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: $1,563,452
Highest Price: $6,900,000
Lowest Price: $350,000

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Daniel Gale Sotheby's Open Houses

$2,295,000

1 Tarkettle Rd 4 Beds, 6.00 Baths, 1.10 Acres
Open House Date/Time Fri Feb 23 2018 (2:00 PM to 3:30 PM)

$1,500,000

1 Sylvan Rd 4 Beds, 3.00 Baths, 1.00 Acres
Open House Date/Time Sat Feb 24 2018 (11:00 AM to 1:00 PM)

Shelter Island Homes For Sale

32 Properties Found. Page 1 of 1
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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...

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...

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 ...

The Exclusive Enclave Of Ram Island Continues T...

$2,999,000

139 N Ram Island Dr, Shelter Island

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

School District: Shelter Island

The Exclusive Enclave Of Ram Island Continues To Attract Bold And Ambitious Architecture, And This Meticulously Maintained Bayfront Home Was Designed By Italian Architect Maria-rosaria Piomelli, The First Woman Dean Of An Architecture School In The United S...

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...

Stunning Waterfront Contemporary Tucked Away On...

REDUCED 9%

$2,650,000

142g N Ferry Rd, Shelter Island

  • 4 Beds
  • 4 Baths
  • 3,500 sqft

School District: Shelter Island

Stunning Waterfront Contemporary Tucked Away On A Full Acre Of Land. Open Plan Combines Spacious Entry With Kitchen, Lr, Dining, Den, 1st Fl Br & Bath. Windows & Doors Offer Access To Outdoor Deck, Pool & Views Of Gardiner's Creek. Upstairs, A Mbr & 2 Addit...

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...

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.

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...

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 Wonderful Farmhouse Is Nestled Back Away ...

REDUCED 7%

$1,295,000

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,...

Gracious 4200 Sq.ft. Traditional Home With Fabu...

$1,200,000

13 Locust Woods Dr, Shelter Island

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

School District: Shelter Island

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 3...

Beautifully Renovated Home. Gourmet Kitchen,all...

$1,199,000

13 Locust Woods Dr, Shelter Island

  • 6 Beds
  • 5 Baths
  • 2.1 Acres

School District: Shelter Island

Beautifully Renovated Home. Gourmet Kitchen,all Hard Wood Floors ,crown Moldings,new Pool Liner,pump And Motor, Custom Mantels On Firplaces, Extensive Landsacaping. Too Many Details To List. This Is A Must See! Plenty Of Outside Entertaining Room!

Charming & Sophisticated, This Newly Constructe...

$998,000

63 N Midway Rd, Shelter Island

  • 3 Beds
  • 3 Baths
  • 0.92 Acres
  • 2,150 sqft

School District: Shelter Island

Charming & Sophisticated, This Newly Constructed Farmhouse Is Simply Perfect. Open Living Design W/maple Floors, Hickory Cabinets & Granite Countertops. Eat-in Chef's Kitchen Filled W/natural Light & Sliding Doors To Dining Deck. Mbr Suite W/luxurious Bath ...

Scenic & Updated W/open Vaulted Living Area, Ga...

$995,000

149 N Ferry Rd, Shelter Island

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

School District: Shelter Island

Scenic & Updated W/open Vaulted Living Area, Gas Fireplace, Dining & Eat In Kitchen W/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. 2 Car Garage & Large ...

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...

Surprising, Frank Lloyd Wright-inspired Contemp...

$950,000

20 Terry Dr, Shelter Island

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

School District: Shelter Island

Surprising, Frank Lloyd Wright-inspired Contemporary In Private Community W/deeded Beach & Mooring Rights. Spacious Light Filled Open Living Area, Well-crafted Unique Architectural Features. Living Room W/fireplace, 3 Bedrooms + Large Den, 2.5 Baths. Master...

Charming Ranch Situated In The Harbor View Acre...

NEW

$950,000

7 Terry Dr, Shelter Island

  • 3 Beds
  • 2 Baths
  • 0.63 Acres
  • 1,600 sqft

School District: Shelter Island

Charming Ranch Situated In The Harbor View Acres Section. Home Boasts 3 Bedrooms & 2 Full Bathrooms, Solar Panel System W/ 20k Backup Generator For Entire House. Pool Liner 2 Years Old & Aztek Decking Around Pool. Home Is Walking Distance To Private Beach/b...

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.

This 2.20 Acre Property Allows For So Many Poss...

$825,000

57 N Midway Rd, Shelter Island

  • 2 Beds
  • 1 Baths
  • 2.2 Acres
  • 1,546 sqft

School District: Shelter Island

This 2.20 Acre Property Allows For So Many Possibilities. Besides Having A 2 Bedroom, 1 Bathroom 1,546 Square Feet Home To Enjoy All Year Long, The Property Offers 1,221 Sq Feet Of Garage Spaces Which Includes 1 That Is Detached By The Home And Another 3/4 ...

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...

A Wonderful Opportunity To Build Your Dream Hom...

REDUCED 4% Photo of Listing #2816929

$695,000

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...

Calling All Artists & Professionals!!! Great ...

$649,900

152 N Ferry Rd, Shelter Island

  • 3 Beds
  • 3 Baths
  • 2 Acres
  • 1,622 sqft

School District: Shelter Island

Calling All Artists & Professionals!!! Great Opportunity To Have A Great Piece Of Property In Shelter Island With An Artist Studio/office Completely Separate And With It's Own Heat, Electric & Water. House Needs Work And With A Little Vision, It Can Be ...

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...

Wooded Level Building Lot In C Zone (residentia...

REDUCED 11% Photo of Listing #2936534

$350,000

17 N Midway Rd, Shelter Island

  • 1.01 Acres

School District: Shelter Island

Wooded Level Building Lot In C Zone (residential With Allowances) Bordering 60+ Acre Preserved Farm Currently A Horse Farm Near Menantic Creek And Close To Town And Public Beaches.

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