Shelter Island, NY Homes for Sale with Acreage

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

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

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

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

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

Around the bend from Turkem's Rest Trail, on a particularly scenic stretch of South Midway, a long drive leads to a charming and lovingly maintained two bedroom Shelter Island summer cottage, circa 1950, set on a deep 1.18 acre flag lot. The cottage opens with a living room with ample fenestration for delightful afternoon light. The bright eat-in kitchen has an adjacent dining area, awash with

Shane Donahue The Agency Hamptons

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

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

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

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

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