SHELTER ISLAND, NY
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Homes For Sale in Shelter Island, NY

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Shelter Island

Nestled between the North and South Forks of Long Island, Shelter Island is a unique community that seamlessly combines quirky, artsy, rural and cosmopolitan; it is a place where cultures relax, work and play together, from the farm stands to the country club. The Island boasts many restaurants offering the freshest seafood and a variety of cuisines. Islanders (both visitors and residents) enjoy boating, golfing, fishing, and hiking. There are over 70 boat landings open for residents.

Shelter Island & Shelter Island Heights

Total Listings: 33
Average Price: $1,750,258
Highest Price: $6,900,000
Lowest Price: $395,000

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Daniel Gale Sotheby's Open Houses

$4,950,000

23 Freds Ln 5 Beds, 7.00 Baths, 1.10 Acres
Open House Date/Time Sat Nov 25 2017 (1:30 PM to 3:00 PM)

$4,700,000

1 Dering Woods Ln 5 Beds, 6.00 Baths, 3.25 Acres
Open House Date/Time Sat Nov 25 2017 (11:30 AM to 1:00 PM)

$1,295,000

18 Sunshine Rd 4 Beds, 3.00 Baths, 0.91 Acres
Open House Date/Time Sat Nov 25 2017 (1:00 PM to 3:00 PM)

$995,000

149 N Ferry Rd 3 Beds, 3.00 Baths, 0.87 Acres
Open House Date/Time Fri Nov 24 2017 (11:00 AM to 12:30 PM)

$945,000

44 Country Club Dr 4 Beds, 3.00 Baths, 1.00 Acres
Open House Date/Time Fri Nov 24 2017 (1:00 PM to 2:00 PM)

Shelter Island Homes For Sale

31 Properties Found. Page 1 of 1
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$5000.00 Selling Bonus If In Contract Before Ja...

$1,299,000

13 Locust Woods Dr, Shelter Island

  • 6 Beds
  • 5 Baths
  • 2.1 Acres
  • 4,128 sqft

School District: Shelter Island

$5000.00 Selling Bonus If In Contract Before Jan 1,2018. Gorgeous 4200 Sq Ft. Home. Must See. Including Pool, Fireplaces, 3 Car Garage, Beautiful Mahogany Wrap Around Porch And Decking, Located At End Of A Cul-de- Sac, Quiet And Peaceful Street. A Magnific...

As You Approach Ram Island The Feeling Of Priva...

$2,999,000

139 Ram Island Dr, Shelter Island

  • 4 Beds
  • 3 Baths
  • 2.4 Acres
  • 2,150 sqft

School District: Shelter Island

As You Approach Ram Island The Feeling Of Privacy And Prestige Is Clear. The 2 Acre Properties Eye Opening Hill Top Entry And Bay Views Instantly Catch Your Eye. From The Top Of The Drive To Lovely Contentemory Down By The Bay Front, This Bulk Headed Waterf...

This Well Thought Out Property Is Designed For ...

$1,950,000

13 Brander Pky, Shelter Island

  • 5 Beds
  • 6 Baths
  • 1.45 Acres
  • 3,868 sqft

School District: Shelter Island

This Well Thought Out Property Is Designed For A 3,868 Square Feet Home With 2 Master Suites And 3 Additional Bedrooms With Bathrooms, The Kitchen Is Suited For Any Cook. The Garage Has A Living Space Above For Additional Guests. Also A Pool House And A 20x...

Simply Stunning New Construction W/water Views ...

$3,375,000

6 J Hagar Rd, Shelter Island

  • 4 Beds
  • 3 Baths
  • 1 Acres

School District: Shelter Island

Simply Stunning New Construction W/water Views From Every Room. An Incredible Setting W/589 Feet Of Waterfront, Dock & Gunite, 18x36, Heated Pool. Living Rm W/fireplace Opens To Elevated Deck. Eat In Kitchen & Formal Dining Area Open To Dining Deck. Wander ...

Saltbox Modern In South Ferry Hills With Associ...

REDUCED 3%

$774,000

105 S Ferry Rd, Shelter Island

  • 2 Beds
  • 3 Baths
  • 0.87 Acres
  • 1,726 sqft

School District: Shelter Island

Saltbox Modern In South Ferry Hills With Association Beach And Boating. This Custom Board And Batten 2 Story With Loft And Redwood Plank Soaring Ceiling Is Open, Airy And Full Of Light. The Sun Room Enclosed Porch Is Used In Most Seasons. Vermont Castings W...

Enjoy The Tranquility Of Shelter Island. This 9...

$6,900,000

29 Winthrop Rd, Shelter Island

  • 6 Beds
  • 10 Baths
  • 1.71 Acres

School District: Shelter Island

Enjoy The Tranquility Of Shelter Island. This 9,230 Sq. Ft. Home Located On 1.7 Acres Was Rebuilt In 2010. Features Include Scenic Views Of Dering Harbor, 600 Ft Of Private Beach, A 168 Ft Deep Water Dock, A Deeded Mooring, Five Fireplaces, A Four-car Garag...

Stoneleigh Subdivision, Comprised Of Four Lots ...

Photo of Listing #2942695

$1,599,000

56-60 N Menantic Rd, Shelter Island

  • 4.7 Acres

School District: Shelter Island

Stoneleigh Subdivision, Comprised Of Four Lots Approved/filed Subdivision Totaling 4.7 Acres. Roads, Utilities, Storm Water Drainage & 10,000 Gallon Fire Cistern In Place. Addresses: 56a, 56b, 58 & 60 North Menantic Road.

This 1937 Quaint Cottage Style Home Was Renovat...

$625,000 Under Contract

4 Bateman Rd, Shelter Island

  • 2 Beds
  • 2 Baths
  • 0.57 Acres
  • 1,645 sqft

School District: Shelter Island

This 1937 Quaint Cottage Style Home Was Renovated In 2002, An Addition Including Great Room With Fireplace, Dining And Kitchen Was Added. Situated On .57 Acres In The Heart Of Shelter Island With Quiet Level Yard, Enjoy Through Your Bay Window Or From Your ...

A Gracious 4200 Sq.ft. Traditional Home With Fa...

REDUCED 7%

$1,299,000

13 Locust Woods Dr, Shelter Island

  • 6 Beds
  • 5 Baths
  • 2.1 Acres
  • 4,128 sqft

School District: Shelter Island

A Gracious 4200 Sq.ft. Traditional Home With Fabulous Amenities, On 2 Plus Park Like Acres. Renovated In 2017. Located At The End Of A Cul-de-sac, This Home Features A Beautiful Mahogany Wrap Around Porch And Decking, Stone Patios. A Magnificent 20 X 40 X...

Bright&sunny Contemporary With 2 Master Suites,...

REDUCED 5%

$950,000

1 Osprey Rd, Shelter Island

  • 4 Beds
  • 3 Baths
  • 1.12 Acres
  • 2,950 sqft

School District: Shelter Island

Bright&sunny Contemporary With 2 Master Suites,3 Full Baths,garage,full Unfinished Basement,automatic Propane Generator,beautifully Landscaped,fish Pond,wrap Around Porch,andersen Windows,skylights,redone 2y Ref.wood Floors,firelace In Liv.room,all Year Rou...

Waterfront Light Filled Modern With In-ground W...

REDUCED 9%

$1,495,000

15 Dickerson Dr, Shelter Island

  • 3 Beds
  • 3 Baths
  • 1 Acres
  • 3,257 sqft

School District: Shelter Island

Waterfront Light Filled Modern With In-ground Waterside Pool & Dock. Covered Porch Surrounds & Allows Access From Every Room & Elevated Views To The Water. Eat In Kitchen, Dining Area & Living Room All Look To The Water. Walkout Basement With Media Room& De...

Menantic Creek Front Home With 180' Deepwater D...

$1,699,500

13 Dickerson Dr, Shelter Island

  • 2 Beds
  • 2 Baths
  • 1.1 Acres
  • 1,642 sqft

School District: Shelter Island

Menantic Creek Front Home With 180' Deepwater Dock. This Home Offers Furnished Open Living Space With Waterview, 2 Bedrooms, 1 Bath And Loft Area On 1.1 Acres With Sepaprate Studio/office And Gunite Heate Pool. Excellent Location For Summer Or Year Round O...

Located In A Desirable Area Of Shelter Island K...

REDUCED 1%

$1,459,000

8 Crescent Way, Shelter Island

  • 4 Beds
  • 4 Baths
  • 1.1 Acres
  • 2,816 sqft

School District: Shelter Island

Located In A Desirable Area Of Shelter Island Known As Hay Beach, This New Traditional Home Is Ready For Its New Owner. The Home Offers An Open Floor Plan With Vaulted Ceilings, A Chef's Kitchen With A Large Island And Dining Area. The Master Suite Offers H...

This 1.2 Acre Cleared Property Shares A Quiet R...

Photo of Listing #2893727

$469,000 Under Contract

47 Lake Dr, Shelter Island

  • 1.2 Acres

School District: Shelter Island

This 1.2 Acre Cleared Property Shares A Quiet Road Situated Off Of Lake Dr. This Is A Beautiful Parcel Located Approximately One Block From Wades Beach And Fresh Pond. Build Your Dream Home On Shelter Island And Enjoy All That Nature Has To Offer In This Sm...

As Seen On Hgtv, A Surprising, Frank Lloyd Wrig...

$875,000

20 Terry Dr, Shelter Island

  • 4 Beds
  • 3 Baths
  • 0.52 Acres
  • 2,644 sqft

School District: Shelter Island

As Seen On Hgtv, A Surprising, Frank Lloyd Wright-inspired Contemporary W/deeded Beach & Mooring Rights. Spacious Light-filled Open Living Area, Unique Architectural Features, Living Room W/fireplace, 3 Bdrms+ Lg Den, 2.5 Baths, Incl Master Bdrm Suite W/sli...

Charming 1866 Shorewood Farmhouse On .72 Acres....

REDUCED 4%

$1,125,000 Under Contract

29a Osprey Rd, Shelter Island

  • 5 Beds
  • 3 Baths
  • 0.72 Acres
  • 3,000 sqft

School District: Shelter Island

Charming 1866 Shorewood Farmhouse On .72 Acres. Facing South And Perfectly Situated Overlooking Gracious Yard And Fenced In Garden. Cedar Shingled Roof And Siding Help To Maintain The Unique And Authentic Feel Of This Beauty. Light And Southerly Breezes Flo...

The Perfect Hamptons Alternative- 110 Ft Dock ...

REDUCED 7%

$4,595,000

66 Ram Island Dr, Shelter Island

  • 3 Beds
  • 4 Baths
  • 1.16 Acres

School District: Shelter Island

The Perfect Hamptons Alternative- 110 Ft Dock And Private Beach Situated Above Coecles Harbor. Enjoy The Afternoon Sea Breeze & Stunning Harbor Sunsets. Entertain In Style: Decorators Interior, Oversized Living Room, Chef's Kitchen, 3 Ensuite Bedrooms...

A Wonderful Opportunity To Build Your Dream Hom...

REDUCED 2% Photo of Listing #2816929

$725,000

65 Peconic Ave, Shelter Island

  • 1.19 Acres

School District: Shelter Island

A Wonderful Opportunity To Build Your Dream Home On This Large Parcel Of Land Located In Desirable Silver Beach With Views Of Peconic Bay And The Prevailing Southwest Breezes The Possibilities Are Endless. Imagine Sitting On Your Front Porch Watching The Su...

Turn Key, Mint, Exceptionally Built, Spacious, ...

$2,695,000

1 Landing Ln, Shelter Island

  • 4 Beds
  • 5 Baths
  • 1.02 Acres
  • 2,774 sqft

School District: Shelter Island

Turn Key, Mint, Exceptionally Built, Spacious, Light Filled, Waterfront Shingle Traditional With Pool + Dock In Quiet Private Community. Beautiful Waterviews! Also Boasts 2 Waterside Master Suites Each With Waterside Decks. Open Floor Plan With Excellent In...

Spacious Waterview 2 Bedroom, 2 Bath Co-op On B...

$425,000

15 Winthrop Rd, Shelter Island

  • 2 Beds
  • 2 Baths
  • 1,080 sqft

School District: Shelter Island

Spacious Waterview 2 Bedroom, 2 Bath Co-op On Beautiful Dering Harbor With New Heated Gunite Pool, Tennis, Basketball Courts And Deep Water Dock. Spacious Lobby With Gym, Memberships Available. The Grounds Are Lush On 7.9 Waterfront Acres. Rental Program Av...

In The Historic Village Of Dering Harbor, This ...

REDUCED 4% Photo of Listing #2651678

$790,000

7 Dering Woods Rd, Shelter Island

  • 3.1 Acres

School District: Shelter Island

In The Historic Village Of Dering Harbor, This 3.1 Acre Property Is Down A Scenic, Wooded, Private Lane. This Acreage Awaits Your New Home. Assured Of Privacy, One Side Of The Property Abuts A 17 Acre Preserve And Another Backs Up To The 6th Tee Box At Gard...

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