ML# :3543543   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 coffee or hosting unforgettable gatherings, this waterfront oasis provides the perfect backdrop for every occasion. Don’t miss this opportunity to own a piece of paradise in Mashomack Preserve.

ML# :842082   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 and inviting ambiance. The gourmet kitchen is equipped with high-end appliances, and a granite island seating 10, a spacious breakfast/bar with ample counter space, perfect for cooking and entertaining. A large adjacent sunroom, with double doors opening to beautifully landscaped gardens and a patio, provides an ideal setting for gatherings or quiet relaxation. The first floor boasts a luxurious primary suite with custom-built storage, two walk-in closets, and a spacious en-suite bath with a dedicated vanity area. A second bedroom, a full bath, and a versatile art studio with skylights—also with double doors leading to the patio—complete the main level. Upstairs, you’ll find an additional large bedroom, and a 12’x30’ framed out space for a theater, office, gym, game room, or whatever you desire. The home also includes a generous two-car garage, ensuring ample space for vehicles and equipment, a whole house generator, 1000 gallon propane tank, and radiant heat flooring. With its thoughtful design, high-quality finishes, and prime location near sought-after beaches and golf courses, this exceptional home is a must-see.

ML# :905186   Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the kitchen-perfect for relaxing or entertaining. There’s plenty of potential here to update or expand with your own design vision. The property also includes a separate, partially completed renovated 1-bedroom cottage, complete with a legal kitchen, spacious bathroom, and inviting living area-ideal for guests, extended family, or as a rental income opportunity. A detached 2-car garage and ample outdoor space, including room for a pool, complete this rare offering in one of the area’s most desirable locations. Owned solar panels provide significant energy savings with little to no ongoing cost. Don’t miss your chance to enjoy the peaceful living just minutes from local favorites and the charm of the surrounding community. The sauna, lap pool, and generator in the basement are not being represented. This home is being sold As Is

ML# :901615   This enchanting Shelter Island home feels like a true getaway. Tucked into a peaceful setting, it offers a sense of calm and ease the moment you arrive. The house has a warm and welcoming atmosphere, with open, airy spaces that invite you to slow down and unwind. A large living room and kitchen create the heart of the home, centered by a wood-burning fireplace - perfect for gathering with friends or family. Cozy bedrooms provide comfort and privacy, while the flow of the house makes it easy to host and enjoy time together. With a separate entrance to the upstairs, this additional living space offers rental opportunity or dual living accommodation. With its retreat-like atmosphere and charming character, this home is a place to relax, recharge, and enjoy all that Shelter Island has to offer. Some highlights include new appliances, a new water filtration system, beautiful landscaping, and room for a pool!

ML# :901821   Nestled on a serene .58-acre parcel just minutes from Wades Beach and Fresh Pond, this well-maintained ranch-style home offers the perfect blend of classic Shelter Island charm and modern convenience. Built in 1967 and lovingly cared for, the home features 1, 340 square feet of single-level living with 3 bedrooms and 2 full baths, including a primary en-suite for added comfort and privacy.The light-filled interior boasts a thoughtful layout, complemented by a hall bath tastefully renovated in 2021. The property also includes a full basement, partially finished, offering flexible space for storage, recreation, or hobbies.Energy-conscious buyers will appreciate the owned solar panels, reducing utility costs and enhancing sustainability. In the expansive backyard, you’ll find a versatile barn built in 2006, complete with a wood shop on the first floor and a spacious second-floor storage area. While the barn is equipped with propane heat, there is no running water.Whether you’re looking for a full-time home, a weekend getaway, or a place with space to create, this Shelter Island spot has it all-great location, charm, and room to make it your own, just minutes from the beach and peaceful island surroundings.

ML# :889684   Design Your Luxury Island Estate.Seize the rare opportunity to create your custom dream home on this pristine, level lot nestled in one of Shelter Island’s most desirable locations. Moments from the serene shores of Crescent Beach and the tranquil waters of Wades Beach, this property offers both privacy and proximity to the best of island living.Enjoy effortless access to Sunset Beach’s vibrant waterfront dining, the Shelter Island Yacht Club, and charming boutiques in the village. Whether you envision a sophisticated summer retreat or a year-round sanctuary, this parcel offers the canvas to build a legacy home tailored to your lifestyle.The seller will provide Suffolk County Board of Health (SCBoH) approval for the sanitary system. Building permits are required—please consult with the Town of Shelter Island for guidance specific to your plans.A motivated seller invites serious inquiries—build your legacy on Shelter Island.