Shelter Island, NY Homes for Sale

Charming cottage-style home offering 3 bedrooms and 2 full baths in a highly desirable central location. Just moments from beautiful beaches, local restaurants, and boutique shops, this inviting property blends classic charm with modern updates. Renovated in 2019 with additional recent improvements, the home features comfortable living spaces filled with warmth and character. Outside, enjoy a

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

This lovely home is nicely sited ona shy acre close to Menhaden LaneBeach and Golf. Hard wood floors throughout.Spaciousliving room with cathedral ceiling, fireplace andsliders which open onto a large deck and yard beyond. Three nice sized bedrooms, two full baths, formal dining room, chef's kitchen with gas stove, Den/potential media roomwith egress, two-car garage+.Yard is fenced with plenty of

Melina Wein M WEIN REALTY INC

Nestled on approximately 2.1 acres with an impressive 186 feet of natural beachfront, 33 Dinah Rock Road is a rare west facing waterfront estate on Shelter Island. This elevated property, rising about 26 feet above sea level, delivers uninterrupted sunset views, refreshing southwest summer breezes, and sweeping vistas across the water. Its defining feature is the expansive private shoreline,

Hedgerow Exclusive Team Hedgerow Exclusive Properties

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach.Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

Welcome to Shelter Island — a place where time slows down and nature takes center stage. Accessible only by ferry, this rare island community offers a level of peace, privacy, and authenticity that is nearly impossible to find in today’s world. Set on over 2 acres of beautifully engineered rolling landscape, this property has been thoughtfully designed to enhance natural beauty while addressing

Ron Moschetta Keller Williams Realty Greater

Situated in the desirable Sherwood Farms neighborhood, just moments from the private beach and tennis court, this charming shingled home has been fully refreshed and is move in ready. Built in 2005 by renowned Shelter Island builder, George Phriender, it is convenient to the South Ferry as well as south shore restaurants and marinas. Enjoy the peace and quiet of Shelter Island only a few minutes

Kieran Brew SERHANT.

A rare opportunity to own a legacy compound on Shelter Island, this offering brings together three income-producing historic cottages and a separate buildable lot, all just moments from the water. Positioned at 2 Prospect Avenue and 38 Rock Point Road, the properties are offered as one cohesive investment, blending immediate revenue with exceptional future potential. Each of the three cottages

Marco Maida Compass Greater NY LLC

This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail,

Enzo Morabito Douglas Elliman Real Estate

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

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

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

A thoughtfully designed retreat offering peace, privacy, and understated luxury.Tucked away on a private drive in the island's center, you're close enough to bike to all of the island’s beaches or restaurants.The approach sets the tone: a winding drive reveals the house gradually. The home emerges across an expansive lawn, its clean black lines and Anderson windows throughout creating a

JoAnn Wind Daniel Gale Sothebys Intl Rlty

Steeped in history and timeless architectural charm, this rare circa-1872 Gothic Revival cottage is located within the historic district of Shelter Island Heights, listed on both the National and New York State Registers of Historic Places. Beautifully preserved and largely unchanged since its original design, the home is a remarkable example of the picturesque residential style created by

Mackenzie Needham Daniel Gale Sothebys Intl Rlty

A stone's throw from popular Wades Beach this spacious contemporary is situated on an acre of park like grounds. Four bedrooms, three baths. Living room with vaulted ceilings and wood burning fireplace. Chef's kitchen with open floor plan. Lower level walkout with library/family room and wet bar. Large decks overlooking a heated gunite swimming pool with park like grounds. Exclusive: $2.395M

Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

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

Discover effortless living in this beautifully renovated one-bedroom, one bath co-op on Shelter Island. The apartment is set within a serene and private eight-acre community. Thoughtfully updated, the residence features a modern kitchen and bath, with Bosch appliances, including an in-unit washer anddryer for ultimate convenience. The home opens to a private deck-perfectly suited for outdoor

Elizabeth Wohl Brown Harris Stevens Hamptons

Built in 1888 and thoughtfully renovated by acclaimed architect Lee H. Skolnick in 1988, this storied Shelter Island estate represents a rare convergence of architectural pedigree, cultural history, and timeless design. Set on two exquisitely landscaped acres with gardens designed by celebrated landscape designer Jeff Mendoza, the property has long served as a retreat for notable creative

Stacey Cohen The Agency Hamptons

Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtaking views across Mabel’s Creek and the South Fork, with a sandy beach just steps from your door. As a resident of Shorewood Farms, you’ll also enjoy exclusive access to a private association beach and tennis courts, enhancing the

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

Pool Possible- subject to Permits and approvals.

Erica Lancellotti Serhant East End LLC

Welcome to your dream getaway where modern luxury meets laid-back coastal charm. This Newly renovated 4 Bedroom 3.5 Bathroom home offers perfect blend of style & tranquility, just moments from beaches, marinas and all that island has to offer. Designer Kitchen with Quartz countertops. custom soft close cabinetry with center island & high end appliances. Located on first floor Primary Bedroom with

Anthony Guidice RE/MAX Signature Real Estate

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

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

Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

Set on a quiet street in the Montclair Colony section of Shelter Island, this newly renovated four-bedroom, four-bath combines the ease of single-story living with the feel of a private retreat. The turn-key residence is surrounded by mature hedges on a flat, manicured 0.70-acre lot, providing an exceptional setting for an immediate indoor-outdoor lifestyle and seamless entertaining. Inside, the

Matthew Breitenbach Compass

Originally conceived as the Laguna Project, 9 Margarets is an AIA award-winning modern residence on Shelter Island that brings together architecture, light, and exceptional indoor-outdoor living across ~5,530± SF of thoughtfully designed space, including a substantial finished lower level. Offering 4 en-suite bedrooms, 5 full baths, and 1 half bath, the home is defined by vaulted, light-filled

Jennifer Friedberg Compass

This well-maintained, single-level ranch is ideally situated in the desirable Harborview area of Shelter Island, offering association beach access for effortless coastal living. The home features a spacious kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining.A large, inviting living room with a wood-burning

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

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