Shelter Island, NY Homes for Sale with Garage

A rare turnkey Shelter Island retreat with two distinct homes tucked away on nearly an acre in the heart of Shelter Island, 64A North Midway Road presents a truly unique opportunity to own two homes on one private property. Surrounded by mature trees, expansive lawns, and a picturesque pond next door, this exceptional estate blends privacy, flexibility, and timeless charm. This rare property

Christine Beckwith Douglas Elliman Real Estate

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

Brand new in one of Shelter Island's premier enclaves along Gardiners Bay, this custom 5,535 +/- SF, south-facing residence developed by Juno Homes presents a refined blend of luxury, location, and design. Defined by soaring proportions, sleek attention to detail and bathed in natural light, the home features 5 ensuite bedrooms, 6 full baths and one half bathroom across two levels. Upon entry, a

Kristy Naddell Douglas Elliman Real Estate

Situated in the desirable Shorewood 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.

Set on 1.05± acres along the shores of West Neck Creek, 8 Margaret's Drive presents a newly constructed waterfront residence designed to embrace the natural beauty and relaxed character of Shelter Island. With direct frontage along the creek and a thoughtful orientation toward the water, the property brings together refined new construction, generous outdoor living, and a private waterfront

Hedgerow Exclusive Team Hedgerow Exclusive Properties

Own a distinctive piece of Shelter Island Heights history in this beautifully restored circa-1875 residence, thoughtfully updated for today’s lifestyle while retaining the character and architectural details that make a historic home so special. Set on approximately 0.40 acres, the property offers second-level water views, inviting private gardens, and a classic wraparound porch ideal for

Douglas Cabral Century 21 Excelsior Realty

Shelter Island Heights IconGracefully positioned in the heart of Shelter Island Heights, this timeless residence has been thoughtfully renovated and restored to honor its original character while seamlessly incorporating today's modern comforts. Rich in architectural charm and classic detail, the home offers an elegant blend of historic beauty and refined living. A gracious, oversized covered

Donna Walker Douglas Elliman Real Estate

Rarely available in an enviable location directly across from the water with mooring rights, this new construction home in Dering Harbor delivers the best of Hamptons living on Shelter Island, ready for immediate enjoyment and for generations to come. Built in 2026 and sited on 2.4 acres, the new construction property has 7,300 +/- SF of interior living space (including the finished lower level)

Romaine Gordon Saunders & Associates

Set on 1.06 acres with elevated sunrise vistas, this freshly renovated single-story cottage is fully turn-key. The entry foyer, featuring a powder room and separate laundry room, opens to a bright, vaulted main living space that seamlessly combines living and dining areas, featuring a wood-burning fireplace with raised hearth. Strategically placed windows, including a striking round accent window

Penelope Moore 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

This waterfront is classic Shelter Island. Set on more than half an acre with 153 feet of private, bulkheaded sandy beach, this 1952 cottage keeps its head turned to the water from nearly every room. A fireplace and hardwood floors anchor the living room, the primary suite wakes to the Bay, and a covered waterside patio waits for the long part of the evening. Wooden steps lead down to your own

Melina Wein Compass

There are new homes, and then there is this - a turnkey Bartilucci Construction design-build masterpiece, styled by Heiberg Cummings tucked just outside the heart of Shelter Island Heights. No detail left to chance and no corner cut. What sets this location apart is the rare balance it strikes - total privacy paired with true convenience. The Heights business district, morning coffee, boutique

Sheri Winter Parker Corcoran

Just a stone's throw from popular Wades Beach, this spacious contemporary sits on a beautifully landscaped acre of park-like grounds. The home features four bedrooms and three baths, along with a light-filled living room with vaulted ceilings and a wood-burning fireplace. The chef's kitchen opens seamlessly to the living and dining areas, creating an ideal open-concept floor plan. The lower-level

Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

Shelter Island Waterfront with Dock. A rare opportunity to own waterfront in Silver Beach, one of Shelter Island’s most beautiful and sought-after enclaves. Set directly on the tranquil Silver Beach lagoon, this four-bedroom, 2.5-bath home offers approximately 2,289 square feet on a private .76-acre property with approximately 102 feet of waterfront frontage—all just a five-minute walk to

Matthew Hart World Prop Intl Sea to Sky

A perfect blend of stylish comfort and effortless one-level living, this traditional ranch-style home is a short walk to Silver Beach. Nestled on a quiet street surrounded by a beautifully wooded property with seasonal variety landscaping, this residence offers a private sanctuary designed for year-round relaxation and entertainment. The interior spaces extend beautifully to the outdoors,

John Catrambone DERING HARBOR REAL ESTATE LLC

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

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 along the quiet shoreline of Pipers Cove Bay in Shelter Island Heights, this west-facing waterfront retreat is tucked at the end of a private drive and has been thoughtfully reimagined by Heiberg Cummings, whose signature approach to layered design transforms the home into something both sophisticated and deeply connected to its surroundings. Every room on both levels is oriented toward the

Stacey Cohen The Agency Hamptons

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

AIA Award-winning 9 Margarets Drive is a modern Shelter Island retreat where architecture, landscape, and natural light come together with exceptional clarity. Designed by Lacuna Architecture Atelier, the approximately 5,530-square-foot residence, including a substantial finished lower level, offers four en-suite bedrooms, five full baths, and one half bath, with a design centered on a seamless

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