Shelter Island Houses for Sale

Around the bend from Turkem's Rest and a short paddle from Salt and Shipwreck, this recently renovated, 4-bedroom, circa 1908 Shelter Island farmhouse, on a shy acre, is perched above Menantic Creek with a substantial dock and profits from panoramic water views with southwestern exposure for magical sunsets. Wide waterfront vistas unfold across beautiful landscaping by Marders, broad greens lined

Shane Donahue The Agency Hamptons

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

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

Shelter Island Sound water front beach house offers stunning sunsets, sandy beach, fully bulkheaded, L'Shaped dock with lift and splash boards;a waterside 50' heated Gunite pool; and expansive unobstructed views out to Robins Island. A serene retreat with a blend of comfort and coastal charm nestled on .75 acres. Designed for relaxation as well as easy entertaining, with a straightforward layout

Melina Wein M WEIN REALTY INC

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

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

Nestled off the road for added privacy this updated home offers Chase Creek water views. Featuring 2 bedrooms and 2 renovated bathrooms, the layout includes an office perfect for remote work or creative pursuits. The open-concept living and dining area is bright and inviting, flowing into the renovated kitchen with modern finishes and storage. Step out onto the back deck thru sliders from the

Melina Wein M WEIN REALTY INC

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

6 Bedroom 6 Bath residence nestled in the heart of historic Shelter Island Heights.Over 5000 sq ft of living spaceGunite Heated PoolExtensive ipe decking on main house and guest house apartment Brand New Kitchen with Monogram appliancesPrivate Beach Club Immediate occupancy available Being sold furnished

Joseph Johns Joseph W Johns

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

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

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

Tucked away on a shy acre, this private retreat features a heated Gunite pool, fire-pit seating area, all framed by mature trees. The main house has an open floor plan with cathedral ceilings and exposed wood beams in the living room, a cook's kitchen with stainless steel appliances, island seating for 3-4, and a dining area that flows easily for entertaining. A deck off the kitchen sets the

Melina Wein M WEIN REALTY INC

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 recently renovated 3 bedroom, two bath home with wood burning fireplace is situated on .89 private acres. The home now has a: new roof, siding, and air conditioners. Newly refinished floors, painted interior, new back decks, exterior basement entry and new appliances. Turn key and ready for you to enjoy for Summer 2025.

Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

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 unparalleled privacy and serenity within the heart of the 2,350-acre Mashomack Nature Preserve, a rare and cherished enclave. At the culmination of a secluded, winding drive, this newly constructed architectural gem unveils itself, a testament to modern design and uncompromising quality. Spanning 3,800 square feet, this residence is a symphony of light and space, framed by walls of glass

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

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

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. The expansive living areas are elegant and spacious, offering ideal settings for both relaxation and

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

Quintessential Hamptons estate in the heart of Shelter Island . Enjoy the best of both worlds at this traditional Hamptons style home, with approximately 5000sqft of immaculate living space across one level, and nearly an acre of land, it's the perfect setting for the best of year round and seamless indoor-outdoor living. The custom-built home welcomes you with its vaulted ceiling in the foyer,

Adam Hofer Douglas Elliman Real Estate

Located just a seven minute walk from the North Ferry, this delightful 4-bedroom, 2.5-bath cottage blends charm with convenience. The home features an open kitchen and dining area, a cozy living room, a media room, and a patio with an outdoor shower and BBQ. The beautifully landscaped yard and garden offer a peaceful retreat, with space to add a pool or garage. Zoned for business, this property

Scott Murphy Saunders & Associates

Introducing an extraordinary new construction completed in 2024, nestled in the Historic Business District of Shelter Island Heights. Allowing for both residential and commercial uses, the offering was constructed in a traditional Heights vernacular with all modern amenities, seamlessly integrating historic charm with functionality. The main building, currently permitted as a primary residence

Hedgerow Exclusive Team Hedgerow Exclusive Properties

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

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

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

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

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

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