Shelter Island, NY Homes

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  /27

  $1,895,000

  $455K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,484 Sq Ft

  23 Osprey Rd, Shelter Island, NY 11964

  Situated in the desirable Shorewood Farms neighborhood, just moments from the private beach and tennis court, this charming shingled home has been fully refreshed and is move in ready. Built in 2005 by renowned Shelter Island builder, George Phriender, it is convenient to the South Ferry as well as south shore restaurants and marinas. Enjoy the peace and quiet of Shelter Island only a few minutes

  Kieran Brew SERHANT.

  23 Osprey 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 $1,415,698

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  1 Gazon Rd, Shelter Island, NY 11964
• 

  Not Listed For Sale

  18 Dickerson Dr, Shelter Island, NY 11786

  • 4 Beds
  • 3.5 Baths
  • 2,774 Sq Ft
  • Built 1973

  18 Dickerson Dr, Shelter Island, NY 11786

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Michael Brennan Douglas Elliman Real Estate
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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
• 

  $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 $2,090,595

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  27 Country Club Dr, Shelter Island, NY 11964
• 

  Est $1,725,438

  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
• 

  

  /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
• 

  Est $2,731,570

  Not Listed For Sale

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

  • 3 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1985

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

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Michael Brennan Douglas Elliman Real Estate
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  /7

  $6,395,000

  • 5 Beds
  • 6.5 Baths
  • 4,250 Sq Ft

  8 Margaret's Dr, Shelter Island, NY 11964

  Set on 1.05± acres along the shores of West Neck Creek, 8 Margaret's Drive presents a newly constructed waterfront residence designed to embrace the natural beauty and relaxed character of Shelter Island. With direct frontage along the creek and a thoughtful orientation toward the water, the property brings together refined new construction, generous outdoor living, and a private waterfront

  Hedgerow Exclusive Team Hedgerow Exclusive Properties

  8 Margaret's Dr, Shelter Island, NY 11964
• 

  Est $2,116,240

  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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  /49

  $2,995,000

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  13 Spring Garden Ave, Shelter Island Heights, NY 11965

  Own a distinctive piece of Shelter Island Heights history in this beautifully restored circa-1875 residence, thoughtfully updated for today’s lifestyle while retaining the character and architectural details that make a historic home so special. Set on approximately 0.40 acres, the property offers second-level water views, inviting private gardens, and a classic wraparound porch ideal for

  Douglas Cabral Century 21 Excelsior Realty

  13 Spring Garden Ave, Shelter Island Heights, NY 11965
• 

  Est $3,741,000

  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
• 

  

  /25

  $2,200,000

  $395K PRICE DROP

  • 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
• 

  Est $2,020,680

  Not Listed For Sale

  6 Evans Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 1986

  6 Evans Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 267 Days On Market

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
• 

  

  /30

  $8,900,000

  • 6 Beds
  • 9 Baths
  • 7,300 Sq Ft

  22 Locust Point Rd, Shelter Island, NY 11964

  Rarely available in an enviable location directly across from the water with mooring rights, this new construction home in Dering Harbor delivers the best of Hamptons living on Shelter Island, ready for immediate enjoyment and for generations to come. Built in 2026 and sited on 2.4 acres, the new construction property has 7,300 +/- SF of interior living space (including the finished lower level)

  Romaine Gordon Saunders & Associates

  22 Locust Point Rd, Shelter Island, NY 11964
• 

  Est $1,887,829

  Not Listed For Sale

  2 Dering Woods Rd, Shelter Island, NY 11964

  2 Dering Woods Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 373 Days On Market

  Last Listing Agent Annmarie Seddio Atlas Sales Realty
• 

  

  /35

  $2,349,000

  • 3 Beds
  • 2.5 Baths
  • 3,312 Sq Ft

  5 + Part 3 Hagar Rd, Shelter Island, NY 11964

  Set on 1.06 acres with elevated sunrise vistas, this freshly renovated single-story cottage is fully turn-key. The entry foyer, featuring a powder room and separate laundry room, opens to a bright, vaulted main living space that seamlessly combines living and dining areas, featuring a wood-burning fireplace with raised hearth. Strategically placed windows, including a striking round accent window

  Penelope Moore SAUNDERS & ASSOCIATES

  5 + Part 3 Hagar Rd, Shelter Island, NY 11964
• 

  Est $978,448

  Not Listed For Sale

  29 St Marys Rd, Shelter Island, NY 11964

  • Built 1955

  29 St Marys Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 215 Days On Market

  Last Listing Agent Richard Connelly Douglas Elliman Real Estate
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  /45

  $1,850,000

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  4 Irene Ln, Sag Harbor, NY 11963

  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

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  4 Irene Ln, Sag Harbor, NY 11963
• 

  Est $1,717,617

  Not Listed For Sale

  5 Wade Rd, Shelter Island, NY 11964

  • 3 Beds
  • 3 Baths
  • 1,854 Sq Ft
  • Built 1967

  5 Wade Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Rosanna Piazza Signature Premier Properties
• 

  

  /28

  $4,295,000

  New Construction $600K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 5,622 Sq Ft

  100 S Ferry Rd, Shelter Island, NY 11964

  A buyers dream rooted in nature, enhanced by design. This modern farmhouse nestled in the heart of Shelter Island, NY. completed in 2024, sits on a generous 2.16 acres of immaculate grounds, is a mere half mile from the South Ferry, placing convenience at your doorstep.Boasting six bedrooms, each with their own en-suite, and two additional half-baths, this residence effortlessly blends style

  Christine Beckwith Douglas Elliman Real Estate

  100 S Ferry Rd, Shelter Island, NY 11964
• 

  Est $1,720,562

  Not Listed For Sale

  7 Marc St, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1966

  7 Marc St, Shelter Island, NY 11964

  Last Sold Summary

  • 103 Days On Market

  Last Listing Agent Rachel Rushforth-Worrell Sothebys Int'l Realty Hamptons
• 

  

  /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
• 

  Est $899,143

  Not Listed For Sale

  68 S Ferry Rd, Shelter Island, NY 11964

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1960

  68 S Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 287 Days On Market

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

  

  /41

  $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
• 

  Est $1,598,447

  Not Listed For Sale

  63 N Midway Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 2,150 Sq Ft
  • Built 1920

  63 N Midway Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Linda Mccarthy Daniel Gale Sothebys Intl Rlty
• 

  

  /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
• 

  Est $1,504,839

  Not Listed For Sale

  5 Emerson Ln, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft
  • Built 2016

  5 Emerson Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Dawn Watson Serhant East End LLC
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  /29

  $2,245,000

  $250K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft

  100 S Midway Rd, Shelter Island, NY 11964

  Just a stone's throw from popular Wades Beach, this spacious contemporary sits on a beautifully landscaped acre of park-like grounds. The home features four bedrooms and three baths, along with a light-filled living room with vaulted ceilings and a wood-burning fireplace. The chef's kitchen opens seamlessly to the living and dining areas, creating an ideal open-concept floor plan. The lower-level

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  100 S Midway Rd, Shelter Island, NY 11964
• 

  Est $5,078,611

  Not Listed For Sale

  6 Club Dr, Shelter Island, NY 11964

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft
  • Built 1973

  6 Club Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Edward Mulderrig Compass Greater NY LLC
• 

  

  /29

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  4 Duvall Rd, Shelter Island, NY 11964

  Amazing 1800s house with 3 bedrooms and 2 baths. Perfectly quiet location in Shelter Island! Tennis courts directly across the street and backyard view of rolling land, minutes to the beach and a few steps to restaurants and gallery.

  Simon Harrison Simon Harrison Real Estate

  4 Duvall Rd, Shelter Island, NY 11964
• 

  Est $1,308,729

  Not Listed For Sale

  105 S Ferry Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2.5 Baths
  • 1,726 Sq Ft
  • Built 1977

  105 S Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 177 Days On Market

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

  

  /21

  $499,000

  Pending

  • 1 Bed
  • 1 Bath
  • 39,964 Sq Ft

  13 Winthrop Rd Unit 24, Shelter Island, NY 11964

  Discover effortless living in this beautifully renovated one-bedroom, one bath co-op on Shelter Island. The apartment is set within a serene and private eight-acre community. Thoughtfully updated, the residence features a modern kitchen and bath, with Bosch appliances, including an in-unit washer anddryer for ultimate convenience. The home opens to a private deck-perfectly suited for outdoor

  Elizabeth Wohl Brown Harris Stevens Hamptons

  13 Winthrop Rd Unit 24, Shelter Island, NY 11964
• 

  Est $1,761,000

  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
• 

  

  /32

  $2,690,000

  • 4 Beds
  • 2.5 Baths
  • 2,289 Sq Ft

  7 Wheeler Rd, Shelter Island, NY 11964

  Shelter Island Waterfront with Dock. A rare opportunity to own waterfront in Silver Beach, one of Shelter Island’s most beautiful and sought-after enclaves. Set directly on the tranquil Silver Beach lagoon, this four-bedroom, 2.5-bath home offers approximately 2,289 square feet on a private .76-acre property with approximately 102 feet of waterfront frontage—all just a five-minute walk to

  Matthew Hart World Prop Intl Sea to Sky

  7 Wheeler Rd, Shelter Island, NY 11964
• 

  Est $1,222,702

  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
• 

  

  /39

  $1,685,000

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  6 Cozy Ln, Shelter Island, NY 11964

  A perfect blend of stylish comfort and effortless one-level living, this traditional ranch-style home is a short walk to Silver Beach. Nestled on a quiet street surrounded by a beautifully wooded property with seasonal variety landscaping, this residence offers a private sanctuary designed for year-round relaxation and entertainment. The interior spaces extend beautifully to the outdoors,

  John Catrambone DERING HARBOR REAL ESTATE LLC

  6 Cozy Ln, Shelter Island, NY 11964
• 

  Est $1,437,068

  Not Listed For Sale

  27 Terry Dr, Shelter Island, NY 11964

  • 4 Beds
  • 3 Baths
  • 2,098 Sq Ft
  • Built 1974

  27 Terry Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 186 Days On Market

  Last Listing Agent Annmarie Seddio Atlas Sales Realty
• 

  

  /35

  $3,795,000

  • 5 Beds
  • 5 Baths
  • 3,072 Sq Ft

  5 Sea Gull Rd, Shelter Island, NY 11964

  Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtaking views across Mabel’s Creek and the South Fork, with a sandy beach just steps from your door. As a resident of Shorewood Farms, you’ll also enjoy exclusive access to a private association beach and tennis courts, enhancing the

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  5 Sea Gull Rd, Shelter Island, NY 11964
• 

  Est $1,458,148

  Not Listed For Sale

  1 Behringer Ln, Shelter Island, NY 11964

  • 4 Beds
  • 2.5 Baths
  • 1,860 Sq Ft
  • Built 1977

  1 Behringer Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Christopher Griffing Atlas Sales Realty

Showing Results 41 - 80, Page 2 of 18