Shelter Island, NY Homes

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  /48

  $2,895,000

  • 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 of lush

  

  Terry Thompson

  Douglas Elliman Real Estate

  (631) 800-7430

  7 Gazon Rd, Shelter Island, NY 11964
• 

  

  

  /20

  $60,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  16 Little Ram Island Dr, Shelter Island, NY 11964

  In one of the most sought after locations on Shelter Island, this original waterfront cottage has the most beautiful water views overlooking Coecles harbor to Gardiners Bay, with full sunlight from Sunrise to Sunset. This 4 bedroom 2 bath property sits at the end of a long winding driveway providing great privacy. There has been a new kitchen renovation now providing water views while cooking.

  16 Little Ram Island Dr, Shelter Island, NY 11964
• 

  $1,950,000 Sold Mar 14, 2025

  • 1,650 Sq Ft
  • $1182/SF
  • 322 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1953

  3 Sea Gull Rd, Shelter Island, NY 11964

  The ultimate sunrise and sunset views adorn this special waterfront 3 bedroom home on Mabel's Creek overlooking Shelter Island Sound and the Shelter Island South Ferry route to and from Sag Harbor's North Haven. Sit outside and renovated 2 story cottage/beach house getaway with water views from most rooms in the house on a quiet street ending at a private Shorewood Association boat launch access

  Cynthia Barrett Brown Harris Stevens Hamptons

  3 Sea Gull Rd, Shelter Island, NY 11964
• 

  Est $1,643,913 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,150 Sq Ft

  63 N Midway Rd, Shelter Island, NY 11964

  63 N Midway Rd, Shelter Island, NY 11964
• 

  

  

  /12

  $2,750,000

  • 6 Beds
  • 4 Baths
  • 2,418 Sq Ft

  14 Freds Ln, Shelter Island, NY 11964

  Tucked away on a shy acre, this private retreat features a heated Gunite pool framed by mature trees. The main house has an open floor plan with cathedral ceilings and exposed wood beams in the living room, a cook's kitchen with stainless steel appliances, island seating for 3-4, and a dining area that flows easily for entertaining. A deck off the kitchen sets the stage for alfresco dining and

  Melina Wein M WEIN REALTY INC

  14 Freds Ln, Shelter Island, NY 11964
• 

  

  /20

  $30,000 per month

  • 4 Beds
  • 4 Baths
  • 3,100 Sq Ft
  • House for Rent

  15 S Cartwright Rd, Shelter Island, NY 11964

  Located on the southern side of Shelter Island within close proximity to beaches and boating, this house has been completely renovated with all modern amenities in place. The entry porch leads you into the great room, which includes the kitchen, dining, living and lounge area. The kitchen and dining area are open plan and lead out to the pool, garden and expansive fenced garden. The bedrooms are

  Michael Brennan Douglas Elliman Real Estate

  15 S Cartwright Rd, Shelter Island, NY 11964
• 

  $3,500,000 Sold Feb 11, 2025

  • 3,225 Sq Ft
  • $1085/SF
  • 28 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1985

  44 Saint Mary's Rd, Shelter Island, NY 11964

  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,

  Michael Brennan Douglas Elliman Real Estate

  44 Saint Mary's Rd, Shelter Island, NY 11964
• 

  Est $1,354,076 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  5 Emerson Ln, Shelter Island, NY 11964

  5 Emerson Ln, Shelter Island, NY 11964
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  /15

  $3,175,000

  • 3 Beds
  • 2 Baths
  • 1,373 Sq Ft

  13 Tarkettle Rd, Shelter Island, NY 11964

  Nestled on over an acre along Shelter Island's coveted Dickerson Creek, this Scandinavian-style waterfront cottage offers a serene escape with 100 feet of gorgeous shoreline. Imagine waking up to breathtaking sunrises and launching your paddleboard right from your backyard!Inside, discover a light-filled comfortable floor plan enhanced by Swedish-inspired decor. The home features three bedrooms

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  13 Tarkettle Rd, Shelter Island, NY 11964
• 

  

  /25

  $50,000 per month

  • 5 Beds
  • 6 Baths
  • House for Rent

  37 Tuthill Dr, Shelter Island, NY 11964

  WHEN AN ARTIST MAKES A HOME Serena Dugan, Co-Founder of Serena&Lily has completed her renovation of 37 Tuthill Drive, Shelter Island. This property is a robust representation of Serena's vision as an artist and a designer. Each detail was carefully considered and selected, and her point of view is visible throughout the house. The artwork, fabrics, and wallpapers are of her design. In some

  37 Tuthill Dr, Shelter Island, NY 11964
• 

  $2,500,000 Sold Feb 11, 2025

  • 2,774 Sq Ft
  • $901/SF
  • 16 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1973

  18 Dickerson Dr, Shelter Island, NY 11786

  , Additional information: Interior Features:Guest Quarters,Marble Bath

  Michael Brennan Douglas Elliman Real Estate

  18 Dickerson Dr, Shelter Island, NY 11786
• 

  Est $2,967,000 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  12 Terry Dr, Shelter Island, NY 11964

  12 Terry Dr, Shelter Island, NY 11964
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  /12

  $2,795,000

  • 4 Beds
  • 4.5 Baths
  • 5,300 Sq Ft

  10 Sunshine Rd Unit B, Shelter Island, NY 11964

  Quintessential Hamptons estate in the heart of Shelter Island . Enjoy the best of both worlds at this traditional Hamptons style home, with approximately 5000sqft of immaculate living space across one level, and nearly an acre of land, it's the perfect setting for the best of year round and seamless indoor-outdoor living. The custom-built home welcomes you with its vaulted ceiling in the foyer,

  Adam Hofer Douglas Elliman Real Estate

  10 Sunshine Rd Unit B, Shelter Island, NY 11964
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  /31

  $18,000 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
• 

  $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
• 

  Est $2,837,000 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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  /35

  $3,200,000

  • 4 Beds
  • 4 Baths
  • 3,420 Sq Ft

  156 Ram Island Dr, Shelter Island, NY 11964

  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

  Mary Elizabeth Galle Corcoran

  156 Ram Island Dr, Shelter Island, NY 11964
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  /29

  $20,030 per month

  • 5 Beds
  • 5 Baths
  • 3,874 Sq Ft
  • Condo for Rent

  13 Brander Pkwy Unit ID1014115P, Shelter Island, NY 11964

  Welcome to Sandpoint, an exclusive Shelter Island retreat nestled on 1.4 acres, just a stone's throw from a sandy beach and across from a 12-acre preserve. This stunning home features five bedrooms, including two master suites and one room with twin beds. Sunlit and spacious, the heart of the home is a well-equipped kitchen with an oversized island overlooking a large pool and landscaped grounds.

  13 Brander Pkwy Unit ID1014115P, Shelter Island, NY 11964
• 

  $1,050,000 Sold Jan 24, 2025

  • 2,460 Sq Ft
  • $427/SF
  • 153 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1993

  1 Deer Park Ln, Shelter Island, NY 11964

  Escape to tranquility in this beautiful contemporary home nestled on Shelter Island. Built in 1993, this 3-bedroom, 3.5-bathroom residence boasts 2,460 square feet of meticulously crafted living space, perfectly positioned to capture breathtaking water views from nearly every room. Upon entry, you're greeted by the inviting ambiance of the great room, featuring a majestic gas fireplace and

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  1 Deer Park Ln, Shelter Island, NY 11964
• 

  Est $5,056,696 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
• 

  

  /5

  $3,995,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  47B S Ferry Rd, Shelter Island, NY 11964

  Discover a secluded paradise on Shelter Island, nestled within the expansive 2,350-acre Mashomack Nature Preserve. Tucked away at the end of a private road lies a unique opportunity: 1.74 acres of picturesque land featuring a charming 1,800 square-foot home with three bedrooms. Enjoy breathtaking water vistas from every window, 150 feet of direct water frontage, and the convenience of a private

  Hedgerow Exclusive Team Hedgerow Exclusive Properties

  47B S Ferry Rd, Shelter Island, NY 11964
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  /29

  $14,000 per month

  • 4 Beds
  • 2 Baths
  • 1,720 Sq Ft
  • House for Rent

  3 Lakeview Dr, Shelter Island, NY 11964

  Wake up each morning to the sweet sounds of birdsong in this charming 4-bedroom, 2-bath, nestled amongst rolling hills. Located .6 miles from coveted Wades Beach and Mashomack Preserve. This secluded property feels like a private sanctuary, surrounded by lush greenery, blooming trees, and vibrant summer flowers. The open-concept living-dining-kitchen area is perfect for entertaining, with a

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  3 Lakeview Dr, Shelter Island, NY 11964
• 

  $710,000 Sold Dec 18, 2024

  • Land
  • 1.00 Acre
  • $710,000 per Acre

  • 39 Days On Market

  3 N Cartwright Rd, Shelter Island, NY 11964

  Build Your Dream Home On This Magnificent, Level, Buildable Lot Near Town Dock And Coecles Inlet. Board Of Health Approved & Plans Allow For A 4000 Plus Square Foot Home On The Site.

  Scott Bennett Douglas Elliman Real Estate

  3 N Cartwright Rd, Shelter Island, NY 11964
• 

  Est $1,104,622 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,726 Sq Ft

  105 S Ferry Rd, Shelter Island, NY 11964

  105 S Ferry Rd, Shelter Island, NY 11964
• 

  

  /38

  $4,950,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,040 Sq Ft

  104 S Ferry Rd, Shelter Island, NY 11964

  This exceptional south-facing two-story home is nestled on 3.44 acres, offering breathtaking panoramic views of lush lawns, towering mature trees, a serene pond, and a charming barn. The front yard features a circular driveway and a double-arched covered porch with a beautiful bluestone patio. Inside, the entryway leads into a bright dining room and a spacious living room, both adorned with

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  104 S Ferry Rd, Shelter Island, NY 11964
• 

  

  /16

  $55,000 per month

  • 5 Beds
  • 4 Baths
  • House for Rent

  4 Bay Ave, Shelter Island, NY 11964

  This clean and modern harborfront home is located in an area that features glorious sunsets. There are lovely gardens and shade trees with meditation areas to read or relax in, and the main home offers an open floor plan, with an L-shaped living room that maximizes views of the water, a fireplace for chilly nights, dining area overlooking the water, and efficient kitchen. There is a first floor

  4 Bay Ave, Shelter Island, NY 11964
• 

  $1,237,500 Sold Nov 20, 2024

  • 81 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1979

  79A N Midway Rd, Shelter Island, NY 11964

  Don't miss this exceptional opportunity and great value to own a special slice of heaven down a private lane close to Shelter Island Country Club, Sunset Beach, Shopping, Restaurants and more. This 4 Bedroom 2 1/2 Bath sits on over 1.2 beautiful acres with mature trees and expansive lawns Creating a peaceful retreat. Room for majestic pool and guest house. Has attached garage and full basement

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  79A N Midway Rd, Shelter Island, NY 11964
• 

  Est $787,000 Not Listed For Sale

  169 N Ferry Rd, Shelter Island, NY 11964

  169 N Ferry Rd, Shelter Island, NY 11964
• 

  

  /29

  $2,145,000 Open Sat 12PM - 1:30PM

  • 3 Beds
  • 3 Baths
  • 1,897 Sq Ft

  40 Dinah Rock Rd, Shelter Island, NY 11964

  Picture a rural drive through farm fields and vineyards to a short ferry boat ride from Greenport's harbor, then a scenic meander along Shelter Island's picturesque coves. Continue passing through a golf course and arrive at your home in Hay Beach, across the street from a sandy shoreline with a magnificent sunset and bay views directly in front of your home. This could be you this year. The 1900

  Caroline Sarraf Compass

  40 Dinah Rock Rd, Shelter Island, NY 11964
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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
• 

  $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
• 

  Est $2,192,000 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
• 

  

  /35

  $1,990,000

  • 3 Beds
  • 2 Baths
  • 3,170 Sq Ft

  27 Country Club Dr, Shelter Island, NY 11964

  Nestled in the desirable and tranquil Hay Beach neighborhood, this elegant Traditional home was lovingly crafted by a local artist in 2011. Spanning 3,170 square feet, the residence offers a seamless blend of craftsmanship, comfort, and modern convenience. Designed to maximize natural light, the home features vaulted ceilings, radiant floor heating, and a striking stone fireplace, creating a warm

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  27 Country Club Dr, Shelter Island, NY 11964
• 

  

  /20

  $23,000 per month

  • 4 Beds
  • 3 Baths
  • House for Rent

  71 Gardiners Bay Dr, Shelter Island, NY 11964

  Beautiful home across the street from beach access, relax and unwind in this 4 bedroom 3 bath home steps to beach. Back deck off the dining room for additional entertaining space. Additional playroom on the lower level. The kitchen and baths are recently updated. [[Rental Registration # 2025-V0002]]

  71 Gardiners Bay Dr, 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
• 

  Est $1,395,000 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
• 

  

  /22

  $1,085,000

  • 3 Beds
  • 2 Baths

  26 Ole Buck Run, Shelter Island, NY 11964

  This recently renovated 3 bedroom, two bath home with wood burning fireplace is situated on .89 private acres. The home now has a: new roof, siding, and air conditioners. Newly refinished floors, painted interior, new back decks, exterior basement entry and new appliances. Turn key and ready for you to enjoy for Summer 2025.

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  26 Ole Buck Run, Shelter Island, NY 11964
• 

  

  /10

  $50,000 per month

  • 3 Beds
  • 2 Baths
  • 1,691 Sq Ft
  • House for Rent

  21 Peconic Ave, Shelter Island, NY 11964

  Impeccable cottage ideally located in the heart of Silver Beach. Very Closeto the secluded association beach and a short distance to Shell Beach. Lovely deck with water view and cool summer breezes. Three bedrooms and two bath. Ref. R103 MD - LD $50,000 June - LD $50,000, June $10,000, July $20,000, and August $25,000

  Melina Wein M WEIN REALTY INC

  21 Peconic Ave, Shelter Island, NY 11964
• 

  $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 $972,000 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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