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: 34
Average Price: $1,617,618
Highest Price: $9,750,000
Lowest Price: $335,000

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SHELTER ISLAND
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Shelter Island Homes For Sale

34 Properties Found. Page 1 of 1
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Dramatic Waterfront Estate With Sweeping Circul...

$9,750,000

108 Ram Island Dr, Shelter Island

  • 22 Beds
  • 18 Baths
  • 4.3 Acres
  • 12,142 sqft

School District: Shelter Island

Dramatic Waterfront Estate With Sweeping Circular Driveway, 12,142 Sq Ft Cedar Shake Manor House With Entry Foyer, 4 Hearths, Commercial Kitchen, Dr/ballroom, Lr/bar, Windowed Porch/sunroom, 4 Blue Stone Patios With Total 3523 Sq Ft, Sweeping Lawn To Tennis...

This Spectacular Se Facing Harbor Front Home Wa...

$5,300,000

15 Montclair Ave, Shelter Island

  • 4 Beds
  • 4 Baths
  • 0.53 Acres
  • 4,545 sqft

School District: Shelter Island

This Spectacular Se Facing Harbor Front Home Was Beautifully Designed And Renovated In 2014. There Are Stunning Views And Sunrises From Most Rooms. This Home Offers Many Amenities; A Guest Cottage With 2 Bedrooms, 2 Baths, Full Kitchen And Gym, A Heated Gun...

Stunning, With Ornately Landscaped Expansive Gr...

REDUCED 9%

$3,199,000

28 S Menantic Rd, Shelter Island

  • 4 Beds
  • 5 Baths
  • 2 Acres
  • 4,174 sqft

School District: Shelter Island

Stunning, With Ornately Landscaped Expansive Grounds,it Creates A Classic English Countryside Atmosphere. The 1st Floor Features An Open Living Area With French Doors To The Patio Garden, Formal Dining, Eat-in-kitchen With Butler's Pantry, Laundry & A Study...

Simply Stunning New Construction W/water Views ...

REDUCED 9%

$2,995,000

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, 100' Dock & Gunite, 18x36, Heated Pool. Living Rm W/fireplace Opens To Elevated Deck. Eat In Kitchen & Formal Dining Area Open To Dining Deck. Wa...

Secluded 2.7 Acres And Super Sunny Home With Be...

$2,500,000 Under Contract

5 Westmoreland Dr, Shelter Island

  • 3 Beds
  • 2 Baths
  • 2.7 Acres

School District: Shelter Island

Secluded 2.7 Acres And Super Sunny Home With Beautiful Waterfront And Stunning View. Cathedral Ceiling, Fireplace & 4 Skylights In Living Room With Multiple Sliders To Rear Deck And Yard. Master And One Bedroom W Sliders To Yard. House Built New In 1988 Wit...

Secluded 2.7 Acres Beautiful Waterfront And Stu...

Photo of Listing #3096711

$2,500,000 Under Contract

5 Westmoreland Dr, Shelter Island

  • 2.7 Acres

School District: Shelter Island

Secluded 2.7 Acres Beautiful Waterfront And Stunning View. There Is A House Nestled On Property Built New In 1988 With 8' High Ceilings In Basement. Hardwood Floors Throughout. Main Level Laundry. Tons Of Storage And Plenty Of Room For Expansion To Create Y...

This Spacious 4 Bedroom, 3 Bath Waterfront Mode...

REDUCED 11%

$2,225,000

16 Margarets Dr, Shelter Island

  • 4 Beds
  • 3 Baths
  • 1 Acres
  • 1,656 sqft

School District: Shelter Island

This Spacious 4 Bedroom, 3 Bath Waterfront Modern Has Dock (@5' @ Low Tide) And Waterview Heated 55' Gunite 2 Lane Swimming Pool With Beautiful Sunset Waterviews. Landscaped, Secluded And Elevated From Shore With Waterside Deck, Two Master Suites, Living Ro...

Fully Renovated Classic Island Farmhouse W/ Mod...

$2,095,000

2 Bonnie Ln, Shelter Island

  • 5 Beds
  • 5 Baths
  • 1.9 Acres
  • 4,500 sqft

School District: Shelter Island

Fully Renovated Classic Island Farmhouse W/ Modern Finishes On 2 Acres, Across From Preserved Land & Extensive Open Space. Wrap Around Covered Porch With Mahogany Deck & Screened Porch. Main House Consists Of 4 Bedrooms, 3.5 Baths, Chefs Kitchen With Ston...

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 Beautiful Contemporary Has 3 Bedrooms, 2.5...

$1,799,000

9 Point Ln, Shelter Island

  • 3 Beds
  • 3 Baths
  • 2.53 Acres
  • 2,972 sqft

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...

Silver Beach Waterfront Shy Of 1 Acre. 5br/3.5...

$1,625,000

9 Wheeler Rd, Shelter Island

  • 5 Beds
  • 4 Baths
  • 0.78 Acres

School District: Shelter Island

Silver Beach Waterfront Shy Of 1 Acre. 5br/3.5ba Home. Ist Floor Features Cathedral Ceilings W Skylights For A Bright Sun Filled Space. Hardwood Floors. Viking Stove Kitchen. Fp. Sliders Open To A 20x40 Gunite Pool Overlooking Floating Dock, 6' At Low Tide...

Exceptional Waterfront Value! Light-filled Mode...

$1,495,000

15 Dickerson Dr, Shelter Island

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

School District: Shelter Island

Exceptional Waterfront Value! Light-filled Modern With Dock And In-ground Waterside Pool. Covered Porch Surrounds & Offers Elevated Views To The Water & Access From Every Room. Living & Dining Rooms & Eat In Kitchen All Look To The Water. Waterside Walkout ...

Secluded Waterfront Property On Menantic Creek....

REDUCED 13%

$1,395,000

11 Dickerson Dr, Shelter Island

  • 3 Beds
  • 4 Baths
  • 1.3 Acres
  • 3,300 sqft

School District: Shelter Island

Secluded Waterfront Property On Menantic Creek. Boasts 2 Waterfront Master En-suites. 3rd Bedroom Also Has Water & Dock View. Floor To Ceiling Windows In Living Room And Dining Room. Surrounded By Water With Eastern & Western Light, The Living Room Centers ...

This Water-view Silver Beach Expanded Ranch Is ...

$1,095,000

2 Wheeler Rd, Shelter Island

  • 4 Beds
  • 4 Baths
  • 0.57 Acres
  • 2,933 sqft

School District: Shelter Island

This Water-view Silver Beach Expanded Ranch Is Much More Than Meets The Eye! Its Newly Constructed Addition Allows For A Large 4+br Home With Bonus Family Room W/water View; Or A Spacious 3-br Home With A 1+br Guest Suite W/wv. Bright, Airy & Fresh Spaces, ...

This 1887 Carpenter Gothic Colonial Is As Sweet...

REDUCED 5%

$999,000

11 Spring Garden Ave, Shelter Island

  • 4 Beds
  • 2 Baths
  • 0.12 Acres

School District: Shelter Island

This 1887 Carpenter Gothic Colonial Is As Sweet As Its Porch Swing & Hydrangeas. The Front Porch, Chapel Style Doors And Guest Parlor Welcome You To This Historic Home. Simple Gatherings Are Easy To Create In The Open Dining Room & Kitchen. Curl Up With A B...

Move In Ready -5 Bedroom Cape Cod Completely Re...

REDUCED 3%

$899,999

42 N Midway Rd, Shelter Island

  • 5 Beds
  • 2 Baths
  • 1.09 Acres
  • 1,850 sqft

School District: Shelter Island

Move In Ready -5 Bedroom Cape Cod Completely Renovated From Top To Bottom. New Roof, Hardy Clapboard Siding, 400 Series Anderson Windows, Solid Wood Doors, Hardwood Floors, 2 Propane Furnaces, 2 Cac, Tankless Hw Heater, Whole House Humidifier, Brazilian Ha...

Desirably Located Near Fresh Pond, Wade's Beach...

REDUCED 4%

$899,000

2 Quail Run, Shelter Island

  • 3 Beds
  • 3 Baths
  • 0.97 Acres
  • 2,228 sqft

School District: Shelter Island

Desirably Located Near Fresh Pond, Wade's Beach, Mashomack Preserve, And The South Ferry, A Gateway To The Hamptons, This Beautiful Move-in Ready Traditional Is Nestled Among Shade Trees And Offers Many Comforts Including A Stone Fireplace, Hardwood Floors,...

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

REDUCED 3%

$895,000

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...

This 4br/3ba Expanded Ranch Is Turnkey With A C...

$894,000

18 Manhanset Rd, Shelter Island

  • 4 Beds
  • 3 Baths
  • 0.77 Acres
  • 2,706 sqft

School District: Shelter Island

This 4br/3ba Expanded Ranch Is Turnkey With A Complete, New Renovation Throughout. Located Across From Sylvester Manor Farmlands, The Sunsets Are Spectacular Year Round Over The Fields. The Grounds Host An Expansive Backyard With Room For A Pool. Raised Bed...

Crisp & Newly Redone Mid-century Modern Ranch O...

$875,000

40 Brander Pky, Shelter Island

  • 3 Beds
  • 2 Baths
  • 0.75 Acres
  • 1,454 sqft

School District: Shelter Island

Crisp & Newly Redone Mid-century Modern Ranch On .75 Acre Plus 25' Wide Private Sandy Beach Strip On Peconic Ave. Spacious, New Mbr Suite, New Kitchen & Updates Throughout, Including Complete Insulation, Oil Tank, Electric, Plumbing, Outdoor Shower & Smart ...

Enjoy Stunning Waterfront Sunsets, Surrounded B...

$795,000

48 Lake Dr, Shelter Island

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

School District: Shelter Island

Enjoy Stunning Waterfront Sunsets, Surrounded By Nature, From This Quaint 2br, 1ba Cottage On Shelter Island's Lake, Known As "fresh Pond". Entertain On Your Waterside Elevated Deck & Launch Your Kayak After Breakfast For Some Freshwater Fishing. The Livin...

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...

Recently Upgraded With New Cedar Shingles, New ...

$785,000 Under Contract

17 Worthy Way, Shelter Island

  • 3 Beds
  • 3 Baths
  • 0.62 Acres
  • 2,852 sqft

School District: Shelter Island

Recently Upgraded With New Cedar Shingles, New Windows, New Appliances, Mahogany Deck, Ductless Ac/heating, 3 Bed, 2.5 Baths On .62 Acre In Longview, Belgian Block Driveway

This 2.2 Acre Property Allows For So Many Possi...

$699,000

57 N Midway Rd, Shelter Island

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

School District: Shelter Island

This 2.2 Acre Property Allows For So Many Possibilities. Besides Having A 2 Bedroom 1 Bath 1546 Sq Ft Home To Enjoy All Year Round, The Property Offers 1,221 Sq Ft Of Garge Spaces Which Includes 1 Detached Garage By The Home And 3/4 Car Garage Space Behind ...

Residental Wooded Level Vacant Lot In Waterfron...

Photo of Listing #3124158

$425,000

11 Margarets Dr, Shelter Island

  • 0.94 Acres

School District: Shelter Island

Residental Wooded Level Vacant Lot In Waterfront Neighborhood. Possible Second Floor Waterview As Waterfront Properties Across The Street. Opportunity To Own Withl With Waterfront Across The Street.

Spectacular Bay View 1 Bedroom, 1 Bath Unit Wit...

$375,000 Under Contract

13 Winthrop Rd 15, Shelter Island

  • 1 Beds
  • 1 Baths
  • 625 sqft

School District: Shelter Island

Spectacular Bay View 1 Bedroom, 1 Bath Unit With Porch In 7.9 Acre Dering Harbor Inn Waterfront Property. Bright And Roomy With Private Porch On Lawn With Adirondack Chairs Over Bluff And Association Dock. Heated Pool, Two Tennis Courts, Fully Equiped Gym I...

Half Acre Of Land In The Harbor View Acres Comm...

Photo of Listing #P1342121

$335,000 Under Contract

Shelter Island

  • 0.5 Acres

School District: Shelter Island

Half Acre Of Land In The Harbor View Acres Community Of Shelter Island. The Property Has A Private Association Beach With Picnic Tables And Water Access On West Neck Bay. Build Your Dream Home And Enjoy The Peace And Tranquility That Shelter Island Offers.

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