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: 37
Average Price: $1,952,459
Highest Price: $18,000,000
Lowest Price: $375,000

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EXPLORE SHELTER ISLAND

 

Daniel Gale Sotheby's Open Houses

$3,795,000

90 Peconic Ave 5 Beds, 4.00 Baths, 1.00 Acres
Open House Date/Time Sat Nov 30 2019 (11:00 AM to 1:00 PM)

$1,599,000

157 N Ferry Rd 8 Beds, 4.00 Baths, 0.87 Acres
Open House Date/Time Sat Nov 16 2019 (1:30 PM to 3:00 PM)

Shelter Island Homes For Sale

37 Properties Found. Page 1 of 1
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Bumble Bee Manor - Unquestionably One Of The Ma...

$18,000,000

Shelter Island

  • 10 Beds
  • 10 Baths
  • 3.2 Acres

School District: Shelter Island

Bumble Bee Manor - Unquestionably One Of The Magnificent Estates Of The East End. Luxurious Waterfront Residence Has It All: Coecles Harbor Dock, Infinity Edge Pool, Spa, Multi-story Pool House, Carriage House/garage, Lush Gardens And Tennis. The 16 Room...

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...

Bucolic English Country Inspired 2-acre Estate ...

$2,988,000

28 S Menantic Rd, Shelter Island

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

School District: Shelter Island

Bucolic English Country Inspired 2-acre Estate On Secluded Parcel. Classic Interior, Gracious Common Rooms, Fireplace, Coffered Ceilings, Gourmet Country Kitchen, Butler's Pantry With Wet Bar, Built-in Window Seat & Bookshelves. Expansive Pastoral Grounds W...

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 3-bedroom, 2-bathroom Home Is Exquisite; E...

$1,795,000

69 N Cartwright Rd, Shelter Island

  • 3 Beds
  • 2 Baths
  • 0.82 Acres
  • 1,425 sqft

School District: Shelter Island

This 3-bedroom, 2-bathroom Home Is Exquisite; Exuding As Sophisticated Attention To Detail Which Perfectly Balances Historical Features With Contemporary, Smart Home Amenities And Aesthetics. A Stunning Turnkey Home For Sale On Shelter Island Featuring An ...

This Beautiful Contemporary Has 3 Bedrooms, 2.5...

REDUCED 4%

$1,725,000

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...

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

REDUCED 10%

$1,325,000

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...

Now Is The Time To Create Your Waterfront Dream...

REDUCED 7%

$1,299,000

11 Dickerson Dr, Shelter Island

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

School District: Shelter Island

Now Is The Time To Create Your Waterfront Dream Home-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 & Weste...

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...

REDUCED 6%

$1,199,000 Under Contract

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...

Updated Contemporary Close To Beach. Modern Ope...

REDUCED 4%

$1,100,000

39 Lake Dr, 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 With Stainless Appliances. Two Guest Rooms On Main Floor, Master Upstairs And Lower Level Guest Suite (br, Bath, Lr And Kitchenette.) Home Sits Up From Road Surrounded By Trees...

This 1887 Carpenter Gothic Victorian Is As Swee...

$999,999

11 Spring Garden Ave, Shelter Island

  • 4 Beds
  • 2 Baths
  • 0.12 Acres
  • 2,268 sqft

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. Surrou...

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

$975,000

12 Tims Trl, 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 Water-view Silver Beach Expanded Ranch Is ...

REDUCED 10%

$899,000

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

REDUCED 4%

$819,000

18 Manhanset Rd, Shelter Island

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

School District: Shelter Island

This 3br/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...

This Victorian Cottage Captures The Romance Of ...

REDUCED 4%

$819,000

42 New York Ave, Shelter Island

  • 4 Beds
  • 3 Baths
  • 0.08 Acres
  • 1,985 sqft

School District: Shelter Island

This Victorian Cottage Captures The Romance Of Shelter Island's Sweet Sea Breezes In Every Room. Carefree Summers Begin The Moment You Step Into This Impeccably Maintained 4 Bedroom 3 Bath Home. A Sun-filled Living Room Invites Relaxation. Bright & Airy New...

Part Of Original Westmoreland Subdivision Nestl...

$799,000

2 Tims Trl, Shelter Island

  • 3 Beds
  • 2 Baths
  • 0.5 Acres
  • 1,456 sqft

School District: Shelter Island

Part Of Original Westmoreland Subdivision Nestled Amongst 70 Yr Old Pine Trees, Cedar Shingled Ranch Is On 1/2 Acre Park Like Setting. This Renovated Home Has 3 Brs, 2 Bths, Open Lr W/fireplace, Dr W/french Doors, Chef's Kitchen W/marble Counters, High End...

Best Value On Shelter Island!!! Complete Top To...

REDUCED 7%

$759,999

42 N Midway Rd, Shelter Island

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

School District: Shelter Island

Best Value On Shelter Island!!! Complete Top To Bottom Renovation. Must See!! 5 Bedrooms!!!2 Baths, Gourmet Kitchen Just Over 1 Acre In Center Of Shelter Island With Room For A Pool. Close To All Beaches, Bars, Restaurants, Golf. Many Rooms Overlook The Un...

Best Value On Shelter Island!!! Complete Top To...

$759,999

42 N Midway Rd, Shelter Island

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

School District: Shelter Island

Best Value On Shelter Island!!! Complete Top To Bottom Renovation. Must See!! 5 Bedrooms!!!2 Baths, Gourmet Kitchen Just Over 1 Acre In Center Of Shelter Island With Room For A Pool. Close To All Beaches, Bars, Restaurants, Golf. Many Rooms Overlook The Uni...

Enjoy Stunning Waterfront Sunsets, Surrounded B...

$748,000 Under Contract

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 Type Of Property Doesn't Become Available ...

$725,000

57 N Midway Rd, Shelter Island

  • 2 Beds
  • 1 Baths
  • 2.2 Acres

School District: Shelter Island

This Type Of Property Doesn't Become Available Very Often. This Property Is 2.2 Acres With A 2 Bedroom, One Bath Home With A Detached 1 Car Garage Located Along The Front Of The Property. Behind The Home Is A 4 Car Garage Which Is Amazing Storage Or A Great...

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...

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

Photo of Listing #3177712

$450,000

16 Osprey Rd, 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.

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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