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: 39
Average Price: $1,436,051
Highest Price: $8,995,000
Lowest Price: $375,000

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EXPLORE SHELTER ISLAND

 

Daniel Gale Sotheby's Open Houses

$1,599,000

157 N Ferry Rd 8 Beds, 4.00 Baths, 0.87 Acres
Open House Date/Time Sat Sep 21 2019 (10:00 AM to 12:00 PM)

$885,000

63 N Midway Rd 3 Beds, 3.00 Baths, 0.92 Acres
Open House Date/Time Sat Sep 21 2019 (2:30 PM to 4:00 PM)

Shelter Island Homes For Sale

39 Properties Found. Page 1 of 1
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Own A Piece Of Shelter Island History With This...

$8,995,000

108 Ram Island Dr, Shelter Island

  • 22 Beds
  • 18 Baths
  • 4.3 Acres
  • 11,465 sqft

School District: Shelter Island

Own A Piece Of Shelter Island History With This One-of-a-kind Waterfront Estate In The Hamptons. The 4.3+/- Acre Property Boasts Rolling Lawn, Old Specimen Trees, Stone Patios, A Tennis Court, And 800+/- Feet Of Water Frontage With A Private Sandy Beach, De...

The Perfect Hamptons Alternative- 110 Ft Dock A...

REDUCED 7%

$3,992,000

66 Ram Island Dr, Shelter Island

  • 4 Beds
  • 4 Baths
  • 1.16 Acres
  • 2,800 sqft

School District: Shelter Island

The Perfect Hamptons Alternative- 110 Ft Dock And Private Beach Situated On Coecles Harbor. Enjoy The Afternoon Sea Breeze & Stunning Harbor Sunsets. Entertain In Style: Decorators Interior, Oversized Living Room, Chef's Kitchen, 3 Ensuite Bedrooms Plus Gue...

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 Under Contract

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...

This Spectacular Waterfront Estate Home Located...

$1,950,000

54 Westmoreland Dr, Shelter Island

  • 5 Beds
  • 4 Baths
  • 1.11 Acres
  • 3,398 sqft

School District: Shelter Island

This Spectacular Waterfront Estate Home Located In The Exclusive Westmoreland Farm Features A Massive Deep Water Dock, Secluded Private 200 +- Foot Beach, Breath Taking Views Of West Neck Harbor And A Waterside Pool. Located On This Unique Waterfront Penins...

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...

Ultimate Privacy And Potential Await You On 5.5...

$1,700,000

72 S Ferry Rd, Shelter Island

  • 1 Beds
  • 1 Baths
  • 5.5 Acres
  • 1,800 sqft

School District: Shelter Island

Ultimate Privacy And Potential Await You On 5.5 Acres Of Rolling Lawns, Woods, Vegetable And Perennial Gardens, Fruit Trees And Large Stocked Pond All At The End Of A 1000' Private Driveway. Less Then A Mile From The South Ferry And A Short Distance To Wade...

Exceptional Waterfront Value! Light-filled Mode...

$1,495,000 Under Contract

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 ...

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

REDUCED 4%

$1,495,000

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...

Waterfront Property On Menantic Creek. Boasts 2...

REDUCED 13%

$1,395,000

11 Dickerson Dr, Shelter Island

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

School District: Shelter Island

Waterfront Property On Menantic Creek. Boasts 2 Waterfront Master En-suites.3rd Bedroom Has Water & Dock View. Floor To Ceiling Windows In Living Room & Dining Room. Surrounded By Water W/ Eastern & Western Light.the Living Room Centers Around The Stone Fir...

This Irreplaceable Estate On The Historic Isle ...

Photo of Listing #3141480

$1,295,000

32 Ram Island Dr, Shelter Island

  • 9.74 Acres

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 ...

Chic & Timeless Design Meet Efficient Modern Li...

$1,275,000

3 Conrad Rd, Shelter Island

  • 4 Beds
  • 3 Baths
  • 0.7 Acres
  • 1,895 sqft

School District: Shelter Island

Chic & Timeless Design Meet Efficient Modern Living In This Newly Renovated 4 Bedroom, 3 Bath Home. The Open Floor Plan Seamlessly Integrates With The Spacious & Private .7 Acre Property Creating An Ideal Entertaining Environment. Custom Cabinetry & Bertazo...

This 1887 Carpenter Gothic Victorian Is As Swee...

$999,000

11 Spring Garden Ave, Shelter Island

  • 4 Beds
  • 2 Baths
  • 0.12 Acres

School District: Shelter Island

This 1887 Carpenter Gothic Victorian Is As Sweet As Its Porch Swing And Blue 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 And Kitchen. Curl ...

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

REDUCED 9%

$995,000

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, ...

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

REDUCED 4%

$899,000 Under Contract

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,...

$879,999

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...

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 ...

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

REDUCED 5%

$849,000

18 Manhanset Rd, Shelter Island

  • 3 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...

Better Then Brand New Construction... This 5 Be...

$819,000

42 N Midway Rd, Shelter Island

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

School District: Shelter Island

Better Then Brand New Construction... This 5 Bedroom Cape Cod Was Completely Renovated From Top To Bottom W/400 Series Anderson Windows Allowing The House To Be Flooded With Daylight & The Cool Summer Breeze To Flow Through. Many Rooms Overlook The Unique V...

Scenic & Charming Cape In A Quiet Community W/p...

$799,000

7 Tims Trl, Shelter Island

  • 3 Beds
  • 2 Baths
  • 0.64 Acres
  • 2,115 sqft

School District: Shelter Island

Scenic & Charming Cape In A Quiet Community W/preserved Land Behind. Lr W/fp, Dr W/wood Stove & Eik Offer Open Floor Plan Living. Mbr On The First Floor Or Office/den. Mudroom W/washer/dryer Leads To 2 Car Garage And Back Deck To Pool. 2nd Floor Hosts 2 Lar...

Enjoy Stunning Waterfront Sunsets, Surrounded B...

$748,000

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...

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 ...

Conveniently Located, This 4br/2ba Contemporary...

$685,000

3 Lakeview Dr, Shelter Island

  • 4 Beds
  • 2 Baths
  • 0.55 Acres
  • 1,732 sqft

School District: Shelter Island

Conveniently Located, This 4br/2ba Contemporary Is On A Generous Half Acre W/room For A Pool. On The South Side Of The Island, It Is Just Minutes To South Ferry, Wades Beach, Mashomack Preserve, Fresh Pond & The Town Center. Surrounded By Mature Perenial Ga...

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

REDUCED 15% Photo of Listing #2651678

$675,000

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...

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

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...

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