Shelter Island, NY Homes for Sale with Garage

A rare offering on Shelter Island, this waterfront estate represents a legacy of architectural pedigree and enduring luxury. Built in 1860 and renovated over the years, the home is a singular blend of history and Hamptons elegance, set on nearly 3 acres with western-facing water views, a deepwater dock, and every hallmark of refined coastal living. In an iconic Shelter Island location on West

Myles Reilly Saunders & Associates

A buyers dream rooted in nature, enhanced by design. This modern farmhouse nestled in the heart of Shelter Island, NY. completed in 2024, sits on a generous 2.16 acres of immaculate grounds, is a mere half mile from the South Ferry, placing convenience at your doorstep.Boasting six bedrooms, each with their own en-suite, and two additional half-baths, this residence effortlessly blends style and

Christine Beckwith Douglas Elliman Real Estate

Shelter Island Sound water front beach house offers stunning sunsets, sandy beach, fully bulkheaded, L'Shaped dock with lift and splash boards;a waterside 50' heated Gunite pool; and expansive unobstructed views out to Robins Island. A serene retreat with a blend of comfort and coastal charm nestled on .75 acres. Designed for relaxation as well as easy entertaining, with a straightforward layout

Melina Wein M WEIN REALTY INC

Escape to tranquility in this shingle-style waterfront home, perfectly situated on 1.16 acres of mature plantings with 155 feet of pristine beach frontage. Enjoy breathtakingwater views from nearly every room, where nature's beauty meets relaxedliving. The main house features 4 spacious bedrooms and baths, Livingroom with build-in's, Cathedral ceiling and a wall of glass windows and doors leading

Melina Wein M WEIN REALTY INC

Infinite Views over Shelter Island Sound and extensive bulk-headed sandy beach front make for perfect, summer days and sunset filled nights spent enjoying the beauty and tranquility of this property. Charming interior with beautiful wood floors and touches of wainscoting, living room with beamed cathedral ceiling, picture window and wood burning fireplace, cooks kitchen with dining alcove, two

Melina Wein M WEIN REALTY INC

Surprisingly larger than it looks! Value, Location and Style adorn this Rare Sunset 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

Susan Cincotta Susan C Cincotta

Tucked away on a shy acre, this private retreat features a heated Gunite pool, fire-pit seating area, all 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

Melina Wein M WEIN REALTY INC

Nestled in the desirable and tranquil Hay Beach neighborhood, this elegant custom home was lovingly crafted by a local artist in 2011 and spans 3,170 square feet. Designed to maximize natural light, the residence offers a seamless blend of craftsmanship, comfort, and modern convenience. The home features 21' vaulted ceilings, radiant floor heating, and a striking stone fireplace, creating a warm

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

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

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

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

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. LOCATED IN "C" ZONE: GREAT OPPORTUNITY FOR

Angelo Piccozzi DERING HARBOR REAL ESTATE LLC