Shelter Island Real Estate, Homes and Condos for sale

All Shelter Island homes currently listed for sale in Shelter Island as of 12/13/2018 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Shelter Island homes for sale or other Shelter Island real estate, please contact us and one of our knowledgeable Shelter Island REALTORS® would be pleased to assist you.


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$5,950,000
85 & 90 Ram Island Dr, Shelter Island NY 11964
5
BEDS
5
BATHS
3,230
SQFT
$1,842
$/SQFT
2.94
ACRES
1995
BUILT
"Newly Renovated Interiors/Exteriors. Quintessential Beach Estate On Shy 3 Acres With Great Bay View, 258' Of Sandy Beach, Bulkhead, Waterside Heated 20'X40' Gunite Pool W/Slate Patio, Waterside Decks & Screened Porch, Open Floor Plan W/ Bedroom Suites On Both Floors, Den, Grand Master Suite With Veranda On 2nd Floor, Many Extras Include Guest Cottage & Extra Lot At #90 For A Dock."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $6,200,000 TO $5,950,000 
$5,950,000
85 Ram Island Dr, Shelter Island NY 11964
5
BEDS
5
BATHS
3,500
SQFT
$1,700
$/SQFT
2.94
ACRES
1995
BUILT
"Newly Renovated Interiors/Exteriors. Quintessential Beach Estate On Shy 3 Acres With Great Bay Views, 258' Of Sandy Beach, Bulkhead, Waterside Heated 20'*40' Gunite Pool With Slate Patio, Waterside Decks And Screened Porch, Open Floor Plan With Bedroom Suites On Both Floors, Den, Grand Master Suite With Veranda On 2nd Floor. Many Extras Include A Separate Guest Studio. One Big Perk, Includes A .12 Acre Parcel At 90 Ram Island Drive (Across The Street Facing Coecles Harbor) To Add A Boat Dock."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $6,200,000 TO $5,950,000 
$4,900,000
29 Winthrop Rd, Shelter Island NY 11964
6
BEDS
10
BATHS
1.71
ACRES
1888
BUILT
"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 Garage, Home Theater Room, Library, Outside Pizza Oven, Wine Cellar And A Pool."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $5,900,000 TO $4,900,000 
$4,295,000
66 Ram Island Dr, Shelter Island NY 11964
4
BEDS
4
BATHS
4,050
SQFT
$1,060
$/SQFT
1.16
ACRES
1996
BUILT
"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 Guest House W/ Lg Bedroom And Bath. Extraordinary Home For The Discerning Buyer. Seaplane Access From Nyc."
* LISTED OVER 120 DAYS 
$3,498,000
28 S Menantic Rd, Shelter Island NY 11964
4
BEDS
5
BATHS
4,174
SQFT
$838
$/SQFT
2.00
ACRES
1888
BUILT
"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. On The 2nd Floor Is The Master En-Suite With Office And Deck & 2 En-Suite Guest Rooms.It Includes A Trellis Walkway That Leads To The 2nd Floor The Carriage House, 2.5 Car Garage Below. The 18X60 Ft Pool, Flanked By Cabana & 1Br Guest House."
* NEW LISTING 
$2,495,000
139 N Ram Island Dr, Shelter Island NY 11964
4
BEDS
3
BATHS
2.40
ACRES
1985
BUILT
"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 States. This Two +/- Acre Hilltop Sanctuary Boasts Privacy And Spectacular Views Of Gardiners Bay. Copious Amounts Of Sunlight Pour Into The Living Room From Floor To Ceiling Windows And An Open Hallway On The Second Floor."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,595,000 TO $2,495,000 
$2,485,000
47 Peconic Ave, Shelter Island NY 11964
4
BEDS
4
BATHS
3,137
SQFT
$792
$/SQFT
1.92
ACRES
1970
BUILT
"Beautiful Sunsets From This Mint, Modern, Water-View Estate. Enjoy Heated Water-View Pool, 50+ Linear Ft Of Private, Sandy Beach, Water Garden & Electric Sunshade & Awning For Outside Comfort. Interiors Have Been Freshly Renovated Throughout. New Custom Kitchen W/Honed Carrera Countertops, Solid White Oak Interior Doors, New Baths & Master & Guest Bedroom Suites. Smart Home Features Include Nest Remote Thermostat, Smoke/Co2 Detectors & Security Cameras."
$2,095,000
2 Bonnie Ln, Shelter Island NY 11964
5
BEDS
5
BATHS
4,500
SQFT
$466
$/SQFT
1.90
ACRES
2000
BUILT
"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 Stone Fireplace, 1st Floor Master Suite, Swimming Pool With Stone Patio, Apple Orchard & Specimen Trees. Separate And Private 1 Bdrm/1 Bath Guest House W/ Great Room, Kitchen & Porch. Detached 3-Car Garage. Excellent Rental History."
$1,950,000
13 Brander Pky, Shelter Island NY 11964
5
BEDS
6
BATHS
3,868
SQFT
$504
$/SQFT
1.45
ACRES
2018
BUILT
"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 20X40 Gunite Pool. If This Sounds Amazing It Gets Better, Right Now The Finishes Could Be To Your Liking."
* LISTED OVER 120 DAYS 
$1,495,000
15 Dickerson Dr, Shelter Island NY 11964
3
BEDS
3
BATHS
3,257
SQFT
$459
$/SQFT
1.00
ACRES
1987
BUILT
"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 Lower Level With Great Room, Bedroom, Bath, Laundry & Mechanicals. Mahogany Deck Surrounds In-Ground Pool. Near Salt Restaurant & The Island Boatyard."
$1,475,000
6 Quail Hedge Ln, Shelter Island NY 11964
4
BEDS
4
BATHS
3,054
SQFT
$483
$/SQFT
0.95
ACRES
1999
BUILT
"Next To A Preserve, This Well-Appointed Home Is Turn-Key. Luxuriously Landscaped Grounds W/Heated Ig Pool, Pool House, Patio Surround W.Built-In Kitchen & Privacy. This Expansive 4Br Gem Boasts A Chef's Eik, 4 Season Porch W/Stove, Mbr Suite, Formal Dr W/Rumford Fp, Stylish Lr, 2 Car Garage. New Pool Liner, New Well, New Lenox Cac Units. Bordered By Preserved Land."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,570,000 TO $1,475,000 
$1,149,000
13 Locust Wood Dr, Shelter Island NY 11964
6
BEDS
5
BATHS
4,128
SQFT
$278
$/SQFT
2.10
ACRES
2000
BUILT
"At The End Of A Cul-De-Sac This Beautiful 4,200 Sf Post Modern Sits Elevated On A Hill With A Mahogany Wrap Around Porch,Stone Patios & Incredible Heated L Shaped Pool With A Stone Waterfall. If You're A Fan Of The Historic Shelter Island, This Will Flirt With Your Future. This Home, Although Only 18 Years Old, It Resembles The Layout Of A Historic Home Floor Plan And Yet Enough Space For Everyone. This Current Owner Has Renovated The Whole House From Top To Bottom. It Has It All."
* LISTED OVER 120 DAYS 
$1,149,000
13 Locust Woods Dr, Shelter Island NY 11964
6
BEDS
5
BATHS
2.10
ACRES
1999
BUILT
"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!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,199,000 TO $1,149,000 
$925,000
1 Osprey Rd, Shelter Island NY 11964
4
BEDS
3
BATHS
2,950
SQFT
$314
$/SQFT
1.12
ACRES
2001
BUILT
"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 Round Solarium,Minutes Away From Wade's Beach,Mashomack Preserve,South Ferry,Great Getaway Or Perfect Permanent Residency"
* LISTED OVER 120 DAYS 
$875,000
40 Brander Pky, Shelter Island NY 11964
3
BEDS
2
BATHS
1,454
SQFT
$602
$/SQFT
0.75
ACRES
1958
BUILT
"Crisp & Newly Redone Mid-Century Modern Ranch On .75 Acre Plus 25' Wide Private Beach Strip On Peconic Ave. Spacious, New Mbr Suite, New Kitchen & Updates Throughout, Including Complete Insulation, Oil Tank, Electric, Plumbing, Outdoor Shower & Smart Home Features. Vaulted, Screened Dining Porch, Outdoor Tiki Bar & Two Decks For Entertaining Fun!"
$835,000
48 Lake Dr, Shelter Island NY 11964
2
BEDS
1
BATHS
1,105
SQFT
$756
$/SQFT
0.54
ACRES
1955
BUILT
"Incomparable Waterfront Sunsets. Surrounded By Nature, Rare 100' Of Shoreline On 15-Acre Fresh Pond, The 'Jewel' Of Shelter Island Near Wades Beach. No Concern Of Flooding From Tide Or Storm Surge. Quaint 2 Bed, 1Ba Ranch In Ideal Setting. Watch Ospreys Dive To Catch Their Evening Meal. Entertain On Elevated Deck. Launch Your Kayak After Coffee To Catch Bass, Bluegill And Carp. Solid Home W/ Sleeping Porch, Full Dry Basement + Detached Garage. Your Personal Touch Makes This The Perfect Getaway."
* LISTED OVER 120 DAYS 
$749,000
20F S Ferry Rd, Shelter Island NY 11964
3
BEDS
2
BATHS
1,161
SQFT
$645
$/SQFT
0.50
ACRES
1985
BUILT
"Private Country Lane Setting Off South Ferry Rd. Spacious Open Ranch Floor Plan. Additional Garage Space On Lower Level With Garage Door."
$699,000
57 N Midway Rd, Shelter Island NY 11964
2
BEDS
1
BATHS
1,546
SQFT
$452
$/SQFT
2.20
ACRES
1925
BUILT
"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 The Home. Priced To Sell!"
* LISTED OVER 120 DAYS 
$384,000
13 Winthrop Rd 15, Shelter Island NY 11964
1
BEDS
1
BATHS
625
SQFT
$614
$/SQFT
1969
BUILT
"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, Yoga Facility Included In Monthly Charges Along W All Taxes, Utilities, Cable, Grounds Maintenance And Parking. Flexible For Rental Income, Personal Use Or Both. In Easy Distance Of Heights And Harborside Shopping And Dining."
* PRICE LOWERED - $395,000 TO $384,000 
 
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