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SHELTER ISLAND, NY HOMES FOR SALE


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: $2,100,364
Highest Price: $14,500,000
Lowest Price: $315,000

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Shelter Island Homes For Sale

31 Properties Found. Page 1 of 1
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This Beautiful Contemporary Has 3 Bedrooms, 2.5...

$1,699,000

9 Point Lane, Shelter Island

  • 3 Beds
  • 2 Full Baths
  • 1 Half Baths

School District: Shelter Island

This Beautiful Contemporary Has 3 Bedrooms, 2.5 Baths And An Open Floor Plan Concept So That When You Enter The Home The 2 Story Living/dining Area Has A Stunning Water View Of Gardiners Bay And The North Fork. There Is A Water Side Deck Which Runs The Leng...

Beautifully Treed 1.38 Acres With Ranch Style H...

$695,000

68 S Ferry Road, Shelter Island

  • 3 Beds
  • 1 Full Baths

School District: Shelter Island

Beautifully Treed 1.38 Acres With Ranch Style Home And Pond. The Sun-filled Living Room Is Inviting And Leads To The Kitchen And Sunroom/den. In Addition, This Home Offers 3 Bedrooms And Full Bath With Shower. The Full Unfinished Basement Includes Utilities...

Stylish, Mid-century Modern Ranch With 25' Priv...

$899,000

40 Brander Parkway, Shelter Island

  • 3 Beds
  • 2 Full Baths

School District: Shelter Island

Stylish, Mid-century Modern Ranch With 25' Private Sandy Beach On Peconic Bay. Price Includes Waterfront Beach Strip At 54d Peconic Ave. Master Bedroom Ensuite With New Bath, Office/den & Laundry! 2 Guest Bedrooms Plus Full Bath. Vaulted, Screened Dining P...

The Only Unit Available In The Desirable Waterf...

$315,000

13 Winthrop Road # 29, Shelter Island

  • 1 Beds
  • 1 Full Baths

School District: Shelter Island

The Only Unit Available In The Desirable Waterfront Dering Harbor Inn! Situated On Approximately 8 Waterfront Acres Overlooking Dering Harbor. This Lovely Water-view Co-op Has 1br, 1ba, Eik, Lr & Waterside Elevated Terrace. New Padding/carpeting, Toilet & ...

This Irreplaceable Estate On The Historic Isle ...

Photo of Listing #3141480

$1,295,000

32 Ram Island Drive, Shelter Island

School District: Shelter Island

This Irreplaceable Estate On The Historic Isle Of Shelter Island Asserts A Total Of 9.74 Acres, Faces South, Boasts Over 1400' Of Road Frontage, & An Unbelievable 1/3 Mile Of Water Frontage! Directly On Coecles Harbor W/ 360 Degree Water Views Encompassing ...

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

Photo of Listing #3207729

$675,000

7 Dering Woods Road, Shelter Island

School District: Shelter Island

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

4.4 Beautiful Acres To Build Your Dream Home On...

REDUCED 7% Photo of Listing #3213265

$680,000

9 Willow Pond Lane, Shelter Island

School District: Shelter Island

4.4 Beautiful Acres To Build Your Dream Home On Shelter Island. The Property Has Views Of Willow Pond. Excellent Location Near Mashomack Preserve, Vine Street Cafe, And The South Ferry. Close To Downtown Sag Harbor Which Offers World Class Shopping, Dining,...

Enjoy This Elevated .54 Acre Building Lot Just ...

Photo of Listing #3214152

$469,000

20 Lake Drive, Shelter Island

School District: Shelter Island

Enjoy This Elevated .54 Acre Building Lot Just A Stones Throw From Wades Beach. The Lot Is Located Within A Quite Neighborhood, And Offers A Winter Water View Of Fresh Pond Lake. The Level Hilltop Offers A Natural Terrain That Is Architecturally Attractive...

Newly Built Custom Waterfront Home With Attenti...

$4,200,000

23 Freds Lane, Shelter Island

  • 5 Beds
  • 5 Full Baths
  • 2 Half Baths

School District: Shelter Island

Newly Built Custom Waterfront Home With Attention To Detail. Inground Heated Gunite Pool W/builtin Spa,seperate Heater And Automatic Pool Cover, Overlooking West Neck Creek. Oak Wood Floors Throughout. First Fr, Butlers Pantry, Chefs Kitchen W/sub Zero, ...

Come Explore This Beautiful Shingled Style Wate...

REDUCED 6%

$1,495,000

7 Dickerson Drive, Shelter Island

  • 4 Beds
  • 3 Full Baths

School District: Shelter Island

Come Explore This Beautiful Shingled Style Waterfront Home With A Stunning View Of Menantic Creek. This Delightful Home Is Situated On .5 Acres Offering A Well Manicured Yard With Privacy Hedge, Fenced Yard, A Separate Screened Garden Waiting For Your Plant...

On Peconic Bay Side Of Shelter Island Sound Wit...

$3,650,000

90 Peconic Avenue, Shelter Island

  • 5 Beds
  • 3 Full Baths
  • 1 Half Baths

School District: Shelter Island

On Peconic Bay Side Of Shelter Island Sound With 190 Feet Of Waterfront With Sandy Beach, Bulkhead And Dock. This 5 Bedroom, 3.5 Bath Beautiful Shingle Beach House On An Acre Enjoys Beautiful Sunsets, Magnificent Waterviews, Waterside Decks, Mature Landscap...

With A Breathtaking View East For Sunrises Towa...

$2,295,000

47L S Ferry Road, Shelter Island

  • 2 Beds
  • 1 Full Baths

School District: Shelter Island

With A Breathtaking View East For Sunrises Towards Taylor's Island And Sunsets To The West Through The Trees, This Amazing Property Won't Last. The Tranquility Of Coecles Harbor And The Remote Location Surrounds You With Amazing Wildlife. Make This Unique ...

Exceptional & Rare Opportunity To Build In A Co...

Photo of Listing #3239682

$920,000

5 Tuthill Drive, Shelter Island

School District: Shelter Island

Exceptional & Rare Opportunity To Build In A Coveted & Desirable Setting On Tuthill Drive On Big Ram Island. A 1.6 Acre Partially Cleared Parcel Awaits Your Custom Built Home With Year Round Water-views Of Coecles Harbor. A Short Distance To Reel Point, Bay...

Quintessential 1929 Stone Cape Style Beach Cott...

REDUCED 3%

$3,500,000

7 Little Ram Island Drive, Shelter Island

  • 4 Beds
  • 3 Full Baths

School District: Shelter Island

Quintessential 1929 Stone Cape Style Beach Cottage With Fantastic Waterviews, Waterside Screen Porch And Patio, 4 Bedrooms, 3 Baths, Beach, Dock, Bulkhead On 1.26 Acres Of Mature Landscaping. Cedar Knoll Hill Was Built When One Could Pick Any Property To B...

Immaculate Shingle Style Home W/stunning View, ...

$3,250,000

24 S Midway Road, Shelter Island

  • 5 Beds
  • 4 Full Baths

School District: Shelter Island

Immaculate Shingle Style Home W/stunning View, Walk-out To Water Lower Level And Architecture Of A 1940s Boathouse Lovingly Restored In 2016.4500 Sq Ft Across One-story House, Lower Level& Guest Apartment. No Detail Spared In To-the Studs Renovation; Includ...

Mansard Modern Beach House, 3 Bedrooms, 2.5 Bat...

$850,000

56 Lake Drive, Shelter Island

  • 3 Beds
  • 2 Full Baths
  • 1 Half Baths

School District: Shelter Island

Mansard Modern Beach House, 3 Bedrooms, 2.5 Baths, Open Floor Plan, Living Room With Fireplace, Dining Room And Den, Deck And Fenced Gunite Pool On Half Acre Which Adjoins Preserved Land And Fresh Pond. Ideal Location As It's Also Up The Street From Wades B...

Enjoy This Recently Renovated Cottage Style Hom...

REDUCED 3%

$675,000

6 W Thomas Street, Shelter Island

  • 2 Beds
  • 1 Full Baths
  • 1 Half Baths

School District: Shelter Island

Enjoy This Recently Renovated Cottage Style Home On 1/2 Acre Level Property. This Home Offers Lifeproof Floating Vinyl Floor Looks Like Wood. In Addition, Some Of The House Had Been Reinsulated And Sheetrocked, The Majority Of The Electric Was Rewired, New...

This Home Sits On A Very Private 1.2 Acres Of B...

NEW

$1,495,000

5 Quaker Path, Shelter Island

  • 4 Beds
  • 2 Full Baths
  • 1 Half Baths

School District: Shelter Island

This Home Sits On A Very Private 1.2 Acres Of Beautiful Shelter Island Property. The Privacy Is Enhanced By The Private Reserve Behind The Home. The Whole House Has Been Newly Renovated With Brand New Bedrooms, Bathrooms And A State Of The Art Kitchen. Beau...

:welcome Home! Well Maintained Wide Line Ranch ...

Pending

$980,000

13 Primrose Place, Shelter Island

  • 4 Beds
  • 3 Full Baths

School District: Shelter Island

:welcome Home! Well Maintained Wide Line Ranch On A Country Club Over Sized .87 Acre. Enjoy The In-ground Pool With Private Sitting Areas, Boasts Beautiful Hardwood Floors Throughout. Plenty Of Cabinet Space In The Updated Kitchen. Generous Sized Master Bed...

Come View This Newly Renovated Property, Locate...

Pending

$845,000

4 Marc Street, Shelter Island

  • 3 Beds
  • 2 Full Baths

School District: Shelter Island

Come View This Newly Renovated Property, Located On A Quiet Street . The Midcentury Style Home Includes 3 Bedrooms, 2 Full Baths, Two Deck Areas And A Large Screened In Porch. Separate Dining Room And Large Kitchen. There Is Also A Large Outdoor Shower And...

15 Terry Drive Is A Lovely Half Acre Lot In Sou...

Pending Photo of Listing #3240654

$449,000

15 Terry Drive, Shelter Island

School District: Shelter Island

15 Terry Drive Is A Lovely Half Acre Lot In Sought-after Harbor View Acres Neighborhood. At The End Of The Road Is The Private Association Beach & Water Access. Build Your Ideal Island Dream Home On Quiet Terry Drive And Keep Your Boat At A Mooring In West ...

Shelter Island Beach Oasis. Just Steps From The...

Pending

$1,195,000

11 Crab Creek Road, Shelter Island

  • 5 Beds
  • 3 Full Baths

School District: Shelter Island

Shelter Island Beach Oasis. Just Steps From The Beach This Spacious 5 Bedroom 3 Bath Colonial Will Create Summer Memories For Generations To Come. Enjoy Morning Coffee In The Three Season Porch Overlooking The Lush Landscaping. Open The French Patio Doors F...

Adorable Craftsman Style 3br/1.5ba Cottage Cent...

Pending

$595,000

142D Orchard Road, Shelter Island

  • 3 Beds
  • 1 Full Baths
  • 1 Half Baths

School District: Shelter Island

Adorable Craftsman Style 3br/1.5ba Cottage Centrally Located. Access To Gardiner's Creek At The End Of The Private Road For Your Kayak. Lr W/fp & Built-in Book Shelves Opens To The Formal Dr. The First Floor Also Hosts 2 Brs, Full Ba, 3 Season Porch, Kitche...

Stunning 2.49 Acre Waterfront On Little Ram Isl...

Pending

$3,850,000

32 Little Ram Island Drive, Shelter Island

  • 5 Beds
  • 4 Full Baths
  • 1 Half Baths

School District: Shelter Island

Stunning 2.49 Acre Waterfront On Little Ram Island With Main House, In-ground Waterside Pool, 109' Dock & Guest Accessory Living Quarters W/ 2-car Garage. Room For Tennis And More. Vaulted Living Room W/fireplace Plus A Wall Of Windows To The Water In Open ...

Amazing Waterfront Home On 1.15 Acres. This Pro...

Pending

$2,350,000

18 Margarets Drive, Shelter Island

  • 4 Beds
  • 3 Full Baths
  • 1 Half Baths

School District: Shelter Island

Amazing Waterfront Home On 1.15 Acres. This Property Offers It All, A Salt Water Pool With Waterview, Your Own Dock Approx. 8 Years Old And A Well-maintained Landscaped Property. The 1st Floor Offers Open Plan Living With Double Sided Fireplace And Sliding ...

Take In Sweeping Views Of Gardiners Bay From Th...

Pending

$4,995,000

189A Ram Island Drive, Shelter Island

  • 6 Beds
  • 6 Full Baths
  • 1 Half Baths

School District: Shelter Island

Take In Sweeping Views Of Gardiners Bay From This 6 Bedroom, 7 Bath Custom Built Waterfront Home Located At The End Of Shelter Island's Coveted Ram Island Drive. The 1.3 Acre Property Features A 20x45 Gunite Pool, Manicured Gardens, 122 Feet Of Sandy Bay Be...

This Victorian Cottage Captures The Romance Of ...

Pending

$799,000

42 New York Avenue, Shelter Island

  • 4 Beds
  • 3 Full Baths

School District: Shelter Island

This Victorian Cottage Captures The Romance Of Shelter Island's Sweet Sea Breezes In Every Room. Carefree Living Begins The Moment You Step Into This Impeccably Maintained 4 Bedroom 3 Bath Home. A Sun-filled Living Room Invites Relaxation And Peace. Bright ...

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