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: 39
Average Price: $1,820,679
Highest Price: $6,900,000
Lowest Price: $260,000

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Shelter Island Homes For Sale

38 Properties Found. Page 1 of 1
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Level And Lush With Many Salvageable, Mature Tr...

Photo of Listing #2970344

$260,000

4 Tims Trl, Shelter Island

  • 0.62 Acres

School District: Shelter Island

Level And Lush With Many Salvageable, Mature Trees, This Property Is Located In Desirable Long View. The Street Is Quiet And Peaceful. The Homes Are Lovingly Kept With Meticulous Care. It Is A Perfect Place To Start The Next Day Of The Rest Of A Life. Near ...

This Wonderful Farmhouse Is Nestled Back Away ...

REDUCED 90%

$1,395,000

18 Sunshine Rd, Shelter Island

  • 4 Beds
  • 3 Baths
  • 0.91 Acres
  • 2,600 sqft

School District: Shelter Island

This Wonderful Farmhouse Is Nestled Back Away From Neighbors Overlooking A Preserved Meadow. It Gives The Feel Of An Authentic Farmhouse Yet It Affords The Comfort And Luxury Of A New Home. Near To Fresh Pond, Wades Beach And The Convenience Of The Center,...

1900 Scenic Farmhouse, Restored & Updated. Open...

$1,049,000

149 N Ferry Rd, Shelter Island

  • 3 Beds
  • 3 Baths
  • 0.87 Acres
  • 2,691 sqft

School District: Shelter Island

1900 Scenic Farmhouse, Restored & Updated. Open Vaulted Living With Gas Fireplace, Dining & Eat In Kitchen & Gracious French Doors To Dining Deck. Mbr Suite & Office On First Floor, 2 Guest Bedrooms & Bath Above. Room For A Pool On The Spacious .87 Property...

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 ...

Gardiner's Bluff: Quintessential Beach Cottage ...

$3,950,000

85 Ram Island Drive, Shelter Island

  • 5 Beds
  • 5 Baths
  • 2.94 Acres

School District: Shelter Island

Gardiner's Bluff: Quintessential Beach Cottage On Shy 3 Acres W/ Great Bay Views. 258' Of Sandy Beach, Bulkhead, Waterside Heated 20 X 40' Gunite Pool W/ Slate Patio, Waterside Decks & Screened Porch, Open Floor Plan W/ Bedroom Suites On Both Floors, Den, G...

Saltbox Modern In South Ferry Hills With Associ...

REDUCED 14%

$799,000

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...

Quintessential Beach Cottage On Shy 3 Acres Wit...

$3,950,000

85 Ram Island Drive, Shelter Island

  • 5 Beds
  • 5 Baths
  • 2.94 Acres

School District: Shelter Island

Quintessential Beach Cottage On Shy 3 Acres With Great Bay Views. 258' Of Sandy Beach, Bulkhead, Waterside Heated 20 X 40' Gunite Pool With Slate Patio, Waterside Decks And Screened Porch, Open Floor Plan With Bedroom Suites On Both Floors, Den, Grand Maste...

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 Originally Built In 1888 And Renovated In 2010. Features Include Scenic Views Of Dering Harbor, 600 Ft Of Private Beach And A 168 Ft Deep Water Dock And A Deeded Moori...

Picturesque, Newly Renovated Farmhouse, Perfect...

$1,575,000 Under Contract

5 Sunshine Rd, Shelter Island

  • 4 Beds
  • 4 Baths
  • 0.9 Acres
  • 2,215 sqft

School District: Shelter Island

Picturesque, Newly Renovated Farmhouse, Perfectly Situated On A Shy, Scenic Acre. Chef's Eik W/walkout To Dining Patio, Cozy Lrw/fp, Fml Dr, & New Screen Porch For Comfortable Summer Evenings. New Mbr Suite, Guest Suite W/view To Pool, 2 Br & Ba Allow For P...

This Beautiful Newly Built Traditional Is A Mus...

$4,950,000

23 Freds Ln, Shelter Island

  • 5 Beds
  • 7 Baths
  • 1.1 Acres
  • 5,200 sqft

School District: Shelter Island

This Beautiful Newly Built Traditional Is A Must See And Offers A Water View From Most Rooms. There Are Many Amenities Including Chef's Kitchen, Formal Dining Room, Living Room And Den With Fireplaces, Master Bedroom En-suite On The 1st Floor, With 4 Addit...

On Desirable Big Ram Island, The Meandering Sto...

REDUCED 12%

$3,495,000

139 N Ram Island Dr, Shelter Island

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

School District: Shelter Island

On Desirable Big Ram Island, The Meandering Stone Driveway With Belgium Block Apron Leads You To This Private Contemporary Home In An Incomparable Setting. There Are Exquisite Unobstructed Views Of Gardiner's Bay, Bug Lighthouse & Plum Island From Most Room...

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.

Exceptional 6 Acre Farm In The Heart Of Shelter...

REDUCED 14%

$2,995,000

79 N Midway Rd, Shelter Island

  • 6 Beds
  • 6 Baths
  • 6.1 Acres
  • 6,494 sqft

School District: Shelter Island

Exceptional 6 Acre Farm In The Heart Of Shelter Island. 6 Bedroom Shingled Manor Style House With 4 Full And 2 Half Baths. Guest House With 2 Bedrooms, Full Kitchen, 2.5 Bathrooms, Over A 3 Car Garage. Center Aisle Barn With 3 Stalls, Hayloft, Tack Room A...

This Beautiful 1.3 Acre Parcel In Desirable Sho...

Photo of Listing #2937812

$550,000

25 Osprey Rd, Shelter Island

  • 133 Acres

School District: Shelter Island

This Beautiful 1.3 Acre Parcel In Desirable Shorewood Is A Perfect Location To Build The "happy Ever After" Home. It Is Level Yet Beautifully Treed. It Is Large Enough To Accommodate A House, A Pool And Even A Tennis Court. Shorewood Is Private And Quiet; T...

This 1937 Quaint Cottage Style Home Was Renovat...

$625,000

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 ...

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...

Inspired By An 1893 Dering Harbor Home, This 3....

$4,700,000

1 Dering Woods Ln, Shelter Island

  • 5 Beds
  • 6 Baths
  • 3.25 Acres
  • 5,400 sqft

School District: Shelter Island

Inspired By An 1893 Dering Harbor Home, This 3.25 Acre Dering Harbor Estate Boasts A Classic Interior With An Open Floor Plan Of Approximately 5400 Sf. Features Include: Double Height Coffered Ceilings, Wood Burning Fireplaces, Paneled Walls, And A Designer...

Located In Desirable Area Known As Hay Beach Th...

$1,479,000

8 Crescent Way, Shelter Island

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

School District: Shelter Island

Located In Desirable Area Known As Hay Beach This New Traditional Home Is Scheduled To Be Finished In June 2017. The Home Offers An Open Floor Plan With Vaulted Ceilings, A Chef's Kitchen With A Large Island. The Master Suite Offers His/hers Closets, Sinks ...

Turn-key Traditional Open Floor Plan & 20'x40'p...

REDUCED 6%

$1,590,000 Under Contract

26 Country Club Dr, Shelter Island

  • 4 Beds
  • 5 Baths
  • 1 Acres
  • 3,750 sqft

School District: Shelter Island

Turn-key Traditional Open Floor Plan & 20'x40'pool On Club Golf Course. Front Parlor Leads To Formal Lrw/fp & French Doors To Rear Deck. Formal Dining Room, Chef's Kitchen Then Sitting Area To Sliding Doors To Poolside Deck. First Floor Office, Laundry & Fu...

Centrally Located On Shelter Island, Emerges Th...

REDUCED 6%

$595,000

16 Bowditch Rd, Shelter Island

  • 3 Beds
  • 2 Baths
  • 0.31 Acres
  • 1,450 sqft

School District: Shelter Island

Centrally Located On Shelter Island, Emerges This Charming Three Bedroom Home With A Multitude Of Upgrades And Complimentary Renovations Throughout. A Granite Kitchen With New Appliances & Breakfast Bar. A New Master Bedroom, Ensuite With His & Her Closets...

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...

0.34 Acre Of Buildable Land. Located Next To An...

Photo of Listing #2893796

$350,000

10 Tennis Court Ln, Shelter Island

  • 0.34 Acres

School District: Shelter Island

0.34 Acre Of Buildable Land. Located Next To An Existing Home At 10 Tennis Ct Lane. Only 2 Homes From The Water On 2 Sides. 2nd Floor Waterviews. Directly Opposite A Preserve So Views Preserved Forever! Residential A Zone. Fantastic One Of A Kind Opportunit...

Gorgeous Location On The 14th Tee Of Gardiner's...

REDUCED 4%

$945,000

44 Country Club Dr, Shelter Island

  • 4 Beds
  • 3 Baths
  • 1 Acres
  • 2,097 sqft

School District: Shelter Island

Gorgeous Location On The 14th Tee Of Gardiner's Bay Country Club For This 4br/3ba Contemporary Home. Living Room With Fireplace, Den, Formal Dining Room & Eik. 2 Car Attached Garage. Room For A Pool. Quiet & Peaceful Neighborhood.

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

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 Island Retreat ! 110 Ft Dock And ...

REDUCED 8%

$4,950,000

66 Ram Island Dr, Shelter Island

  • 3 Beds
  • 4 Baths
  • 1.16 Acres

School District: Shelter Island

The Perfect Island Retreat ! 110 Ft Dock And Private Beach Situated Above Coecles Harbor. Enjoy The Afternoon Sea Breeze And Stunning Harbor Sunsets. Entertain In Style : Decorators Interior, Oversized Living Room, Chef's Kitchen, 3 Ensuite Bedroom...

Waterfront Modern At Water's Edge With Dock, Wa...

REDUCED 5%

$1,375,000

142h N Ferry Rd, Shelter Island

  • 4 Beds
  • 5 Baths
  • 0.37 Acres
  • 3,017 sqft

School District: Shelter Island

Waterfront Modern At Water's Edge With Dock, Waterside; Wrap Around Dining Deck, Pergula + 2nd Floor Verandas In Bucolic Setting. Quiet + Across From Large Waterfront Preserve. Spacious, Stylish + Recently Renovated, Italian Custom Cabinetry, Open Kitchen, ...

4 Rolling Acres With Incredible Elevation. Enjo...

Photo of Listing #2834985

$889,000 Under Contract

131 B S Midway Rd, Shelter Island

  • 4 Acres

School District: Shelter Island

4 Rolling Acres With Incredible Elevation. Enjoy The Summer Southwest Summer Breezes On This Incomparable Hilltop. Use Your Creativity And Create Your Very Private Summer Or Year Round Estate. Electric, Cable & Verizon In Place. Owner Willing To Hold Paper....

This Listing Is A Very Rare Find Because The Pr...

$1,149,000

56 Brander Pky, Shelter Island

  • 2 Beds
  • 1 Baths
  • 1.9 Acres
  • 1,200 sqft

School District: Shelter Island

This Listing Is A Very Rare Find Because The Property Has Front Yard And Backyard Water Views On 1.7 Acres Along With A Beach Lot That Is 25ft Wide X Approx. 118ft Long Located On Peconic Ave.

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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