2,271

Shelter Island, NY Homes

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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

    Agent Photo

    Elizabeth Melichar

    Serhant East End LLC

    (631) 892-2854

    90 Peconic Ave, Shelter Island, NY 11964
  • /13

    $12,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • House for Rent

    6 Community Dr, Shelter Island, NY 11964

    Property Id: 2533314Beautifully renovated and refurnished 3 bedroom 1 bath home with central air, washer/dryer & outdoor shower within a stone's throw to West Neck Bay and community dock. Perfect spot for entertaining on warm summer nights with a spacious yard, deck, fire pit, grill & outdoor furniture.Available July $12,000; August $13,000; Aug-LD $14,000; Extended Season

    (631) 994-1841

    6 Community Dr, Shelter Island, NY 11964
  • 156 Ram Island Dr, 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 $2,911,090

    Last Listing Agent Mary Elizabeth Galle Corcoran

    156 Ram Island Dr, Shelter Island, NY 11964
  • /20

    $2,675,000

    Pending
    • 4 Beds
    • 3 Baths

    55 Peconic Ave, Shelter Island, NY 11964

    Welcome to 55 Peconic Avenue, a bold, newly built statement home completed in 2022 and set on an expansive 1.4-acre parcel in one of Shelter Island's most coveted locations. Designed for true year-round living, this residence captures southwest-facing water views, dramatic light, and a seamless indoor-outdoor lifestyle that today's buyers demand. The main level delivers a clean, open-concept

    Jack Richardson SERHANT.

    55 Peconic Ave, Shelter Island, NY 11964
  • /14

    $15,000 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    24 Worthy Way, Shelter Island, NY 11964

    Property Id: 2474336Perfect summer rental. A 3BR, 2BA Ranch that has been recently renovated. Large backyard deck for outside dining, close to beaches. EV Level 2 charging outlet. Available July $15,000; August $16,000.

    (631) 449-7983

    24 Worthy Way, Shelter Island, NY 11964
  • 33B S Midway Rd, Shelter Island, NY 11964

    $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 $714,992

    Last Listing Agent Shane Donahue The Agency Hamptons

    33B S Midway Rd, Shelter Island, NY 11964
  • /30

    $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
  • /11

    $10,000 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    6 Crab Creek Rd, Shelter Island, NY 11964

    Property Id: 2474324Many updates with great rental rates. Open floor plan, beautiful sunlit enclosed porch, entertaining deck overlooking quiet grassy yard, and outdoor shower to rinse off from coming from the sandy beach close by. There are 3BR, master with brand new bathroom, and an additional full bathroom, and finished basement. June $7,000; July $10,000; June-July $15,000. Short term

    (631) 459-4426

    6 Crab Creek Rd, Shelter Island, NY 11964
  • 7 Gazon Rd, 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 $2,796,014

    Last Listing Agent Terry Thompson Douglas Elliman Real Estate

    7 Gazon Rd, Shelter Island, NY 11964
  • /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
  • /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
  • 7 Westmoreland Dr, 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
  • /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
  • /22

    $25,000 Per Month

    • 4 Beds
    • 3 Baths
    • House for Rent

    70 S Ferry Rd, Shelter Island, NY 11964

    Beautifully renovated and furnished and now ready for its first tenants. This lovely two story home is your perfect retreat. A wonderful location close to Wades Beach, The South Ferry, and the 2,350 acre Mashomack Park and Preserve. The house sits on a 1.13 landscaped acre property complete with a heated gunite pool, pool house, outdoor shower, and spacious entertainment patio. The tranquil

    70 S Ferry Rd, Shelter Island, NY 11964
  • 21 Thompson Rd, 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 $5,504,973

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

    21 Thompson Rd, Shelter Island, NY 11964
    • Unlisted Address

      Est $2,310,422

      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

  • /15

    $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
  • /26

    $7,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    42 N Menantic Rd, Shelter Island, NY 11964

    Escape to Tranquility Base, a light-filled modern retreat where timeless mid-century style meets today's elevated comforts. Thoughtfully renovated and expanded, this 4-bedroom, 2.5-bath home is surrounded by lush, landscaped grounds and designed for seamless indoor-outdoor living-thanks to five sliding glass doors that open to a heated gunite pool and expansive entertaining deck. Enjoy the

    Jeanmarie Bay William Raveis (Greenport)

    42 N Menantic Rd, Shelter Island, NY 11964
  • 8 Wheeler Rd, 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
  • /46

    $3,150,000

    $600K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft

    52 S Midway Rd, Shelter Island, NY 11964

    Around the bend from Turkem's Rest and a short paddle from Salt and Shipwreck, this recently renovated, 4-bedroom, circa 1908 Shelter Island farmhouse, on a shy acre, is perched above Menantic Creek with a substantial dock and profits from panoramic water views with southwestern exposure for magical sunsets. Wide waterfront vistas unfold across beautiful landscaping by Marders, broad greens lined

    Shane Donahue The Agency Hamptons

    52 S Midway Rd, Shelter Island, NY 11964
  • /41

    $32,500 Per Month

    • 4 Beds
    • 3 Baths
    • House for Rent

    22 St Mary's Rd, Shelter Island, NY 11964

    Stunning new modern home with an abundance of natural light throughout. 4 bedroom, 3 bath home with plenty of room for your loved ones. Home has a large open living space with oak floors and high ceilings with huge Anderson doors that opens onto extensive covered deck for seamless indoor outdoor entertaining. Two guest bedrooms and a bathroom complete the first floor. The master suite is on the

    22 St Mary's Rd, Shelter Island, NY 11964
  • 1 Gazon Rd, Shelter Island, NY 11964

    $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 $1,293,948

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    1 Gazon Rd, Shelter Island, NY 11964
  • /28

    $4,445,000

    New Construction $450K 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
  • /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
  • 27 Country Club Dr, 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 $2,311,551

    Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

    27 Country Club Dr, Shelter Island, NY 11964
  • /29

    $2,495,000

    • 4 Beds
    • 3 Baths

    100 S Midway Rd, Shelter Island, NY 11964

    A stone's throw from popular Wades Beach this spacious contemporary is situated on an acre of park like grounds. Four bedrooms, three baths. Living room with vaulted ceilings and wood burning fireplace. Chef's kitchen with open floor plan. Lower level walkout with library/family room and wet bar. Large decks overlooking a heated gunite swimming pool with park like grounds. Exclusive: $2.495M

    Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

    100 S Midway Rd, Shelter Island, NY 11964
  • /25

    $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
  • /8

    $2,350,000

    • 4 Beds
    • 3.5 Baths
    • 2,777 Sq Ft

    5 Marc St, Shelter Island, NY 11964

    Welcome to your dream getaway where modern luxury meets laid-back coastal charm. This Newly renovated 4 Bedroom 3.5 Bathroom home offers perfect blend of style & tranquility, just moments from beaches, marinas and all that island has to offer. Designer Kitchen with Quartz countertops. custom soft close cabinetry with center island & high end appliances. Located on first floor Primary Bedroom with

    Anthony Guidice RE/MAX Signature Real Estate

    5 Marc St, Shelter Island, NY 11964
  • /26

    $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
  • /30

    $2,485,000

    • 6 Beds
    • 4 Baths
    • 3,413 Sq Ft

    14 Freds Ln, Shelter Island, NY 11964

    Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with

    Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

    14 Freds Ln, Shelter Island, NY 11964
  • /18

    $54,000 Per Month

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

    4 Ivy Place, Shelter Island, NY 11964

    $4,500 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

Showing Results 1 - 40, Page 1 of 18

Home Trends in Shelter Island, NY

Housing Trends

Median Sale Price
$2,664,500
Median Single Family Sale Price
$2,695,000
Median 1 Bedroom Sale Price
$499,000
Average Price Per Sq Ft
$903
Number of Homes for Sale
22
Last 12 months Home Sales
8
Months of Supply
33.00
Median List Price
$2,695,000
Median Change From 1st List Price
12%
Median Home Sale Price YoY Change
37%
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