43 Homes For Sale in Shelter Island, NY

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$449,000Est. Payment
1 Bed | 1 Bath | -- Sqft
13 Winthrop Road #24, Shelter Island, NY 11965
House For Sale

Situated on almost eight acres of prime Shelter Island waterfront this beautifully renovated coop has a new kitchen with; granite counter tops, appliances and wood floors. Plus, a newly renovated tile bath with high end finishes. Located on the first floor for easy access and a lovely terrace with water views. The COOP offers: tennis, heated 50' x 24' gunite swimming pool, gym, and marina. Important consideration, $1,187. monthly Maintenance fee is all inclusive and includes, with no extra charges or fees, all of the following: real estate taxes, heat, hot water, air conditioning, electric, water, septic, refuse pickup, high speed WiFi, cable television, telephone, gym membership, all year round grounds maintenance, parking, snow plowing, heated pool, kayak racks, storage, 24 hour on-site property manager and a heated and secure storage area. An on-site deep water dockage with power and water is available at a discounted rate for owners. Exclusive: $449K. Dering Harbor Real Estate

$1,350,000Est. Payment
9.74 Acres
32 Ram Island Drive, Shelter Island, NY 11964
Lots Land For Sale

Beautiful Estate Setting On The Historic Isle Of Shelter Island. Asserting A Total Of 9.74 Acres, The Property Faces South Directly On Coecles Harbor, Encompassing An Unmatched 1/3 Mile Of Water Frontage, & 360 Degree Water Views Inclusive Of Gardiners Bay. Truly An Exceptional Property For Those Looking For Ultimate Privacy, & Relaxation!

$1,550,000Est. Payment
4 Beds | 3 Baths | 2,650 Sqft
1 Sylvan Road, Shelter Island, NY 11965
House For Sale

Superior Built Designer Showcase, Open Floor Plan, 4 bedrooms, 3 baths, near beach with heated saltwater gunite pool, pergula dining patio, fenced gardens with mature landscaping, deck with awning, outdoor shower, firepit, pool shed, attached garage, generator, Belgian block driveway with additional parking.

$1,885,000Est. Payment
4 Beds | 4 Baths | 3,300 Sqft
10 Grand Avenue, Shelter Island, NY 11964
House For Sale

Sitting majestically in the Heart of the Heights on 3 levels with Water Views from practically all rooms this well designed and beautifully maintained home is now available for sale. Bordering a park and with all the amenities your heart could desire for year round living. Enter through the lovely sunroon adjoining the living room with large bay picture window and a wood burning stove which leads through to the eat in kitchen, completing the first floor are two guest bedrooms (one en suite with waterviews) and two bathrooms. The second floor has a very spacious master bedroom with both private deck and a French balcony from which to watch the ebb and flow of Dering Harbor or feel the summer breezes. Master Bathroom has whirlpool tub and large shower, great sized walk-in closet. There is an open mezzanine library/ den space that overlooks living area. The walk out lower level has an additional guest room, office, space for a gym, art/pottery studio, laundry room and garage. With fenced in freeform pool and patio surrounded by plethora of wonderful flowering bushes in raised beds. The home has multi-level outdoor entertainment areas and a large round deck is the focal point by the kitchen for you and your loved ones to begin your story in this wonderful home. Please call with any questions or to make an appointment to view.

$4,995,000Est. Payment
6 Beds | 7 Baths | 5,500 Sqft
189a Ram Island Drive, Shelter Island, NY 11964
House For Sale

Take in sweeping views of Gardiners Bay from this 6 bedroom, 7 bath custom built waterfront home located at the end of Shelter Island's coveted Ram Island Drive. The 1.3 acre property features a 20x45 gunite pool, manicured gardens, 123 feet of sandy bay beach and a separate legal guest suite above the detached 2 car garage complete with bedroom, kitchen and full bath. Constructed with unparalleled craftsmanship, the main house features 5500 square feet of both open concept living and multiple spaces for work, movies and privacy. Once in a lifetime opportunity to live, work and entertain on the singularly spectacular Ram Island.

$2,995,000Est. Payment
5 Beds | 3 Baths | 4,220 Sqft
3 Bluff Avenue, Shelter Island Heights, NY 11964
House For Sale

This home is located at 3 Bluff Avenue Shelter Island Heights, NY 11964 US and has been listed on Homes.com since 11 January 2021 and is currently priced at $2,995,000, approximately $710 per square foot. This property was built in 1895. 3 Bluff Avenue is within the school district(s) Shelter Island Union Free School District with nearby schools including Shelter Island School. Similar properties nearby are <a href="/property/3-bluff-ave-shelter-island-ny-11964/id-400033223452/">3 Bluff Ave</a>, <a href="/property/24-s-midway-rd-shelter-island-ny-11964/id-400032794037/">24 S Midway Rd</a>, 90 Peconic Ave, <a href="/property/120-caiola-ct-greenport-ny-11944/id-1000027869648/">120 Caiola Ct</a>, <a href="/property/2055-albertson-ln-greenport-ny-11944/id-1000008235242/">2055 Albertson Ln</a>, 47b S Ferry Rd, <a href="/property/67925-county-road-48-greenport-ny-11944/id-1000068486386/">67925 County Road 48</a>, <a href="/property/62675-county-road-48-greenport-ny-11944/id-400022191149/">62675 County Road 48</a>, <a href="/property/751-laurel-ave-southold-ny-11971/id-1000038405249/">751 Laurel Ave</a>, and <a href="/property/shelter-island-ny-11964/id-400034282434/">5 Westmoreland Dr</a>.

$5,975,000Est. Payment
4 Beds | 4 Baths | 2,800 Sqft
62 Winthrop Road, Shelter Island, NY 11964
House For Sale

Nantucket style traditional situated on 3.36 acres over looking the beautiful sunsets of Dering Harbor and Salt Pond. Recently renovated, gourmet eat in kitchen, 4 bedrooms, 3.5 baths, living room with wood burning fireplace, hardwood floors, wrap around deck and porch with gazebo, approx. 52' x 22' heated gunite swimming pool, mature landscaping, 125' deep water boat dock and beach. Possible room for 1000 sq ft expansion. Exclusive: $5.975M Dering Harbor Real Estate

$595,000Est. Payment
3 Beds | 2 Baths | 885 Sqft
142d Orchard Road, Shelter Island, NY 11971
House For Sale

Adorable Craftsman style 3BR/1.5Ba Cottage centrally located. Access to Gardiner's Creek at the end of the private road for your kayak. LR w/FP & built-in book shelves opens to the formal DR. The first floor also hosts 2 BRs, Full BA, 3 season porch, Kitchen w/door to back yard & stairs up. The second floor has a large bedroom with half bath and lots of storage. Covered patio, shed for storage & spacious grounds all add to this Island charmer.

$7,750,000Est. Payment
7 Beds | 7 Baths | 5,793 Sqft
40b Stearns Point Road, Shelter Island, NY 11965
House For Sale

This soaring light filled home blends gently onto a majestic waterfront bluff, one of the highest points on Shelter Island centrally located above Crescent Beach - a perfect viewing spot for the annual Shelter Island Fireworks! Surrounded by almost four acres of wooded privacy, the property offers sweeping water views across the North Fork and beyond to the Connecticut shoreline, with glorious year round sunsets. Designed by architect Michael Haverland, the residence is a hybrid of a 1925 Shelter Island traditional beach house, juxtaposed perfectly with a 3400 square foot modern addition, for a total of over 6000 square feet of living space. Two elegant wings come together, their pitched roof lines and mullioned walls of glass blending seamlessly with the style of the original beach house. Delicate steel window frames are detailed as thin as possible, providing an abundance of natural light, allowing magnificent water views. The northwest facing bedroom wing provides separation and privacy from the rest of the house. The master bedroom suite's exposed steel beams support a vaulted ceiling with a full window wall of endless views. A second bedroom suite below with floor to ceiling windows offers similar stunning vistas. Both master and guest suites have attached dressing rooms. Each features a generous size stone and tiled bathroom complete with a luxurious soaking tub, glass enclosed shower and oversized wall hung double sinks. The living room wing faces north and west, also with exposed structural steel columns and beams serving as a counterpoint to a 23' gabled wall of glass. Polished limestone flooring balances with a two story fieldstone fireplace, customized with an inset flat screen for relaxing evening enjoyment. An inviting entrance foyer greets visitors with views through to the water, and serves to transition the modern to the original house, which has been extensively renovated.The 1925 living and dining room have been combined into an exp

$2,950,000Est. Payment
5 Beds | 5 Baths | 4,475 Sqft
24 S Midway Road, Shelter Island, NY 11964
House For Sale

This stunning freshly renovated waterfront home with detached guest apartment and garage could be your new refuge. The open plan living area with vaulted ceiling steps onto an oversize waterfront entertaining deck with sunset views and a private dock. Have it all with 2 master suites, 2 more guest bedrooms plus a private apartment, a chefs kitchen with high end appliances and quartz counters. Plenty of room for a gym, home office and separate kids play/study space. Spread out in 4475 square feet of living area across the main level, finished walkout basement and apartment. The classic brick chimney with double sided hearth serves the main living area and Master bedroom and also provides a pizza oven and hearth in the finished lower level living area. A full house generator for peace of mind plus room for a pool complete this move in ready bucolic dream property. It is only a short bicycle ride to the best area beach or to town for shopping and a bite at the great cafes!

$699,000Est. Payment
2 Beds | 1 Bath | 1,546 Sqft
57 North Midway Road, Shelter Island, NY 11964
House For Sale

This 2.2 acre property allows for so many possibilities. The 1,546 sq foot ranch style home that site on the property is a 2 bedroom, 1 bath. The property also offers 1,221 sq feet of garage space which includes a detached garage by the home and another 3+ garage space behind the home. Priced to sell!

$850,000Est. Payment
-- Beds | -- Baths | -- Sqft
30 Dinah Rock Rd, Shelter Island, NY 11964
House For Sale

Built circa 1775 and moved by barge from Cutchogue ,NY to Shelter Island in 1969, waterviews. 3 Bedroom 2 Baths, Livingroom,Diningroom, Kitchen master on first floor, 2 bedrooms on second floor.

$895,000Est. Payment
3 Beds | 2 Baths | 1,496 Sqft
1 Lilliput Lane, Shelter Island, NY 11964
House For Sale

This cozy ranch is ready to move right in. Three bedrooms, two baths and an open floor plan plus a screened-in porch make this an ideal family country home. There's also a full basement, a single-car garage and room for a pool. Set in desirable Silver Beach, closeto the Association beach or bike to Shell Beach or Crescent Beach. A rare buy for under a million. Taxes: $3,658.65 Please call M. Wein Realty, Inc. 631-749-0999

$700,000Est. Payment
1.96 Acres
18 Country Club Drive, Shelter Island, NY 11964
Lots Land For Sale

Incredible opportunity to own 1.96 Acres abbuting Gardiners Bay Country Club in the Hay Beach section of Shelter Island. Build your dream home on this large, private lot, with many mature oak trees for added character. Ample of room for a large custom home with tennis court, pool, etc. Once in a lifetime opportunity for a lot of this size in an extremely desireable location.

$1,950,000Est. Payment
1.56 Acres
47 Shore Road, Shelter Island, NY 11964
Lots Land For Sale

Incredible bay-front panoramas from this elevated bluff above Shelter Island's Crescent Beach. A truly amazing location for your island dream home. Private, spacious & elegant, this setting is incomparable & very rarely available.

$2,390,000Est. Payment
3 Beds | 3 Baths | 1,544 Sqft
87 N Ferry Road, Shelter Island, NY 11965
House For Sale

Incredible Business Opportunity on 1.62 Acres. This centrally located fully operational restaurant accommodates 56 seats, has a market, takeout counter, main dining room, covered porch, outside eating area and spacious commercial kitchen. A country farm stand provides a space for pop-up summer markets . The lager 2550 sqft. workshop creates plenty of options for any entrepreneurial spirit. The farmhouse with 3 bedrooms and 2 Baths makes for the ideal live and work lifestyle .

$1,150,000Est. Payment
4 Acres
29 St Marys Road, Shelter Island, NY 11964
Lots Land For Sale

Lovely flat 4 acre property. Level and partially cleared. Partially wooded at one time in cultivation with nursery stock. Mature nursery stock still exists on Southern half of property. Conservation easement on 2 of the 4 total acres. The Northerly 50% of property can be developed residentially with 2 building lots. Bounded on the West side by 24 acre preserve. Property has been removed of buildings, cesspools and fuel tanks

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