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

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 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

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

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

Originally conceived as the Laguna Project, 9 Margarets Drive is an AIA Award-winning residence where architecture, landscape, and natural light exist in 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, thoughtfully composed to create a seamless connection between

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