Shelter Island, NY Homes for Sale

Tucked away on a shy acre, this private retreat features a heated Gunite pool framed by mature trees. The main house has an open floor plan with cathedral ceilings and exposed wood beams in the living room, a cook's kitchen with stainless steel appliances, island seating for 3-4, and a dining area that flows easily for entertaining. A deck off the kitchen sets the stage for alfresco dining and

Melina Wein M WEIN REALTY INC

Nestled on over an acre along Shelter Island's coveted Dickerson Creek, this Scandinavian-style waterfront cottage offers a serene escape with 100 feet of gorgeous shoreline. Imagine waking up to breathtaking sunrises and launching your paddleboard right from your backyard!Inside, discover a light-filled comfortable floor plan enhanced by Swedish-inspired decor. The home features three bedrooms

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

This exceptional south-facing two-story home is nestled on 3.44 acres, offering breathtaking panoramic views of lush lawns, towering mature trees, a serene pond, and a charming barn. The front yard features a circular driveway and a double-arched covered porch with a beautiful bluestone patio. Inside, the entryway leads into a bright dining room and a spacious living room, both adorned with

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

Value, Location and Style adorn this Rare Waterfront Green Lawns Gem on gorgeous Shelter Island. Available after 100 years of property ownership. The 190' of Silver Beach waterfront is fully bulk headed with dock on a level acre with generous side lawn. Perfect for entertaining or escaping as it's surrounded by mature landscaping. Reich Eklund custom built this jewel of a beach house in 1985 and

Susan Cincotta Susan C Cincotta

Quintessential Hamptons estate in the heart of Shelter Island . Enjoy the best of both worlds at this traditional Hamptons style home, with approximately 5000sqft of immaculate living space across one level, and nearly an acre of land, it's the perfect setting for the best of year round and seamless indoor-outdoor living. The custom-built home welcomes you with its vaulted ceiling in the foyer,

Adam Hofer Douglas Elliman Real Estate

Surrounded by preserved land this classic home has an absolutely magnificent setting that includes stunning water views. The open kitchen, breakfast room and family room creates a comfortable bright living area that walks out to a lovely patio overlooking Gardiners Bay . The more formal dining and living room with fireplace also provides amazing views of the water. The spacious primary bedroom

Mary Elizabeth Galle Corcoran

Discover a secluded paradise on Shelter Island, nestled within the expansive 2,350-acre Mashomack Nature Preserve. Tucked away at the end of a private road lies a unique opportunity: 1.74 acres of picturesque land featuring a charming 1,800 square-foot home with three bedrooms. Enjoy breathtaking water vistas from every window, 150 feet of direct water frontage, and the convenience of a private

Hedgerow Exclusive Team Hedgerow Exclusive Properties

Picture a rural drive through farm fields and vineyards to a short ferry boat ride from Greenport's harbor, then a scenic meander along Shelter Island's picturesque coves. Continue passing through a golf course and arrive at your home in Hay Beach, across the street from a sandy shoreline with a magnificent sunset and bay views directly in front of your home. This could be you this year. The 1900

Caroline Sarraf Compass

Nestled in the desirable and tranquil Hay Beach neighborhood, this elegant Traditional home was lovingly crafted by a local artist in 2011. Spanning 3,170 square feet, the residence offers a seamless blend of craftsmanship, comfort, and modern convenience. Designed to maximize natural light, the home features vaulted ceilings, radiant floor heating, and a striking stone fireplace, creating a warm

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

This recently renovated 3 bedroom, two bath home with wood burning fireplace is situated on .89 private acres. The home now has a: new roof, siding, and air conditioners. Newly refinished floors, painted interior, new back decks, exterior basement entry and new appliances. Turn key and ready for you to enjoy for Summer 2025.

Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

This modern architectual jewel,was desiged by the famed architect William Pedersen, who was the founding design partner of Kohn Pedersen Fox Associates (KPF). The home, studio and garage are situated on 1.3 private acres with specimen trees. Close to Coecles Harbor, nature preserves, and sandy beaches.

Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

Discover unparalleled privacy and serenity within the heart of the 2,350-acre Mashomack Nature Preserve, a rare and cherished enclave. At the culmination of a secluded, winding drive, this newly constructed architectural gem unveils itself, a testament to modern design and uncompromising quality. Spanning 3,800 square feet, this residence is a symphony of light and space, framed by walls of glass

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

Discover this exceptional 5.5-acre estate on Shelter Island, tucked away at the end of a private, tree-lined driveway. A true sanctuary, this property offers breathtaking views, rolling lawns, and lush gardens surrounding a serene, self-sustaining man-made pond. An elevated in-ground infinity pool overlooks the expansive grounds and shimmering pond, creating a stunning retreat. Conveniently

Jessica Von Hagn Compass

Every once in a while a very extraordinary property becomes available. Fox Hollow Farm, a private 7-acre horse farm located at 79 North Midway Road, is one of those. It is truly a property for all seasons. One of only a handful of true horse farms on Shelter Island, the offering includes a stately and restored 6,500 square foot main house, dating back to the 19th century; a detached 3-bay garage;

Nick Gavin Compass

SILVER BEACH WATER VIEWS: This lovely modern sits on an elevated 1.04 acres with water views of Crab Creek and Peconic Bay. The home has 3 bedrooms, 2 baths, wood burning fireplace, chef's kitchen with quartz counter tops, one car garage, wrap around decks, a 40' x 14' heated gunite swimming pool, and outdoor shower. A stone's throw from the 13 acre "Crab Creek Nature Preserve", and the

Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

One Pandion is a truly exceptional and rare offering. Nowhere else on the East End will you find 3.4 acres on the water with a newly completed thoughtfully designed modern home compound with sweeping panoramic views over Coecles Harbor extending to Gardiners Bay and the distant Atlantic Ocean. Masterfully curated by CTLA Design, David Neff Architecture and Curate | Build, this premium built new

Terry Cohen Team Hedgerow Exclusive Properties

At the end of a quiet lane, this contemporary home offers the ultimate in privacy and serenity. Located a short walk to Silver Beach and adjacent to a large county land preserve, the house is situated on 1.5 manicured acres of specimen trees and gardens with winding flagstone paths. Enjoy year round picturesque water views of Crab Creek and Peconic Bay from the house windows, the freeform gunite

John Catrambone DERING HARBOR REAL ESTATE LLC

Step into a piece of history with this beautifully restored Tudor home, originally built in 1901. Meticulously maintained and updated with modern amenities, this 6-bedroom, 4.5-bathroom residence offers the perfect blend of classic charm and contemporary comfort. Inside, you'll find 6 stunning fireplaces, each equipped with heatilators for efficient warmth. The original plaster has been carefully

Linda Mccarthy Daniel Gale Sothebys Intl Rlty

Discover a serene sanctuary amidst the natural beauty of Shelter Island. This stunning residence offers breathtaking water views of Miss Annie's Creek, providing an unparalleled escape from the ordinary. Step onto the property and be captivated by the charm of covered porches and a heated pool, inviting you to relax and soak in the picturesque vistas. Whether you're enjoying a quiet morning

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

Water view second floor condo. Open concept living, with two rooms. Stepping over the threshold into the first room one finds a bathroom to the right with double sinks and full closet. The second room with water views serves as a living, dining room with kitchenette. A slider opens onto a private balcony overlooking Dering and Greenport Harbors. Space for a table with chairs. Unit has designated

Melina Wein M WEIN REALTY INC

This private, gently rolling and wooded 1.16-acre parcel (50,603 sq. ft.) is part of a private four (4) lot residential subdivision called "Stoneleigh." Mature plantings and towering evergreens abound in this estate setting where all four (4) lots are served by an exclusive private road with a stately, pillared entrance. Plentiful potable water is available. Utilities in place include

Christopher Read READ CHRISTOPHER M

Amazing 1800s house with 3 bedrooms and 2 baths. Perfectly quiet location in Shelter Island! Tennis courts directly across the street and backyard view of rolling land, minutes to the beach and a few steps to restaurants and gallery.

Simon Harrison Simon Harrison Real Estate

Convenient to all at 28 Smith Street. The address was originally owned by the Smith family, and it's newly built, well considered, expanded and very charming with three bedrooms 2 full baths and room for a pool on a centrally located corner lot.

Simon Harrison Simon Harrison Real Estate

Hidden away off a private drive this lovely two bedroom and one bath cottage is situated on a full acre of land. The home has an open floor plan with a chef's kitchen, large living room with vaulted ceiling and wood stove. Hardwood floors and tile bathroom. Plus, there is a 60'x 30' storage/ garage with three car/truck bays and work area. Exclusive: $1.15M.

Angelo Piccozzi DERING HARBOR REAL ESTATE LLC