Shelter Island, NY Homes

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  $4,800,000

  • 5 Beds
  • 3.5 Baths
  • 3,325 Sq Ft

  90 Peconic Ave, Shelter Island, NY 11964

  Held by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured - a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved. Custom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island shingled beach house sits on a level acre along one of the

  

  Elizabeth Melichar

  Serhant East End LLC

  90 Peconic Ave, Shelter Island, NY 11964
• Explore Shelter Island

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  /20

  $40,000 Per Month

  • 4 Beds
  • 4 Baths
  • House for Rent

  56 N Menantic Rd Unit B, Shelter Island, NY 11964

  Welcome to a beautifully designed modern retreat in Shelter Island, where architecture, comfort and nature come together seamlessly. This four bedroom, four bathroom home offers approx. 2,300 sq ft of thoughtfully curated living space, set on a private, landscaped property. The home showcases a clean, contemporary design with warm natural materials, soaring ceilings and expansive windows that

  Claire Evans Compass

  56 N Menantic Rd Unit B, Shelter Island, NY 11964
• 

  $1,140,000

  Sold Jul 20, 2026

  16 Shelterlands Path, Shelter Island, NY 11964

  • 3 Beds
  • 3 Baths
  • 1,950 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Below List Price
  • $585/SF
  • 58 Days On Market

  Last Listing Agent Mary Elizabeth Galle Corcoran

  16 Shelterlands Path, Shelter Island, NY 11964
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  Est $2,074,713

  Not Listed For Sale

  45 New York Ave, Shelter Island, NY 11964

  • 4 Beds
  • 4 Baths
  • 2,628 Sq Ft
  • Built 2005

  45 New York Ave, Shelter Island, NY 11964

  Last Sold Summary

  • 96 Days On Market

  Last Listing Agent David Tenenbaum Brown Harris Stevens Hamptons
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  /50

  $1,350,000

  • 2 Beds
  • 2 Baths
  • 1,464 Sq Ft

  11 Jaspa Rd, Shelter Island, NY 11964

  Welcome to your private Shelter Island retreat, where comfort, character, privacy, and exceptional outdoor living come together. This inviting 2-bedroom, 2-bath home offers thoughtfully designed spaces, beautiful hardwood flooring throughout, and an impressive collection of amenities for year-round living or the perfect island escape. The well-appointed kitchen features a refrigerator,

  

  Karen Neglia

  RustyCap O Inc

  11 Jaspa Rd, Shelter Island, NY 11964
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  /31

  $20,000 Per Month

  • 4 Beds
  • 2 Baths
  • 1,850 Sq Ft
  • House for Rent

  9 Johnston Rd, Shelter Island, NY 11964

  Shelter Island 4 Bedroom Cottage with Gunite Pool and Hot TubAn enchanting mid-century cedar-shake ranch with a new heated Gunite pool, separate outdoor hot tub, outdoor shower, cedar deck, pea-gravel driveway, hammock, and propane bbq grill. Four bedrooms and two full baths. The house has a breezy nautical theme and a large record collection with great four-speaker sound and an upright

  Isaac Halpern Brown Harris Stevens Hamptons

  9 Johnston Rd, Shelter Island, NY 11964
• 

  $2,679,000

  Sold Jan 21, 2026

  156 Ram Island Dr, Shelter Island, NY 11964

  • 4 Beds
  • 4 Baths
  • 3,420 Sq Ft
  • Built 1995

  Last Sold Summary

  • 36% Below List Price
  • $783/SF
  • 446 Days On Market

  Current Estimated Value $2,995,289

  Last Listing Agent Mary Elizabeth Galle Corcoran

  156 Ram Island Dr, Shelter Island, NY 11964
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  Est $1,594,611

  Not Listed For Sale

  16 Great Circle Dr, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,637 Sq Ft
  • Built 1985

  16 Great Circle Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 390 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
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  /23

  $999,999

  $200K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft

  16 Bowditch Rd, Shelter Island, NY 11964

  Charming cottage-style home offering 3 bedrooms and 2 full baths in a highly desirable central location. Just moments from beautiful beaches, local restaurants, and boutique shops, this inviting property blends classic charm with modern updates. Renovated in 2019 with additional recent improvements, the home features comfortable living spaces filled with warmth and character. Outside, enjoy a

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  16 Bowditch Rd, Shelter Island, NY 11964
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  /45

  $12,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,604 Sq Ft
  • House for Rent

  4 Glynn Dr, Shelter Island, NY 11964

  This Shelter Island home is the kind of summer rental people wait all year to find-turnkey, stylish, and effortlessly comfortable. Recently renovated and designer-furnished, the home is ready for immediate enjoyment. Bright, sun-filled interiors and multiple inviting living spaces create an easy flow for summer living, whether it's slow mornings with coffee, afternoons by the pool, or relaxed

  Joseph Van Asco Douglas Elliman Real Estate

  4 Glynn Dr, Shelter Island, NY 11964
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  /46

  $3,025,000

  Sold Jul 14, 2026

  52 S Midway Rd, Shelter Island, NY 11964

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Built 1908

  Last Sold Summary

  • 19% Below List Price
  • $1,375/SF
  • 312 Days On Market

  Current Estimated Value $1,992,893

  Last Listing Agent Shane Donahue The Agency Hamptons

  52 S Midway Rd, Shelter Island, NY 11964
• 

  Est $2,399,513

  Not Listed For Sale

  3 Sea Gull Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft
  • Built 1953

  3 Sea Gull Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 322 Days On Market

  Last Listing Agent Cynthia Barrett Brown Harris Stevens Hamptons
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  /29

  $2,199,000

  • 5 Beds
  • 4 Baths
  • 2,642 Sq Ft

  64A N Midway Rd, Shelter Island, NY 11964

  A rare turnkey Shelter Island retreat with two distinct homes tucked away on nearly an acre in the heart of Shelter Island, 64A North Midway Road presents a truly unique opportunity to own two homes on one private property. Surrounded by mature trees, expansive lawns, and a picturesque pond next door, this exceptional estate blends privacy, flexibility, and timeless charm. This rare property

  Christine Beckwith Douglas Elliman Real Estate

  64A N Midway Rd, Shelter Island, NY 11964
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  /25

  $14,400 Per Month

  • 4 Beds
  • 2 Baths
  • 2,669 Sq Ft
  • Property for Rent

  12 Dogwood Ln, Shelter Island, NY 11964

  Discover the perfect island getaway in this spacious 4-bedroom, 2-bathroom home tucked away on a large, serene lot. Surrounded by mature landscaping, the property features a generous front porch overlooking a peaceful pond—an ideal spot for morning coffee or sunset relaxation. Inside, the home offers a bright and inviting layout with a well-appointed kitchen complete with a center island, perfect

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  12 Dogwood Ln, Shelter Island, NY 11964
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  /9

  $795,000

  Sold Oct 10, 2025

  33B S Midway Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2 Baths
  • Built 1950

  Last Sold Summary

  • 11% Below List Price
  • 142 Days On Market

  Current Estimated Value $788,183

  Last Listing Agent Shane Donahue The Agency Hamptons

  33B S Midway Rd, Shelter Island, NY 11964
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  Est $2,720,067

  Not Listed For Sale

  6 Behringer Ln, Shelter Island, NY 11964

  • 4 Beds
  • 3.5 Baths
  • 3,450 Sq Ft
  • Built 2023

  6 Behringer Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 263 Days On Market

  Last Listing Agent Sheri Winter Parker Corcoran
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  /16

  $1,595,000

  • Land
  • 27,007 Sq Ft
  • $2,572,581 per Acre

  9 Bay Shore Dr, Shelter Island, NY 11964

  Rare opportunity to own .62 Acres of waterfront buildable land along West Neck creek, offering a beautiful setting with water views and direct access to the shoreline. Nestled within the peaceful Silver Beach community, this private and tranquil property is surrounded by nature and offers an exceptional opportunity to create a waterfront retreat. Across the water, protected preserved land ensures

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  9 Bay Shore Dr, Shelter Island, NY 11964
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  /18

  $46,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,487 Sq Ft
  • House for Rent

  4 Ivy Place, Shelter Island, NY 11964

  $3,900 monthly (YEAR-ROUND RENTAL) Located in Hay Beach, this year round furnished rental is available and fully furnished. 3 bedrooms and 2 full baths is located in the beautiful area of Hay Beach, just 2 minutes from Gardiners Bay Country Club. Large living room with fireplace and sliders out to the large awning covered deck. Large loft area off the living room could serve as an office area of

  Sheri Winter Parker Corcoran

  4 Ivy Place, Shelter Island, NY 11964
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  $2,650,000

  Sold Oct 16, 2025

  7 Gazon Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,901 Sq Ft
  • Built 1955

  Last Sold Summary

  • 8% Below List Price
  • $1,394/SF
  • 130 Days On Market

  Current Estimated Value $2,903,665

  Last Listing Agent Terry Thompson Douglas Elliman Real Estate

  7 Gazon Rd, Shelter Island, NY 11964
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  Est $2,486,747

  Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Built 1954

  Unlisted Address

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Susan Cincotta Susan C Cincotta
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  /32

  $1,495,000

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft

  6 Oxford Ave, Shelter Island, NY 11964

  Rare opportunity to own a charming early-1900s Victorian farmhouse in the historic Heights. Set on a quiet road, this inviting home features an extra-large yard perfect for entertaining and a welcoming wraparound porch ideal for relaxing summer evenings. Inside, the home boasts a spacious living room with a wood-burning fireplace, a gracious parlor, formal dining room, and a first-floor bedroom

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  6 Oxford Ave, Shelter Island, NY 11964
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  /35

  $75,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,800 Sq Ft
  • House for Rent

  47L S Ferry Rd, Shelter Island, NY 11964

  Rental is Available in 2026: August $75,000. Located 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

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  47L S Ferry Rd, Shelter Island, NY 11964
• 

  $1,600,000

  Sold Aug 24, 2026

  73 N Midway Rd, Shelter Island, NY 11964

  • 4 Beds
  • 3 Baths
  • 2,296 Sq Ft
  • Built 1976

  Last Sold Summary

  • 16% Below List Price
  • $697/SF
  • 248 Days On Market

  Current Estimated Value $1,814,088

  Last Listing Agent JoAnn Wind Daniel Gale Sothebys Intl Rlty

  73 N Midway Rd, Shelter Island, NY 11964
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  Est $5,399,911

  Not Listed For Sale

  104 S Ferry Rd, Shelter Island, NY 11964

  • 5 Beds
  • 5.5 Baths
  • 4,040 Sq Ft
  • Built 2023

  104 S Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty
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  /25

  $6,995,000

  Pending

  • 6 Beds
  • 4 Baths

  33 Dinah Rock Rd, Shelter Island, NY 11964

  Nestled on approximately 2.1 acres with an impressive 186 feet of natural beachfront, 33 Dinah Rock Road is a rare west facing waterfront estate on Shelter Island. This elevated property, rising about 26 feet above sea level, delivers uninterrupted sunset views, refreshing southwest summer breezes, and sweeping vistas across the water. Its defining feature is the expansive private shoreline,

  Hedgerow Exclusive Team Hedgerow Exclusive Properties

  33 Dinah Rock Rd, Shelter Island, NY 11964
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  /23

  $8,700 Per Month

  • 4 Beds
  • 3 Baths
  • 2,018 Sq Ft
  • House for Rent

  59 Peconic Ave, Shelter Island, NY 11964

  Classic Cape Cod Retreat Near Shell BeachEnjoy summer on Shelter Island in this charming Cape Cod–style home with tranquil water views just across the street and easy access to one of the island’s most popular beaches. Located less than half a mile from Shell Beach, this 4-bedroom, 3-bath home is set in a friendly, sought-after summer community.The bright, open living and dining area

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  59 Peconic Ave, Shelter Island, NY 11964
• 

  $999,000

  Sold Jun 11, 2026

  10 Strawberry Ln, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1967

  Last Sold Summary

  • 23% Below List Price
  • $746/SF
  • 211 Days On Market

  Current Estimated Value $1,040,771

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  10 Strawberry Ln, Shelter Island, NY 11964
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  Est $2,225,052

  Not Listed For Sale

  8 Crescent Way, Shelter Island, NY 11964

  • 4 Beds
  • 3.5 Baths
  • 2,800 Sq Ft
  • Built 2017

  8 Crescent Way, Shelter Island, NY 11964

  Last Sold Summary

  • 96 Days On Market

  Last Listing Agent Christine Beckwith Douglas Elliman Real Estate
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  /3

  $575,000

  • Land
  • 25,264 Sq Ft
  • $991,379 per Acre

  21 Tims Trail, Shelter Island, NY 11964

  This quiet community known as Long View acres is the perfect place to build your Shelter Island dream home. Located just minutes from Bootleggers Alley Beach which is known for their spectacular sunsets. This .58-acre vacant lot backs up to historic Westmoreland Farms creating a beautiful backyard views.

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  21 Tims Trail, Shelter Island, NY 11964
• 

  $4,350,000

  Sold Oct 31, 2025

  7 Westmoreland Dr, Shelter Island, NY 11964

  • 6 Beds
  • 4.5 Baths
  • 4,957 Sq Ft
  • Built 1901

  Last Sold Summary

  • 1% Above List Price
  • $878/SF
  • 18 Days On Market

  Last Listing Agent Carl Gambino Compass Greater NY LLC

  7 Westmoreland Dr, Shelter Island, NY 11964
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  Est $1,791,667

  Not Listed For Sale

  79A N Midway Rd, Shelter Island, NY 11964

  • 4 Beds
  • 2.5 Baths
  • 1,794 Sq Ft
  • Built 1979

  79A N Midway Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 81 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
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  /30

  $2,800,000

  $150K PRICE DROP

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

  12 Terry Dr, Shelter Island, NY 11964

  Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach.Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  12 Terry Dr, Shelter Island, NY 11964
• 

  $5,700,000

  Sold Apr 07, 2026

  21 Thompson Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 2022

  Last Sold Summary

  • 16% Below List Price
  • $3,790/SF
  • 115 Days On Market

  Current Estimated Value $5,123,546

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  21 Thompson Rd, Shelter Island, NY 11964
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  Est $986,000

  Not Listed For Sale

  1 Rebel Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1981

  1 Rebel Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 174 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty
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  /44

  $4,995,000

  • 5 Beds
  • 6.5 Baths
  • 5,535 Sq Ft

  6 Great Circle Dr, Shelter Island, NY 11964

  Brand new in one of Shelter Island's premier enclaves along Gardiners Bay, this custom 5,535 +/- SF, south-facing residence developed by Juno Homes presents a refined blend of luxury, location, and design. Defined by soaring proportions, sleek attention to detail and bathed in natural light, the home features 5 ensuite bedrooms, 6 full baths and one half bathroom across two levels. Upon entry, a

  Kristy Naddell Douglas Elliman Real Estate

  6 Great Circle Dr, Shelter Island, NY 11964
• 

  $1,460,000

  Sold Aug 27, 2026

  26 S Menantic Rd, Shelter Island, NY 11964

  • 4 Beds
  • 3.5 Baths
  • 1,702 Sq Ft
  • Built 1960

  Last Sold Summary

  • 19% Below List Price
  • $858/SF
  • 305 Days On Market

  Current Estimated Value $1,542,850

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  26 S Menantic Rd, Shelter Island, NY 11964
• 

  Est $783,685

  Not Listed For Sale

  3 N Cartwright Rd, Shelter Island, NY 11964

  3 N Cartwright Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Scott Bennett Douglas Elliman Real Estate
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  /12

  $3,499,000

  • 4 Beds
  • 3.5 Baths
  • 3,856 Sq Ft

  9 Locust Woods Dr, Shelter Island, NY 11964

  Welcome to Shelter Island — a place where time slows down and nature takes center stage.Accessible only by ferry, this rare island community offers a level of peace, privacy, and authenticity that is nearly impossible to find in today’s world. Set on over 2 acres of beautifully engineered rolling landscape, this property has been thoughtfully designed to enhance natural beauty while

  Ron Moschetta Keller Williams Realty Greater

  9 Locust Woods Dr, Shelter Island, NY 11964
• 

  $660,000

  Sold Dec 02, 2025

  8 Wheeler Rd, Shelter Island, NY 11964

  • Land
  • 1.2 Acres
  • $550,000 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 99 Days On Market

  Last Listing Agent Nicholas Planamento William Raveis New York LLC

  8 Wheeler Rd, Shelter Island, NY 11964
• 

  Est $1,612,958

  Not Listed For Sale

  1 Deer Park Ln, Shelter Island, NY 11964

  • 3 Beds
  • 3.5 Baths
  • 2,460 Sq Ft
  • Built 1993

  1 Deer Park Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 153 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

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