Shelter Island, NY Homes for Sale with Pool

Nestled on a 1.08 acre lot along Shelter Island’s coveted Dickerson Creek, this Scandinavian-style waterfront cottage embodies quintessential Hamptons elegance with 100 feet of picturesque shoreline and a sparkling pool.Inside, a light-filled and inviting floor plan features three bedrooms and two newly updated bathrooms, designed for modern comfort. The stylishly renovated kitchen is sure to

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

Welcome to 55 Peconic Avenue, a bold, newly built statement home completed in 2022 and set on an expansive 1.4-acre parcel in one of Shelter Island's most coveted locations. Designed for true year-round living, this residence captures southwest-facing water views, dramatic light, and a seamless indoor-outdoor lifestyle that today's buyers demand. The main level delivers a clean, open-concept

Jack Richardson SERHANT.

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

Presenting a rare and compelling joint offering at 55 & 70 Peconic Avenue-a modern compound opportunity in one of Shelter Island's most coveted waterfront enclaves. Together, these two distinct yet complementary properties deliver scale, privacy, and irreplaceable southwest-facing water views across the Peconic toward Southampton-creating a legacy estate unlike anything else on the market. 55

Jack Richardson SERHANT.

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

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

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

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