Shelter Island Heights, 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

Waterfront Compound with 2 DocksLocated on one of the most prestigious beaches on all of Shelter Island is this expansive compound with all the amenities one would want. 332 +/- sandy beach and two docks, breathtaking sunset views from all major rooms, 4 lots, including underwater ownership totaling 1.31 acres, multiple waterfront decks, 4 car garage, game room, regulation size indoor racquet

Beth Marano Corcoran

Welcome to this exceptional custom-built home nestled on 1.1 secluded acres, offering the perfect blend of luxury, comfort and privacy. Hidden at the end of a long driveway, the main house boasts 3 bedrooms and 3.5 bathrooms. The 1st floor main suite features include double doors that open to a private deck, a WIC and an expansive master bathroom equipped with a spa style rain shower. To add to

Annmarie Seddio Atlas Sales Realty

Sited on one of the highest elevations in Shelter Island Heights & within easy reach of the island's most coveted points of interest, this exquisitely imagined 4-bedroom, 4.5-bathroom brand-new residence on 2 quiet acres offers resort-style luxury living in an oasis of masterful design. A creation of WE+ Architecture & Design, anticipated completion July 2025. The expansive living areas are

Jeremy Dunham Compass

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

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

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

For the first time in over a century, this extraordinary collection of generationally owned properties is being offered together as a singular and rare opportunity. Nestled along the serene and picturesque Menantic Creek, these three separate parcels combined total 4.9 acres, which have been combined into one sale, presenting an unrivaled waterfront retreat. The Menantic Creek, known as Hurricane

Paula Quesnel - Jerman Daniel Gale Sothebys Intl Rlty

Sited on one of the highest points on the island, this home offers magnificent panoramic views everywhere you turn. Well-appointed with 4 bedrooms, 3.5 baths, elevator, eat-in chefs kitchen, formal dining room, living room with fireplace. Expansive decks, and heated Gunite pool offer unobstructed water views. Separate Guest house with 2 bedrooms, bath and sitting room. Heat: Oil/Hot Air, SI Town

Melina Wein M WEIN REALTY INC

This architecturally distinctive home, inspired by the mid-century California Case Study Houses and designed by AC Hocek, is set on two acres of gently sloping land in the prestigious estate area, "Greenlawns". Designed with a thoughtful balance of form and function, the property includes a main house and a separate guest house, offering a unique blend of modern design and natural

Penelope Moore SAUNDERS & ASSOCIATES

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

This exquisite, light-filled, four bedroom, three-and-a-half bathroom architecturally designed mid-century modern is sited on two private acres in the Nostrand Estate section of Shelter Island, a short distance to Sunset Beach, Perlman Music Center, and the Pridwin Hotel. The main house offers spectacular open plan living with an expansive great room incorporating generous living (including a

Melina Wein M WEIN REALTY INC

Introducing Aquarelle at 20 Prospect Ave, an iconic piece of Shelter Island Heights history. Built in 1883, this distinguished home holds a cherished place among the original residences in this esteemed neighborhood, now classified as a national historic district. When upon Prospect Avenue, once known as Divinity Hill, you'll find yourself transported to a time when Methodist ministers from New

Hedgerow Exclusive Team Hedgerow Exclusive Properties

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