Shelter Island Heights, NY Houses for Sale

A Rare Shelter Island Gem with Timeless SoulWelcome to a truly extraordinary waterfront estate where history, elegance, and coastal luxury converge. Set on the coveted Westmoreland Drive, this stunning 1901 Tudor has been masterfully restored - blending old-world charm with modern sophistication.Inside, you’ll be transported by original plaster walls and six dramatic fireplaces,

Carl Gambino Compass Greater NY LLC

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

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

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

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

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

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

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

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

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

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

Newly and imaginatively staged by Cristiana Mascarenhas in conjunction with the acclaimed Brazilian design and furniture company Espasso, the house exudes a sophisticated yet laid-back Brazilian beach vibe that highlights the beauty and the functionality of D&D Harvey Architects design. Introducing an extraordinary new construction completed in 2024, nestled in the Historic Business District of

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

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