Menantic Rd, Shelter Island, NY 11964

  A rare offering on Shelter Island, this waterfront estate represents a legacy of architectural pedigree and enduring luxury. Built in 1860 and renovated over the years, the home is a singular blend of history and Hamptons elegance, set on nearly 3 acres with western-facing water views, a deepwater dock, and every hallmark of refined coastal living. In an iconic Shelter Island location on West

  Myles Reilly Saunders & Associates

  5 N Menantic Rd, Shelter Island, NY 11964
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  /27

  $50,000 per month

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • House for Rent

  28 Gardiners Bay Dr, Shelter Island Heights, NY 11965

  Experience the ultimate in tranquility and luxury at this secluded oasis, where every moment is a picturesque escape. Discover breathtaking panoramic water views and soak in the mesmerizing sunrise & sunsets over Gardiner's Bay from just about every room in the house. Boasting an impressive layout featuring an open plan den/media room, dining room, and chef's kitchen-all thoughtfully designed to

  Michael Brennan Douglas Elliman Real Estate

  28 Gardiners Bay Dr, Shelter Island Heights, NY 11965
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  $975,000 Sold May 20, 2025

  • 1,472 Sq Ft
  • $662/SF
  • 174 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  1 Rebel Rd, Shelter Island, NY 11964

  Discover this inviting Ranch-style home just blocks from the sandy shores of Bootlegger's Alley beach and breathtaking sunsets. Inside, you'll find an open-concept floor plan featuring a country kitchen, dining area, living room, and den, perfect for both everyday living and entertaining guests. Cozy up by the wood-burning fireplace or relax on the spacious deck overlooking serene views and

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  1 Rebel Rd, Shelter Island, NY 11964
• 

  Est $5,279,734 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  6 Club Dr, Shelter Island, NY 11964

  6 Club Dr, Shelter Island, NY 11964
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  /38

  $5,995,000

  • 6 Beds
  • 5.5 Baths
  • 6,824 Sq Ft

  55C Shore Rd, Hampton Bays, NY 11946

  Waterfront Compound with 2 DocksLocated on one of the most prestigious beaches on all of Shelter Island is this expansive compound with all the amenities one would want. 332 +/- sandy beach and two docks, breathtaking sunset views from all major rooms, 4 lots, including underwater ownership totaling 1.31 acres, multiple waterfront decks, 4 car garage, game room, regulation size indoor racquet

  Beth Marano Corcoran

  55C Shore Rd, Hampton Bays, NY 11946
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  /25

  $25,000 per month

  • 3 Beds
  • 3 Baths
  • 1,675 Sq Ft
  • House for Rent

  5 Bay Ave, Shelter Island, NY 11964

  Open plan beach house with superb water views located in the highly sought after Montclair Colony. Centrally located near markets and many conveniences, there is much to adore in this home. Open plan living room with sunroom, dining and eat in kitchen. This home offers two bedrooms with two full baths and another bedroom with a full bath over the two car garage. In addition the master bedroom has

  Michael Brennan Douglas Elliman Real Estate

  5 Bay Ave, Shelter Island, NY 11964
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  $1,250,000 Sold Feb 07, 2025

  • 2,380 Sq Ft
  • $525/SF
  • 304 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1986

  5 Country Club Dr, Shelter Island, NY 11964

  Nestled on 1.06 acres of serene beauty, this charming ranch-style home offers the perfect blend of comfort and coastal living. Enjoy easy access to pristine beaches, world-class golf courses, and all the amenities Hay Beach has to offer. Inside, you'll find a spacious and inviting interior with hardwood floors, vaulted ceilings, and a skylight-lit eat-in kitchen. The primary suite features a

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  5 Country Club Dr, Shelter Island, NY 11964
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  Not Listed For Sale

  39 Gardiners Bay Dr, Shelter Island Heights, NY 11965

  39 Gardiners Bay Dr, Shelter Island Heights, NY 11965
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  /45

  $4,500,000

  • 4 Beds
  • 7 Baths
  • 5,500 Sq Ft

  139 A N Ferry Rd, Shelter Island Heights, NY 11965

  Welcome to this exceptional custom-built home nestled on 1.1 secluded acres, offering the perfect blend of luxury, comfort and privacy. Hidden at the end of a long driveway, the main house boasts 3 bedrooms and 3.5 bathrooms. The 1st floor main suite features include double doors that open to a private deck, a WIC and an expansive master bathroom equipped with a spa style rain shower. To add to

  Annmarie Seddio Atlas Sales Realty

  139 A N Ferry Rd, Shelter Island Heights, NY 11965
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  /35

  $75,000 per month

  • 6 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • House for Rent

  15 Montclair Ave, Shelter Island, NY 11964

  Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a

  Margot Reutter Corcoran

  15 Montclair Ave, Shelter Island, NY 11964
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  $1,850,000 Sold Oct 29, 2024

  • 2,628 Sq Ft
  • $704/SF
  • 96 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2005

  45 New York Ave, Shelter Island, NY 11964

  No details spared in this impeccably renovated Village Classic 4-bedroom spacious home with water views of Chase Creek in the heart of Shelter Island Heights and down the street from shops, restaurants, The Chequit Hotel, Eccentric Bagel, Stars Caf?, Marie Eiffel, Leon 1901, Sunset Beach, Shelter Island Golf Club and more. The first floor graciously flows from the living room with new raised

  David Tenenbaum Brown Harris Stevens Hamptons

  45 New York Ave, Shelter Island, NY 11964
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  Est $799,000 Not Listed For Sale

  169 N Ferry Rd, Shelter Island, NY 11964

  169 N Ferry Rd, Shelter Island, NY 11964
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  /16

  $4,900,000

  • 3 Beds
  • 3 Baths
  • 2,061 Sq Ft

  68 Peconic Ave, Shelter Island, NY 11964

  Shelter Island Sound water front beach house offers stunning sunsets, sandy beach, fully bulkheaded, L'Shaped dock with lift and splash boards;a waterside 50' heated Gunite pool; and expansive unobstructed views out to Robins Island. A serene retreat with a blend of comfort and coastal charm nestled on .75 acres. Designed for relaxation as well as easy entertaining, with a straightforward layout

  Melina Wein M WEIN REALTY INC

  68 Peconic Ave, Shelter Island, NY 11964
• 

  $2,515,000 Sold Oct 18, 2024

  • 2,800 Sq Ft
  • $898/SF
  • 96 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2017

  8 Crescent Way, Shelter Island, NY 11964

  Located in a desirable area of Shelter Island known as Hay beach, This traditional home is ready for it's new owner. The home offers an open floor plan with vaulted ceilings, a chef's kitchen with a large island and dining area. The master suite offers substancial closets, double sinks with a large shower with a bench seat. The two additional bedrooms share a bathroom, the second floor has a

  Christine Beckwith Douglas Elliman Real Estate

  8 Crescent Way, Shelter Island, NY 11964
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  Est $3,635,333 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft

  31 Terry Dr, Sag Harbor, NY 11963

  31 Terry Dr, Sag Harbor, NY 11963
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  /20

  $4,000,000

  • 3 Beds
  • 3 Baths
  • 1,626 Sq Ft

  100 Peconic Ave, Shelter Island, NY 11964

  Infinite Views over Shelter Island Sound and extensive bulk-headed sandy beach front make for perfect, summer days and sunset filled nights spent enjoying the beauty and tranquility of this property. Charming interior with beautiful wood floors and touches of wainscoting, living room with beamed cathedral ceiling, picture window and wood burning fireplace, cooks kitchen with dining alcove, two

  Melina Wein M WEIN REALTY INC

  100 Peconic Ave, Shelter Island, NY 11964
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  $1,579,000 Sold Oct 10, 2024

  • 1,637 Sq Ft
  • $965/SF
  • 390 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1985

  16 Great Circle Dr, Shelter Island, NY 11964

  Modern luxury meets tranquility in Hay Beach. This exceptional 3-bedroom, 3-bath Modern Ranch nestled in Hay Beach's wooded haven offers an escape from the ordinary. Step inside and be greeted by an open floor plan, seamlessly connecting the living room, dining area, and a chef's dream kitchen. High-end appliances from Bosch, Liebherr, and Viking shine within custom Levante wood cabinetry and

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  16 Great Circle Dr, Shelter Island, NY 11964
• 

  Est $3,672,000 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,350 Sq Ft

  148E N Ferry Rd, Shelter Island, NY 11964

  148E N Ferry Rd, Shelter Island, NY 11964
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  /11

  $3,695,000

  • 6 Beds
  • 4.5 Baths
  • 4,229 Sq Ft

  3 Bayview Ave, Hampton Bays, NY 11946

  Sited on one of the highest points on the island, this home offers magnificent panoramic views everywhere you turn. Well-appointed with 4 bedrooms, 3.5 baths, elevator, eat-in chefs kitchen, formal dining room, living room with fireplace. Expansive decks, and heated Gunite pool offer unobstructed water views. Separate Guest house with 2 bedrooms, bath and sitting room. Heat: Oil/Hot Air, SI Town

  Melina Wein M WEIN REALTY INC

  3 Bayview Ave, Hampton Bays, NY 11946
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  $2,475,000 Sold Oct 02, 2024

  • 1,795 Sq Ft
  • $1,379/SF
  • 307 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  3 Bevan Place, Shelter Island, NY 11964

  Shelter Island Heights Waterfront Property ! This contemporary 3-bedroom home with stunning sunset and water views, perched above trees, is fantastic place for someone looking for a serene and picturesque setting. Decks surrounding the living areas providing plenty of outdoor spaces for relaxation and entertainment. The bright and open living room with a fireplace, dining room, and eat-in

  Mary Elizabeth Galle Corcoran

  3 Bevan Place, Shelter Island, NY 11964
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  Est $1,525,000 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,270 Sq Ft

  10 Penny's Path, Shelter Island, NY 11964

  10 Penny's Path, Shelter Island, NY 11964
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  /24

  $3,600,000

  • 4 Beds
  • 2.5 Baths
  • 2,890 Sq Ft

  24 Rocky Point Rd, East Marion, NY 11939

  This architecturally distinctive home, inspired by the mid-century California Case Study Houses and designed by AC Hocek, is set on two acres of gently sloping land in the prestigious estate area, "Greenlawns". Designed with a thoughtful balance of form and function, the property includes a main house and a separate guest house, offering a unique blend of modern design and natural

  Penelope Moore SAUNDERS & ASSOCIATES

  24 Rocky Point Rd, East Marion, NY 11939
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  $999,999 Sold Sep 13, 2024

  • 1,411 Sq Ft
  • $709/SF
  • 100 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1992

  36 Rocky Point Rd, East Marion, NY 11939

  Discover this custom-built contemporary home nestled on 1.47 acres of serene beauty. Crafted with love, it boasts cedar siding, wide plank pine floors, and hand-hewn timbers. Approach the meandering driveway, greeted by vibrant gardens and majestic trees-a perfect outdoor oasis. Inside, soak in the timeless charm of pine floors and abundant natural light. A passive solar design ensures energy

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  36 Rocky Point Rd, East Marion, NY 11939
• 

  Est $1,427,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,217 Sq Ft

  1 Worthy Way, Shelter Island, NY 11964

  1 Worthy Way, Shelter Island, NY 11964
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  /42

  $1,795,000

  • 4 Beds
  • 3.5 Baths
  • 1,702 Sq Ft

  26 S Menantic Rd, Shelter Island, NY 11964

  Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  26 S Menantic Rd, Shelter Island, NY 11964
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  $2,000,000 Sold Sep 12, 2024

  • 1,296 Sq Ft
  • $1,543/SF
  • 73 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1953

  74 Peconic Ave, Shelter Island, NY 11964

  Enjoy this original 1953 waterfront summer cottage with southwest prevailing breezes. The deck and covered porch are great for entertaining off the main living areas. This home is situated on .46 acres and offers original wood panelled walls and vaulted ceilings with oak floors throughout. The living room has a wood burning fireplace and open floorplan. This property is being sold "As Is". There

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  74 Peconic Ave, Shelter Island, NY 11964
• 

  Est $2,072,736 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,228 Sq Ft

  1 Country Club Dr, Shelter Island Heights, NY 11965

  1 Country Club Dr, Shelter Island Heights, NY 11965
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  /34

  $1,350,000 Open Sun 12:30PM - 2PM

  • 4 Beds
  • 3 Baths
  • 2,618 Sq Ft

  1 Gazon Rd, Shelter Island, NY 11964

  This enchanting Shelter Island home feels like a true getaway. Tucked into a peaceful setting, it offers a sense of calm and ease the moment you arrive. The house has a warm and welcoming atmosphere, with open, airy spaces that invite you to slow down and unwind. A large living room and kitchen create the heart of the home, centered by a wood-burning fireplace - perfect for gathering with friends

  Kristy Naddell Douglas Elliman Real Estate

  1 Gazon Rd, Shelter Island, NY 11964
• 

  Est $1,550,000 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,098 Sq Ft

  27 Terry Dr, Shelter Island, NY 11964

  27 Terry Dr, Shelter Island, NY 11964
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  /8

  $1,475,000

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  1 Meadow Place, Shelter Island, NY 11964

  Nestled off the road for added privacy this updated home offers Chase Creek water views. Featuring 2 bedrooms and 2 renovated bathrooms, the layout includes an office perfect for remote work or creative pursuits. The open-concept living and dining area is bright and inviting, flowing into the renovated kitchen with modern finishes and storage. Step out onto the back deck thru sliders from the

  Melina Wein M WEIN REALTY INC

  1 Meadow Place, Shelter Island, NY 11964
• 

  Est $1,503,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,860 Sq Ft

  1 Behringer Ln, Shelter Island, NY 11964

  1 Behringer Ln, Shelter Island, NY 11964
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  /6

  $750,000

  • Land
  • 1.20 Acres
  • $625,000 per Acre

  8 Wheeler Rd, Shelter Island, NY 11964

  Design Your Luxury Island Estate.Seize the rare opportunity to create your custom dream home on this pristine, level lot nestled in one of Shelter Island’s most desirable locations. Moments from the serene shores of Crescent Beach and the tranquil waters of Wades Beach, this property offers both privacy and proximity to the best of island living.Enjoy effortless access to Sunset Beach’s

  Nicholas Planamento William Raveis New York LLC

  8 Wheeler Rd, Shelter Island, NY 11964

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