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: 38
Average Price: $1,585,276
Highest Price: $6,900,000
Lowest Price: $350,000

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Daniel Gale Sotheby's Open Houses

$2,995,000

39 Congdon Rd 3 Beds, 2.00 Baths, 1.29 Acres
Open House Dates/Times Sun May 20 2018 (12:00 PM to 2:00 PM) Sun May 20 2018 (12:00 PM to 2:00 PM)

$1,570,000

6 Quail Hedge Ln 4 Beds, 4.00 Baths, 0.95 Acres
Open House Date/Time Sat May 26 2018 (2:30 PM to 4:00 PM)

$1,500,000

1 Sylvan Rd 4 Beds, 3.00 Baths, 1.00 Acres
Open House Date/Time Sun May 20 2018 (2:00 PM to 4:00 PM)

$1,225,000

1 Cove Way 4 Beds, 3.00 Baths, 0.78 Acres
Open House Date/Time Sun May 20 2018 (11:30 AM to 1:30 PM)

Shelter Island Homes For Sale

36 Properties Found. Page 1 of 1
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The Exclusive Enclave Of Ram Island Continues T...

$2,975,000

139 Ram Island Dr, Shelter Island

  • 4 Beds
  • 3 Baths
  • 2.4 Acres

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...

Incomparable Waterfront Sunsets. Surrounded By ...

$835,000

48 Lake Dr, Shelter Island

  • 2 Beds
  • 1 Baths
  • 0.54 Acres
  • 1,105 sqft

School District: Shelter Island

Incomparable Waterfront Sunsets. Surrounded By Nature, Rare 100' Of Shoreline On 15-acre Fresh Pond, The 'jewel' Of Shelter Island Near Wades Beach. No History Of Flooding From Tide Or Storm Surge. Quaint 2 Bed, 1ba Ranch In Ideal Setting. Watch Ospreys Div...

Perfectly Situated On A Dead End, This Waterfro...

$2,995,000

39 Congdon Rd, Shelter Island

  • 3 Beds
  • 2 Baths
  • 1.29 Acres
  • 2,088 sqft

School District: Shelter Island

Perfectly Situated On A Dead End, This Waterfront Boasts More Than A Dock And A Panoramic View Of Congdon Creek. The House Is Surrounded On The South With A Variety Of Fruit Trees:apple,pear,cherry And Peach. Serenely Quiet, The Property Affords Natural Bea...

Step Back In Time To This Quaint, Beautifully R...

$975,000

20 Congdon Rd, Shelter Island

  • 3 Beds
  • 2 Baths
  • 0.71 Acres
  • 2,120 sqft

School District: Shelter Island

Step Back In Time To This Quaint, Beautifully Restored 3br Farmhouse Compound. 2nd Floor Spacious Mbr Plus 2 Bedrooms & Bath. Huge Rear Screen Porch & Enclosed Front Porch Add Living Spaces To An Already Roomy Formal Dr, Cozy Lr W/fp & Eik. Detached Garage ...

Stunning Location W/ Gorgeous Sunset Views Over...

$1,295,000

7 Gazon Rd, Shelter Island

  • 3 Beds
  • 3 Baths
  • 1.01 Acres
  • 1,901 sqft

School District: Shelter Island

Stunning Location W/ Gorgeous Sunset Views Over Sweeping Lawn Down To West Neck Creek. Home Set Up On Rise W/ Huge Lawn For Pool Or Tennis And Accessory Building Of Your Design. Water Views From Almost Every Room. Launch Your Kayak Or Peacefully Lounge W...

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

$925,000

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...

Private Drive To Large Treed Property On Lake, ...

$1,575,000

39 S Midway Rd, Shelter Island

  • 4 Beds
  • 3 Baths
  • 1.29 Acres
  • 2,200 sqft

School District: Shelter Island

Private Drive To Large Treed Property On Lake, Bucolic Waterfront Setting, Newly Renovated Incredible Modern Beach Cottage, 3 Waterside Bedrooms (including Spacious Master Suite) With Doors To Waterfront Patio, Lawn And Waterside Deck. Open Floor Plan Has B...

Charming Ranch Situated In The Harbor View Acre...

REDUCED 5%

$875,000

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...

Beautifully Renovated Home. Gourmet Kitchen,all...

REDUCED 4%

$1,149,000

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!

Dickerson Creek Waterfront Home Boasts An Open ...

$2,295,000

1 Tarkettle Rd, Shelter Island

  • 4 Beds
  • 6 Baths
  • 1.1 Acres
  • 4,200 sqft

School District: Shelter Island

Dickerson Creek Waterfront Home Boasts An Open Unobstructed Vista Of Wades Beach, North Haven And Beyond. This Light Filled Home With Vaulted Ceilings Gives You An Open Floor Plan, Offering Endless Opportunities To Enjoy And Entertain. The 1.1 Acre Property...

Surprising, Frank Lloyd Wright-inspired Contemp...

$950,000 Under Contract

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...

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 ...

Simply Perfect Modern On Private Acre W/plans F...

$1,850,000

6 Sunnyside Ave, Shelter Island

  • 4 Beds
  • 5 Baths
  • 0.94 Acres
  • 3,337 sqft

School District: Shelter Island

Simply Perfect Modern On Private Acre W/plans For Accessory Living In The Works. Open Lr, Dr & Eik W/dramatic Glass Walls To Mahogany Dining Deck In The Treetops. Master Br En Suite W/balcony. 3 Additional En Suite Brs. In-ground, Gunite Pool & Outdoor Show...

Charming & Sophisticated, This Newly Constructe...

REDUCED 5%

$949,500

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 ...

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

REDUCED 15%

$699,000

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 ...

Stunning Waterfront Contemporary Thoughtful Red...

REDUCED 13%

$2,295,000

142g N Ferry Rd, Shelter Island

  • 4 Beds
  • 4 Baths
  • 3,500 sqft

School District: Shelter Island

Stunning Waterfront Contemporary Thoughtful Redesign By Architects. Tucked Away On A Full Acre With Incredible Waterviews. Private Dock. Open Living Plan Combines A Henry Built Kitchen, Features Four Bedrooms And Four Full Bathrooms, A Wonderful Spacious Ou...

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...

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,...

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 ...

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...

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

REDUCED 11% Photo of Listing #2936534

$350,000 Under Contract

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.

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...

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

REDUCED 4%

$945,000 Under Contract

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.

The Perfect Hamptons Alternative- 110 Ft Dock ...

REDUCED 7%

$4,595,000

66 Ram Island Dr, Shelter Island

  • 4 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 4% Photo of Listing #2816929

$695,000 Under Contract

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...

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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