Shelter Island Real Estate, Homes and Condos for sale

All Shelter Island homes currently listed for sale in Shelter Island as of 08/22/2019 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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$3,992,000
66 Ram Island Dr, Shelter Island NY 11964
4
BEDS
4
BATHS
2,800
SQFT
$1,426
$/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."
* PRICE LOWERED - $4,295,000 TO $3,992,000 
$2,988,000
28 S Menantic Rd, Shelter Island NY 11964
4
BEDS
5
BATHS
4,174
SQFT
$716
$/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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $3,199,000 TO $2,988,000 
$2,195,000
47 Peconic Ave, Shelter Island NY 11964
3
BEDS
4
BATHS
3,137
SQFT
$700
$/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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,485,000 TO $2,195,000 
$2,100,000
139 Ram Island Dr, Shelter Island NY 11964
4
BEDS
3
BATHS
2.40
ACRES
1985
BUILT
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,249,000 TO $2,100,000 
$1,799,000
9 Point Ln, Shelter Island NY 11964
3
BEDS
3
BATHS
2,972
SQFT
$605
$/SQFT
2.53
ACRES
1995
BUILT
"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 Length Of The Home, Every Bedroom Has A Water View. The Home Interior Was Recently Painted And The Wood Floors Have Been Finished."
* LISTED OVER 120 DAYS 
$1,565,000
9 Wheeler Rd, Shelter Island NY 11964
5
BEDS
4
BATHS
0.78
ACRES
2003
BUILT
"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 1/2 BA next to Front Door. Master on 1st with 9' ceilings and Whirlpool Bath w Separate Shower. Second Floor has 4BR/2BA Wall-Wall carpets in BRs. WD. Pull down access to Attic Storage. Finished Bsmt, with Office TV room & Gym."
* PRICE LOWERED - $1,625,000 TO $1,565,000 
$1,395,000
11 Dickerson Dr, Shelter Island NY 11964
3
BEDS
4
BATHS
3,300
SQFT
$423
$/SQFT
1.30
ACRES
1987
BUILT
"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 Around The Stone Fireplace. Open Loft Area On Second Floor Overlooks LR & Creek. Property Has Mature Plantings w/ Specimen Trees & Garden Shed. Generator, Private Legacy Dock & Lift w/ Electric & Water. Potential for a Pool See Site Plan ."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,595,000 TO $1,395,000 
$1,275,000
3 Conrad Rd, Shelter Island NY 11964
4
BEDS
3
BATHS
1,895
SQFT
$673
$/SQFT
0.70
ACRES
1983
BUILT
"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 & Bertazonni appliances set the tone of uncompromising quality with finishes that are top of the line across the board. Step out of your 20 x 40 heated gunite pool, a quick pass through your outdoor shower and walk 5 minutes to boat or Salt Restaurant."
$1,185,000
39 Lake Dr, Shelter Island NY 11964
4
BEDS
4
BATHS
2,436
SQFT
$486
$/SQFT
0.63
ACRES
1991
BUILT
"Designer Renovated Contemporary With 4 Beds, 4 Baths & Pool. Few Blocks To Wades Beach. Bright Open Plan Living Room/Dining Room/Kitchen With Glass Doors And Windows Facing Mahogany Pool Deck And Lush Back Yard. Sits Up On A Hill In A Canopy Of Oaks With Flowering Cherry, Dogwood And Japanese Maple. Enjoy Sunsets, Breezes And Winter Water View Of Protected Fresh Pond Across Street. Hardwood Floors, Separate Guest Suite, Skylights In Pantry And 2 Bathrooms, Multiple Bonus Rooms. New CAC And Roof."
$999,000
11 Spring Garden Ave, Shelter Island NY 11964
4
BEDS
2
BATHS
0.12
ACRES
1887
BUILT
"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 up with a book in the comfortable living room with cozy fireplace. Spend lazy afternoons at the association beach club or enjoy the summer breezes on the screened porch. The bedrooms with amazingly charming balconies are peaceful retreats."
$995,000
2 Wheeler Rd, Shelter Island NY 11964
4
BEDS
4
BATHS
2,933
SQFT
$339
$/SQFT
0.57
ACRES
1985
BUILT
"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, hardwood floors, CAC & BR fans, large deck for entertaining, outdoor shower & possibly room for a pool. 1-car garage & main floor laundry as well as a full basement with cedar closet, a second laundry & new & well-maintained systems throughout"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,095,000 TO $995,000 
$899,000
2 Quail Run, Shelter Island NY 11964
3
BEDS
3
BATHS
2,228
SQFT
$404
$/SQFT
0.97
ACRES
2002
BUILT
"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, stainless eat-In kitchen, first-floor Master- suite, 2-car attached garage, and central air. The spacious living room that allows multiple sitting areas, wrap around porch and screened porch provide many opportunities for entertaining."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $935,000 TO $899,000 
$885,000
63 N Midway Rd, Shelter Island NY 11964
3
BEDS
3
BATHS
2,150
SQFT
$412
$/SQFT
0.92
ACRES
2017
BUILT
"Open design living w/maple floors, hickory cabinets & granite countertops. Stylish & sleek, this newly constructed farmhouse is simply perfect. Eat-in Chef's kitchen filled w/natural light & sliding doors to dining deck. Mbr suite w/luxurious bath & extensive closets. Generous acreage offers beautiful lawn w/room for a pool, hosts 1 car garage, shed, greenhouse, & fruit trees. All across from a 35 acre preserve."
$879,999
1 Osprey Rd, Shelter Island NY 11964
4
BEDS
3
BATHS
2,950
SQFT
$298
$/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  * PRICE LOWERED - $895,000 TO $879,999 
$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 Sandy 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!"
* LISTED OVER 120 DAYS 
$849,999
42 N Midway Rd, Shelter Island NY 11964
5
BEDS
2
BATHS
1,850
SQFT
$459
$/SQFT
1.09
ACRES
1967
BUILT
"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 Views of Trees, Bamboo & Nature from Sachem Woods and Surrounding Areas. The first Floor Features a Custom Gourmet Kitchen W/Medallion Inset Cabinets, a White Quartz Countertop & Bertazzoni SS Appliances. New Roof, Siding, Too Much to List!"
$849,000
18 Manhanset Rd, Shelter Island NY 11964
4
BEDS
3
BATHS
2,706
SQFT
$314
$/SQFT
0.77
ACRES
1978
BUILT
"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 gardens grace the front lawn. Interior spaces are welcoming, bright & new with appealing finishes & design. Extras: 2 ovens, wine frdge, htd garage, water softener, aprilair systems, generator, whole house air purification, safe & more"
* PRICE LOWERED - $894,000 TO $849,000 
$819,000
42 New York Ave, Shelter Island NY 11964
4
BEDS
3
BATHS
1,985
SQFT
$413
$/SQFT
0.08
ACRES
1880
BUILT
"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 kitchen open to the dining room offers a special place to gather with friends. Settle in with a good book on the precious side porch overlooking the private garden. Master bedroom with ensuite bathroom creates the perfect place to retreat."
* PRICE LOWERED - $849,000 TO $819,000 
$760,000
3 Wade Rd, Shelter Island NY 11964
3
BEDS
1
BATHS
1,785
SQFT
$426
$/SQFT
0.62
ACRES
1968
BUILT
"Rehabilitated mid century raised ranch on quiet street on tranquil shelter island. Many new upgrades. Room for a pool."
* LISTED OVER 120 DAYS 
$748,000
48 Lake Dr, Shelter Island NY 11964
2
BEDS
1
BATHS
1,105
SQFT
$677
$/SQFT
0.54
ACRES
1955
BUILT
"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 living room w/wood burning fireplace overlooks the pond for cozy winter evenings. A solid home w/sleeping porch, full basement & detached garage. No concern of flooding from tide or storm surge. Your personal touch makes this the perfect get away!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $795,000 TO $748,000 
$699,000
20F S Ferry Rd, Shelter Island NY 11964
3
BEDS
2
BATHS
1,161
SQFT
$602
$/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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $749,000 TO $699,000 
$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 
$685,000
3 Lakeview Dr, Shelter Island NY 11964
4
BEDS
2
BATHS
1,732
SQFT
$395
$/SQFT
0.55
ACRES
1982
BUILT
"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 gardens, the LR/DR, EIK, 2BR, BA, Elevated Deck w/Electric Awning all found on the upper floor with views to the treetops. The Den w/wood stove & walkout to gardens & patio, 2 BR, BA & Laundry are on the ground floor. All private and peaceful."
$375,000
13 Winthrop Rd 15, Shelter Island NY 11964
1
BEDS
1
BATHS
625
SQFT
$600
$/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 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."
* LISTED OVER 120 DAYS 
 
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