10

Shelter Island, NY Homes for Sale with Acreage

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  • /41

    $2,999,000

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

    13 Tarkettle Rd, Shelter Island, NY 11964

    Nestled on a 1.08 acre lot along Shelter Island’s coveted Dickerson Creek, this Scandinavian-style waterfront cottage embodies quintessential Hamptons elegance with 100 feet of picturesque shoreline and a sparkling pool.Inside, a light-filled and inviting floor plan features three bedrooms and two newly updated bathrooms, designed for modern comfort. The stylishly renovated kitchen is sure to

    Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

    13 Tarkettle Rd, Shelter Island, NY 11964
  • /2

    $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
  • /27

    $2,350,000

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

    23 Osprey Rd, Shelter Island, NY 11964

    Situated in the desirable Sherwood 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
  • /15

    $3,850,000

    • 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
  • /28

    $4,445,000

    • 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
  • /7

    $695,000

    • Land
    • 1 Acre
    • $695,000 per Acre

    1 Strawberry Ln, Shelter Island, NY 11964

    This truly magical building lot is ready for your dream home. A full acre of land with test well in place. "C" Zone which is the least restrictive residential zone on Shelter Island. A stone's throw from Fresh Pond and short distance to Wades Beach. Quiet location. Close to shops, school, library, restaurants and beaches. Exclusive: $695K

    Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

    1 Strawberry Ln, Shelter Island, NY 11964
  • /23

    $499,000

    • 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 and dryer 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
  • /46

    $1,695,000

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

    26 S Menantic Rd, Shelter Island, NY 11964

    Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the

    Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

    26 S Menantic Rd, Shelter Island, NY 11964
  • /18

    $6,999,000

    • Land
    • 6 Acres
    • $1,166,500 per Acre

    3a/3b Pandion Rd Unit 3a/3b, Shelter Island, NY 11964

    In a market where exceptional land opportunities are scarce, this rare property on Shelter Island presents the chance to create your ultimate Hamptons waterfront compound. With 875 feet of water frontage, this six-acre, two-parcel offering along Coecles Harbor comes with architectural plans fully approved by both the Suffolk County Department of Health Services and the Department of Environmental

    Matthew Breitenbach Compass

    3a/3b Pandion Rd Unit 3a/3b, Shelter Island, NY 11964
  • /47

    $4,250,000

    • 4 Beds
    • 7 Baths
    • 5,500 Sq Ft

    141A N Ferry Rd, Sag Harbor, NY 11963

    Welcome to this exceptional custom-built home nestled on 1.1 secluded acres, offering the perfect blend of luxury, comfort and privacy. Hidden at the end of a long driveway, the main house boasts 3 bedrooms and 3.5 bathrooms. The 1st floor main suite features include double doors that open to a private deck, a WIC and an expansive master bathroom equipped with a spa style rain shower. To add to

    Annmarie Seddio Atlas Sales Realty

    141A N Ferry Rd, Sag Harbor, NY 11963

Home Trends in Shelter Island, NY

Housing Trends

Median Sale Price
$2,650,000
Median Single Family Sale Price
$2,664,500
Median 1 Bedroom Sale Price
$499,000
Average Price Per Sq Ft
$932
Number of Homes for Sale
17
Last 12 months Home Sales
11
Months of Supply
18.50
Median List Price
$2,490,000
Median Change From 1st List Price
11%
Median Home Sale Price YoY Change
34%
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