Shelter Island, NY Homes for Sale with Acreage

Perched 59 feet above sea level for commanding views and peace of mind, this exceptional contemporary estate—designed by noted architect Kenton van Boer—rests on 9.4 private acres, of which 2.7 acres are buildable, and offers 561 feet of premier waterfront on Smiths Cove. Sweeping panoramic vistas of the Sound and the tranquil yacht anchorage set the scene for direct beachfront access and creek

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

Welcome to a truly extraordinary waterfront estate where history, elegance, and coastal luxury converge. Set on the coveted Westmoreland Drive, this stunning 1901 Tudor has been masterfully restored - blending old-world charm with modern sophistication. Inside, you'll be transported by original plaster walls and six dramatic fireplaces, thoughtfully paired with today's comforts: central air,

Carl Gambino Compass

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

Christine Beckwith Douglas Elliman Real Estate

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

Size, Location and Style adorn this Rare Sunset Waterfront Green Lawns Gem. Surprisingly Bigger than it looks! Many believe the side lawn a separate lot from the spacious 5 bedroom Beach House on gorgeous Shelter Island. Finally available after a century 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

Susan Cincotta Susan C Cincotta

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

Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

Nestled on a picturesque full-acre lot facing the serene Mashomek Preserve, this stunning 3-bedroom, 4.5-bathroom contemporary home offers the ultimate in modern living. Built in 2021, every inch of this meticulously designed property showcases custom finishes and high-end amenities, such as heated stone floors, making it the perfect blend of luxury and comfort. The spacious bedrooms each feature

Jonathan Minerick HomeCoin.com

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

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