Shelter Island, NY Homes for Sale with Pool

Enviably located on Shelter Island's southern coast with 113' of waterfront on Menantic Creek, this half-acre property was fully reimagined in a high-end 2017 renovation that left no detail overlooked. Offering 3,676 +/- sq. ft. across 2 levels, the home includes 4 bedrooms, 5 baths, 2 fireplaces, a heated gunite pool, outdoor kitchen, firepit, specimen gardens, and a private deep-water dock. A

Stacey Cohen Saunders & Associates

Welcome 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, thoughtfully paired with today's comforts: central air,

Carl Gambino Compass

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

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

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

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

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

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

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