Shelter Island Heights, NY Homes

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  $5,500,000

  • 4 Beds
  • 5.5 Baths
  • 4,000 Sq Ft

  11 Sunnyside Ave, Shelter Island Heights, NY 11965

  An architecturally significant modern retreat set on two private acres within coveted Shelter Island Heights owners association. Floor-to-ceiling glass dissolves the boundary between indoors and out, framing the surrounding natural environment from nearly every room. Conceived by developer Angelo Varischetti in collaboration with the award-winning team at WE+ Architecture & Design, the home is a

  

  Benjamin Dixon

  Douglas Elliman Real Estate

  11 Sunnyside Ave, 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
• 

  $1,999,999

  Sold Jun 24, 2026

  5 Grand Ave, Shelter Island Heights, NY 11965

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2024

  Last Sold Summary

  • 33% Below List Price
  • $1,000/SF
  • 104 Days On Market

  Current Estimated Value $1,358,228

  Last Listing Agent Hedgerow Exclusive Team Hedgerow Exclusive Properties

  5 Grand Ave, Shelter Island Heights, NY 11965
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  Est $1,941,038

  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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  /35

  $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
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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 $1,659,157

  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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  $1,035,000

  $50K PRICE DROP Pending

  • 3 Beds
  • 2 Baths

  26 Ole Buck Run, Shelter Island, NY 11964

  ***NEW PRICE*** This recently renovated 3 bedroom, 2 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 and painted interior. New back decks and exterior basement entry. Full basement with a walkout makes for a possible fourth ensuite bedroom. Adjacent to the 14 acre Westmoreland Farm Open

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  26 Ole Buck Run, Shelter Island, NY 11964
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  $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
• 

  $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 $2,754,787

  Last Listing Agent Terry Thompson Douglas Elliman Real Estate

  7 Gazon Rd, Shelter Island, NY 11964
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  Est $2,807,080

  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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  $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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  /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
• 

  $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 $3,643,791

  Not Listed For Sale

  5 Bay Shore Dr, Shelter Island Heights, NY 11965

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 1954

  5 Bay Shore Dr, Shelter Island Heights, NY 11965

  Last Sold Summary

  • 233 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
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  $995,000

  $100K PRICE DROP

  • Land
  • 27,878 Sq Ft
  • $1,554,688 per Acre

  12 Hilo Dr, Shelter Island, NY 11964

  .64 Acres on Shelter Island, adjacent to cumminty dock. Room fof house and pool

  Brian Buckhout Compass

  12 Hilo Dr, Shelter Island, NY 11964
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  $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
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  Est $2,206,527

  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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  /25

  $6,995,000

  • 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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  $1,180,000

  Sold Mar 26, 2026

  1 Gazon Rd, Shelter Island, NY 11964

  • 4 Beds
  • 3 Baths
  • 2,618 Sq Ft
  • Built 1962

  Last Sold Summary

  • 13% Below List Price
  • $451/SF
  • 151 Days On Market

  Current Estimated Value $1,467,337

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  1 Gazon Rd, Shelter Island, NY 11964
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  Est $1,008,000

  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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  $2,950,000

  • 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
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  $1,725,000

  Sold Jan 14, 2026

  27 Country Club Dr, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 3,170 Sq Ft
  • Built 2011

  Last Sold Summary

  • 13% Below List Price
  • $544/SF
  • 221 Days On Market

  Current Estimated Value $2,259,209

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  27 Country Club Dr, Shelter Island, NY 11964
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  Est $1,288,939

  Not Listed For Sale

  36 Rocky Point Rd, East Marion, NY 11939

  • 2 Beds
  • 1.5 Baths
  • 1,411 Sq Ft
  • Built 1992

  36 Rocky Point Rd, East Marion, NY 11939

  Last Sold Summary

  • 100 Days On Market

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

  Last Sold Summary

  • 111 Days On Market

  Last Listing Agent Annmarie Seddio Atlas Sales Realty
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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 addressing

  Ron Moschetta Keller Williams Realty Greater

  9 Locust Woods Dr, Shelter Island, NY 11964
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  Est $1,695,408

  Not Listed For Sale

  5 Country Club Dr, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft
  • Built 1986

  5 Country Club Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 304 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
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  /26

  $2,700,000

  • 6 Beds
  • 3 Baths
  • 5,900 Sq Ft

  2 Prospect Ave, Shelter Island, NY 11964

  A rare opportunity to own a legacy compound on Shelter Island, this offering brings together three income-producing historic cottages and a separate buildable lot, all just moments from the water. Positioned at 2 Prospect Avenue and 38 Rock Point Road, the properties are offered as one cohesive investment, blending immediate revenue with exceptional future potential. Each of the three cottages

  Marco Maida Compass Greater NY LLC

  2 Prospect Ave, Shelter Island, NY 11964
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  Not Listed For Sale

  31 Terry Dr, Sag Harbor, NY 11963

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Built 1971

  31 Terry Dr, Sag Harbor, NY 11963

  Last Sold Summary

  • 108 Days On Market

  Last Listing Agent Kelly DiJorio Daniel Gale Sothebys Intl Rlty
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  /28

  $3,850,000

  New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,985 Sq Ft

  8 Hilo Dr, Shelter Island, NY 11964

  This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail,

  Enzo Morabito Douglas Elliman Real Estate

  8 Hilo Dr, Shelter Island, NY 11964
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  Est $2,137,405

  Not Listed For Sale

  74 Peconic Ave, Shelter Island, NY 11964

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1953

  74 Peconic Ave, Shelter Island, NY 11964

  Last Sold Summary

  • 73 Days On Market

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

  $2,595,000

  • 4 Beds
  • 2.5 Baths
  • 1,994 Sq Ft

  11 Prospect Ave, Shelter Island, NY 11964

  Shelter Island Heights IconGracefully positioned in the heart of Shelter Island Heights, this timeless residence has been thoughtfully renovated and restored to honor its original character while seamlessly incorporating today's modern comforts. Rich in architectural charm and classic detail, the home offers an elegant blend of historic beauty and refined living. A gracious, oversized covered

  Donna Walker Douglas Elliman Real Estate

  11 Prospect Ave, Shelter Island, NY 11964
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  Est $3,736,000

  Not Listed For Sale

  148E N Ferry Rd, Shelter Island, NY 11964

  • 3 Beds
  • 3 Baths
  • 2,350 Sq Ft
  • Built 1990

  148E N Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 79 Days On Market

  Last Listing Agent Bridget Elkin Compass Greater NY LLC
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  /18

  $4,000,000

  • 3 Beds
  • 3 Baths

  100 Peconic Ave, Shelter Island, NY 11964

  This waterfront is classic Shelter Island. Set on more than half an acre with 153 feet of private, bulkheaded sandy beach, this 1952 cottage keeps its head turned to the water from nearly every room. A fireplace and hardwood floors anchor the living room, the primary suite wakes to the Bay, and a covered waterside patio waits for the long part of the evening. Wooden steps lead down to your own

  Melina Wein Compass

  100 Peconic Ave, Shelter Island, NY 11964
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  Est $1,812,000

  Not Listed For Sale

  10 Penny's Path, Shelter Island, NY 11964

  • 4 Beds
  • 3 Baths
  • 2,270 Sq Ft
  • Built 1980

  10 Penny's Path, Shelter Island, NY 11964

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty
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  $4,250,000

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

  169 N Ferry Rd, Shelter Island, NY 11964

  There are new homes, and then there is this - a turnkey Bartilucci Construction design-build masterpiece, styled by Heiberg Cummings tucked just outside the heart of Shelter Island Heights. No detail left to chance and no corner cut. What sets this location apart is the rare balance it strikes - total privacy paired with true convenience. The Heights business district, morning coffee, boutique

  Sheri Winter Parker Corcoran

  169 N Ferry Rd, Shelter Island, NY 11964
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  Est $1,230,506

  Not Listed For Sale

  1 Worthy Way, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 1,217 Sq Ft
  • Built 1980

  1 Worthy Way, Shelter Island, NY 11964

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty
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  /29

  $1,500,000

  Pending

  • 5 Beds
  • 2.5 Baths
  • 2,845 Sq Ft

  5 Spring Garden Ave, Shelter Island, NY 11964

  Steeped in history and timeless architectural charm, this rare circa-1872 Gothic Revival cottage is located within the historic district of Shelter Island Heights, listed on both the National and New York State Registers of Historic Places. Beautifully preserved and largely unchanged since its original design, the home is a remarkable example of the picturesque residential style created by

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  5 Spring Garden Ave, Shelter Island, NY 11964

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