Shelter Island, NY Homes for Sale with Pool

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

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

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

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

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

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

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

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

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

An AIA Award-winning design by Lacuna Architecture Atelier, 9 Margarets Drive brings architecture, landscape, and natural light into remarkable harmony. Encompassing approximately 5,530 square feet, including a substantial finished lower level, the home offers four en-suite bedrooms, five full baths, and one half bath, with a design that creates a seamless connection between indoors and out. A

Jennifer Friedberg Compass

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