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: 36
Average Price: $1,880,775
Highest Price: $14,500,000
Lowest Price: $315,000

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EXPLORE SHELTER ISLAND

 

Shelter Island Homes For Sale

35 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
  • 3 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...

The Perfect Hamptons Alternative! 110 Ft Dock...

$3,992,000

66 Ram Island Drive, 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. Peter Pennoyer Designed, Decorators Interior, Oversized Living Room, New Chef's Kitchen, 3 Ensuite Bedroo...

Updated Contemporary Close To Beach. Modern Ope...

$1,150,000

39 Lake Drive, Shelter Island

  • 4 Beds
  • 4 Baths
  • 0.63 Acres
  • 2,436 sqft

School District: Shelter Island

Updated Contemporary Close To Beach. Modern Open Plan, Vaulted Ceilings, Kitchen W Stainless Appliances. Two Guest Rooms On Main Floor, 2nd Fl Master. Finished 1000 Sq Ft Lower Level W Bedroom, Den, Wet Bar And Walkout. Home Sits Up From Road Surrounded By ...

On Peconic Bay With 190 Feet Of Waterfront With...

$3,750,000

90 Peconic Avenue, Shelter Island

  • 5 Beds
  • 4 Baths
  • 1 Acres

School District: Shelter Island

On Peconic Bay With 190 Feet Of Waterfront With Sandy Beach, Bulkhead And Dock. This 5 Bedroom, 3.5 Bath Beautiful Shingle Beach House Enjoys Beautiful Sunsets, Magnificent Waterviews, Waterside Decks, Landscaped Lawn And Attached 2 Car Garage. Full Acre, M...

Island Getaway Farmhouse. Start Your Day With C...

$925,000

12 Tims Trail, Shelter Island

  • 4 Beds
  • 5 Baths
  • 0.5 Acres

School District: Shelter Island

Island Getaway Farmhouse. Start Your Day With Coffee On The Charming Porch. Enjoy Gatherings In The Sun Filled Open Kitchen, Dining Room & Family Room. Outside Entertaining Is Easily Accomplished On The Spacious Deck That Stepping Down To A Private, & Fence...

This Victorian Cottage Captures The Romance Of ...

$799,000

42 New York Avenue, Shelter Island

  • 4 Beds
  • 3 Baths
  • 0.08 Acres

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 ...

This Three Bedroom Silver Beach Cottage Is Surr...

$999,000

31 Peconic Ave, Shelter Island

  • 3 Beds
  • 1 Baths

School District: Shelter Island

This Three Bedroom Silver Beach Cottage Is Surrounded By Water With Stunning Views Of Peconic Bay From The Front Porch And Picturesque Pond In The Back. Open Kitchen, Dining Area And Living Room Take Advantage Of Every Water View. Wraparound Decks Creates A...

Beautifully Treed 1.38 Acres With Ranch Style H...

$695,000

68 S Ferry Road, Shelter Island

  • 3 Beds
  • 1 Baths
  • 1.38 Acres

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...

Sprawling Home On 2.3 Acres Overlooking The Ha...

$4,500,000

7 Lari Lane, Shelter Island

  • 4 Beds
  • 4 Baths
  • 2.3 Acres

School District: Shelter Island

Sprawling Home On 2.3 Acres Overlooking The Harbor& Bay W/ Nearly 300' Of Waterfront Including A, Private Boat Basin. The Home Is Designed To Take In All The Beauty Of Its Surroundings, With A Layout Perfect For Entertaining Or Simply Curling Up With A Goo...

Fully Renovated Classic Island Farmhouse W/ Mod...

$1,999,000

2 Bonnie Lane, Shelter Island

  • 5 Beds
  • 5 Baths
  • 4,500 sqft

School District: Shelter Island

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

Charming Clean Mid 20th Century Ranch On Shy Ac...

REDUCED 6%

$749,000

42 Brander Parkway, Shelter Island

  • 3 Beds
  • 1 Baths
  • 0.87 Acres
  • 1,176 sqft

School District: Shelter Island

Charming Clean Mid 20th Century Ranch On Shy Acre With Room For Swimming Pool. Recently Updated Kitchen. Open Layout Living And Dining Room. Three Season Sunroom For Your Plants And Morning Coffee. Mature Landscaping And Beautiful Garden. Beach Is A Thousan...

This Home Has Been Recently Renovated With An O...

$799,000

3 Wade Road, Shelter Island

  • 3 Beds
  • 2 Baths

School District: Shelter Island

This Home Has Been Recently Renovated With An Open Concept In The Main Area Of The Home Which Shows Off The Brand New Modern Kitchen Cabinets And Appliances. The Bathroom On The Upper Level Has An Elegant Feeling With An Rh Vanity And A Custom Shower. The L...

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

$849,900

40 Brander Parkway, Shelter Island

  • 3 Beds
  • 2 Baths
  • 0.75 Acres

School District: Shelter Island

Stylish, Mid-century Modern Ranch With 25' Private Sandy Beach On Peconic Bay. New Master Bedroom & Kitchen & Upgrades Throughout. Vaulted, Screened Dining Porch, Tiki Bar & 2 Decks For Entertaining. Smart Home W/new Oil Tank, Complete Insulation, Electric...

This Sun-filled Home Is Elevated And Is Situate...

$879,000

1 Osprey Road, Shelter Island

  • 4 Beds
  • 3 Baths
  • 1.12 Acres

School District: Shelter Island

This Sun-filled Home Is Elevated And Is Situated On 1.12 Acres Of Property Close To South Ferry, 3 Blocks From Wades Beach. The Cathedraled Living Room Creates An Open Feeling With Wood Burning Fireplace And Leads Into The Eat In Kitchen With Granite Counte...

1900's Farmhouse Located A Few Blocks From Coec...

$485,000

8 Burns Road, Shelter Island

  • 3 Beds
  • 1 Baths
  • 0.32 Acres

School District: Shelter Island

1900's Farmhouse Located A Few Blocks From Coecles Harbor Offering 3 Bedrooms 1 Bath On .32 Acres. In Addition A Shed With Electric And Water. Home Requires Upgrading, Make It Your Own.

Beautifully Renovated 1900's Victorian Style Ho...

$1,375,000

157 N Ferry Road, Shelter Island

  • 8 Beds
  • 4 Baths
  • 0.87 Acres

School District: Shelter Island

Beautifully Renovated 1900's Victorian Style Home Offers Open Plan Living With Grand Woodworking Details. The Eat In Kitchen Is Light Filled And Leads To The Spacious Deck, Great Space For Entertaining With Steps To The Gunite Pool. The 9' Ceiling Height On...

An Elegant Approach Leads To This Custom Creati...

$2,799,000

1 Dering Woods Lane, Shelter Island

  • 5 Beds
  • 6 Baths
  • 3.25 Acres

School District: Shelter Island

An Elegant Approach Leads To This Custom Creation On 3.25+/- Acres In Dering Harbor Village, Shelter Island. The 5-bedroom, 5.5-bath Residence Exudes Old World Charm With The Latest Amenities And A Light-filled Open Layout. Great Room, Cozy Den, Eat-in Kitc...

On A Beautiful 1.2 Acres With Stone Walls, Next...

$1,475,000

43 Lake Drive, Shelter Island

  • 4 Beds
  • 4 Baths
  • 1.2 Acres

School District: Shelter Island

On A Beautiful 1.2 Acres With Stone Walls, Next To Magnificent Wades Beach. Features; Wifi-enabled Heated Pool, Automatic Pool Cover, 700 Sq. Ft. Marble Patio. Two-story Entry Foyer With Staircase Leads To The Bedroom Areas. Two Master Bedroom Ensuites With...

Very Sunny Contemporary Home At The End Of A Ve...

$799,000

8 Fox Hollow Run, Shelter Island

  • 4 Beds
  • 2 Baths
  • 0.96 Acres

School District: Shelter Island

Very Sunny Contemporary Home At The End Of A Very Quiet Wooded Cul-de-sac . This Beautiful Shy Acre Lot Backs Up To Conservancy Estates. Home Inside Is In Excellent Condition With Hard Wood Floors, Open Floor Plan With Vaulted Ceilings. Mbr Has Private Deck...

The Only Unit Available In The Desirable Waterf...

$315,000

13 Winthrop Road # 29, Shelter Island

  • 1 Beds
  • 1 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 & ...

Enjoy Your 2020 Summer With Sunsets Galore And ...

$899,999

1 White Birch Place, Shelter Island

  • 3 Beds
  • 2 Baths
  • 0.86 Acres
  • 1,968 sqft

School District: Shelter Island

Enjoy Your 2020 Summer With Sunsets Galore And Sea Breezes From This Commanding 3 Bedroom/2 Bath Ranch. Short Walk To Multiple Town Landings And Shell Beach. Well Landscaped. Room For Pool.hand Sanitizer, Disinfecting Wipes, Disposable Gloves And Lysol A...

This Irreplaceable Estate On The Historic Isle ...

Photo of Listing #3141480

$1,295,000

32 Ram Island Drive, 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 ...

This Quiet Community Is The Perfect Place To Bu...

Photo of Listing #3195427

$335,000

8 Tim's Trail, Shelter Island

  • 0.62 Acres

School District: Shelter Island

This Quiet Community Is The Perfect Place To Build Your Shelter Island Dreams. Located Just Minutes From Bootleggers Alley Beach It's So Easy To Make Catching Spectacular Sunset Part Of Your Evening Routine. The Street Has Underground Electrical Line Giving...

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

Photo of Listing #3207729

$675,000

7 Dering Woods Road, 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 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 ...

Ultimate Privacy And Potential Await You On 5.5...

$1,700,000

72 S Ferry Road, Shelter Island

  • 1 Beds
  • 1 Baths
  • 5.5 Acres

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...

Solar Contemporary: Two Decks With Upper Deck O...

$2,150,000

13 Point Lane, Shelter Island

  • 4 Beds
  • 3 Baths
  • 0.9 Acres

School District: Shelter Island

Solar Contemporary: Two Decks With Upper Deck Off Of The Kitchen, Master Bedroom And Living Room, Lower Deck Off Of Family Room/den And Guest Rooms. Enjoy 150 Feet Of Waterfront, Sandy Beach And Water Views For Both The Sunrise And The Sunset. Four Bedrooms...

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

$2,500,000 Pending

5 Westmoreland Drive, 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 Pending

5 Westmoreland Drive, 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...

Renov 2-bdr Coop W/new Stainless Steel Kitc, Ne...

$375,000 Pending

Shelter Island

  • 2 Beds
  • 2 Baths

School District: Shelter Island

Renov 2-bdr Coop W/new Stainless Steel Kitc, New Tiled Bths, Hrdwd Flrs, Raised Ceilings, Skylights. Porch. Maint $2,300/mo Incls: Taxes, Coop Ins, Elect, Wtr, Cble, Heat, Gas, Snw Plwng, Bldg Exts., Lawns&gardens. Opt Rental Prog W/60% Net To Owner, 40% Ta...

Huge Opportunity To Build Your Dream Home On Be...

Photo of Listing #3177712

$450,000 Pending

16 Osprey Road, Shelter Island

  • 0.9 Acres

School District: Shelter Island

Huge Opportunity To Build Your Dream Home On Beautiful, Tranquil Shelter Island. Just Shy Of An Acre With Beach Rights And Private Tennis Court Use When Joining The Shorewood Civic Association.

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

$1,325,000 Pending

9 Wheeler Road, 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...

Magnificent Waterfront Victorian Built C. 1860 ...

$3,400,000 Pending

Shelter Island

  • 6 Beds
  • 5 Baths

School District: Shelter Island

Magnificent Waterfront Victorian Built C. 1860 With Guest Wing, Porch, Gazebo. 6 Brs, 4.5 Bths. Hist. Details: Marble Fpls, High Ceilings, Hrdwd Floors. Attic Is Playroom. Central A/c. Heated Gunite Pool Flanked By Flagstones, Outdoor Shower; Extensive Plan...

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