Shelter Island NY Real Estate & Homes for Sale

Carriage House, an extraordinary Shelter Island waterfront estate. Originally built in 1888, this magnificient home was reimagined, renovated and expanded in 2010. Sited on 1.7 acres overlooking Dering Harbor this treasure features interior and exterior spaces, with views and amenities beyond. Within the over 9000 sq foot interior are 6 en suite bedrooms and 4 additional powder rooms. Both the upper and main level primary bedrooms include expansive closets, fireplaces and private decks. Large living spaces filled with natural light include an expansive eat in kitchen and great room, 2 large living rooms, theater and a fabulous professional bar leading to the wine cellar below. There are 3 additional fireplaces throughout the main living areas of the home Outside there are gorgeous plantings and garden spaces, 166' of deep water dock and 600 feet of private beach with deeded mooring. Multiple upper and lower decks are perfect for sun worshippers and star gazers, after a swim in the gorgeous heated pool overlooking the harbor. The 4 Car garage and substantial dry storage below must be mentioned. This property is an entertainer's dream and Shelter Island is no longer a "best kept secret." Centrally located between North and South forks and less than a 5 minute ferry ride to all the Hamptons and North Fork have to offer.

Wonderful opportunity to create a Beautiful Year-Round or Seasonal Home on sought-after Shelter Island! Renovate to your particular style and desire. The Front of the home is south-facing, sitting high on a hill, off of the main road. The location is ultra-private and tranquil, offering spectacular views of nature and abundant wildlife, while being surrounded by a mix of Hardwood Forest and Wetlands. Across the street is the Mashomack Preserve, a 2,039 Acre Coastal Nature Reserve on an Island with marshes, forest & creeks. This home needs a renovation, but is structurally sound with good bones, a good roof and good windows. Room for a Pool. Currently no heat nor electric. Cash-only deals.

Hot off the press! This absolutely gorgeous custom-built home is finished and ready to enjoy for the season! 4 spacious bedrooms, 3.5 bathrooms, heated 16x32 gunite pool, mahogany decks - an amazing open floor plan. A true showstopper of a chef's kitchen with GE Cafe series appliances will be the envy of all! Two laundry rooms, living room with a gas fireplace, an office or a gym and a full basement with an egress window. Near Crescent Beach, The Pridwin, Sunset Beach, The Perlman Summer Music Program. Incredible attention to detail - this is a must see! Please call for a private appointment!

This home is nestled in the Montclair Colony area, a peninsula community between West Neck and Menantic Creeks. This quiet area is adorned by acres of walkable preserved lands and easy access to creeks, a marina, and restaurants. Features of this beautiful home include a heated in-ground pool, a large great room with a propane fireplace, a living room with a wood stove, an office area, a powder room, a dining room, an eat-in kitchen, and a master bedroom with ensuite bathroom and walk-in closets. Upstairs are 2 large bedrooms with abundant storage, a cedar closet, and a very large full bath. Outside is a semi-enclosed shower (an island necessity) A breezeway connects the home to the 2-car garage This home was purposefully built to look toward the western sky to witness the brilliant sunsets. Just a wonderful year-round home or seasonal rental.

Situated on .87 acres, this Contemporary style home offers vaulted ceilings, wood burning stove, and a sunroom situated off the living room. The sunroom leads to the rear deck and carport. There is a primary ensuite bedroom with a walk-in closet on the first floor. On the second floor is an open loft living area overlooking the living room, and a guest bedroom and bath. The South Ferry Hills Association Beach is located two blocks away. Great home for year-round or seasonal living. Make Shelter Island your home.

Beautifully treed 1.38 Acres ranch-style home and pond. The sun-filled living room is inviting and leads to the kitchen and lovely sunroom/dining area. In addition, this home offers 3 bedrooms a full bath with a shower. The unfinished basement includes utilities and lots of storage with interior access and a bilco door. There is a spacious deck overlooking the yard and pond. A shed in the yard offers outside storage. This home is being sold as is.

Located in beautiful Harborview Acres with beach and mooring rights, this spacious home is situated on a lovely half acre. The property offers an in-ground pool in a private, wooded yard with cabana and bocce court. This 4 bedroom, 3 Bath home has plenty of potential and includes a second-floor bonus room with stone fireplace. First floor living room with stone fireplace. The u-shaped driveway provides ample off-street parking and leads to a single car garage. Harborview acres is a quiet neighborhood, rear of property backs to acres of vacant, wooded land. Close proximity to beaches, boating, and golf. Please see video tour.

Located on navigable West Neck Creek, this 1970s expanded 6 bed, 4.5 bath contemporary home sits on +/-1.05 acres with spectacular water views. Arrive by boat and private dock to an expansive deck leading into a soaring open plan living and kitchen space. There is plenty of accommodation for all to enjoy this stunning setting surrounded by the natural beauty of Shelter Island. The dock area has been seeded with oysters and clams. A light and airy +/- 624 ft bonus room with 19 ft ceiling is located over the 2 car detached garage, providing opportunity for a studio, office or gym. Waiting to be reimagined for today's indoor outdoor lifestyle, this property is being sold as is.

A true oasis in beautiful South Ferry Hills. This 8BR/4.5BA home feature breathtaking Cathedral ceilings, a gorgeous renovated kitchen w/high end appliances & indoor/outdoor speakers leading to a pool w/retractable cover & a hot tub for cool summer nights. In addition to this magnificent home, a private boat slip is included w/lovely views of the South Ferry from the beach. The paved driveway features a basketball hoop & the yard is spacious for varied lawn games. A truly remarkable home for entertaining w/numerous amenities.

All offers in writing and must include proof of funds, pre-qualification of applicable & corporate documents (if corporate buyer).