Shelter Island, accessible only by ferry, offers a unique real estate market. Here is a list of the five most expensive properties currently for sale on the island. The market seems strong with the top home listing for nearly $20 million and the fifth-place home still listing for close to $10 million. Four of the top five properties are located on the water, but the fifth estate is located on farmland.
1.34a North Cartwright Road, Shelter Island | $19,975,000
Nestled on 2.1 acres of secluded land at 34a North Cartwright Road, Shelter Island, this luxurious five-bedroom, 5 bath retreat is situated on a scenic peninsula. The property boasts 443 feet of Coecles Harbor shoreline, offering breathtaking views of the surrounding waters. Crafted in 2014 from New England reclaimed wood, this 4,490-square-foot home features a grand living room with 24-foot ceilings and towering windows that frame the ever-changing harbor views. The Thermador-equipped kitchen is perfect for culinary enthusiasts, with professional-grade appliances and ample space for entertaining. The primary bedroom suite offers harbor views, a spa-like bath, and a private outdoor deck. Two additional guest suites, a charming bunk room, and a 957-square-foot finished boathouse with an additional guest suite, recreation space and library, provide comfortable accommodations for family and friends. An elevator within the boathouse leads to a secure underground garage and a 100-foot boat dock can accommodate up to four boats. Other outdoor highlights include a large porch, stone terrace and pool all overlooking the harbor. With its artful touches and sophisticated comforts, this stunning property is the ultimate retreat for those seeking luxury and tranquility. Penelope Moore of Saunders & Associates has the listing.
2. 8 Little Ram Island Drive, Shelter Island | $15,495,000
Perched on a picturesque peninsula at 8 Little Ram Island Drive, Shelter Island, this breathtaking eight-bedroom, nine-and-a-half-bath estate showcases unparalleled water views and serene natural beauty. After a meticulous search, the owners discovered the perfect haven to build their dream home. With coveted waterfrontage and a private dock with mooring, this property is a boater’s paradise. The 7,146-square-foot residence, designed by esteemed architect James Merrell, features harmonious spaces for relaxation and entertainment, including a living room with soaring 18-foot ceilings, floor-to-ceiling windows and a fireplace. Private bedrooms are nestled at either end of the house, and staff quarters are located in the finished lower level, ensuring tranquility and seclusion. The estate’s 2+ acres of lush landscape, crafted by Chris LaGuardia, features an infinity pool, spa, and expansive lawns. This stunning property offers a blissful backdrop for a variety of activities, perfect for those seeking a peaceful waterfront retreat. Nick Brown of Sotheby’s International Realty represents the property.
3. Undisclosed Address, Shelter Island | $15,495,000
This newly constructed 5,800-square-foot modern masterpiece, built by Fountainhead Construction Inc., boasts 250 feet of sandy beach and incomparable water views. Listing agent Seth Madore of The Corcoran Group describes the property as “a state of the art, modern house with 180 degrees water views from Crab Creek to North Haven point and up great Peconic Bay. All with 250’ of sandy beach!” Walls of glass in the kitchen, dining area, living room and some bedrooms allow enjoying the stunning water views and brilliant sunsets from indoors or you can slip outdoors onto the waterfront patio or terrace. The sleek 5 bedroom, six and two half bath home features sophisticated amenities throughout such as 10-foot doors, a kitchen with custom Cesar Italian cabinets and natural stone countertops, a fireplace, a media room and a heated waterside pool. Set on 2.12 acres, this secluded property offers a welcome opportunity for refined waterfront living.
4. 1 Pandion Road, Shelter Island | $14,950,000
A brand new modern home overlooking Coecles Harbor Marina recently just came to the market, launched by Hedgerow Exclusive Properties. The 6,000-square-foot house sits on 3.4 acres with 240 feet of bulkheaded frontage. The six-bedroom home offers an open floor plan with a gas fireplace in the living room and a custom kitchen, as well as a home office, a mudroom. The first level also includes a junior primary suite. Take the floating staircase to the second floor for a view of the primary suite with its private terrace overlooking the water, a luxurious adjoining bathroom, a walk-in closet and a private office with a sunset deck. In addition to the main residences, a six-bedroom abode with an open floor plan, custom kitchen and home office, there is also an entertainment barn, an outdoor kitchen and covered dining patio, and a large pool with a sun shelf and an inset hot tub. It also comes with use of a deepwater dock and a tennis court for the Pandion estates.
5. 47 South Ferry Road, Shelter Island | $9,900,000
Nestled on 0.91 acres deep within the stunning 2,350-acre Mashomack Nature Preserve, a secluded gem awaits at 47L’ S Ferry Road, Shelter Island. This modern marvel, situated at the end of a private road, boasts unparalleled luxury and attention to detail. With 3,800- square feet of expertly designed living space, the open floor plan effortlessly merges indoor and outdoor living, showcasing breathtaking Coecles Harbor views from every angle. Premium amenities, top-of-the-line appliances, and walls of windows create a truly unique living experience. The expansive outdoor waterfront deck invites seamless transitions between entertaining and communing with nature. The four bedrooms, including two en suites and two with a shared bath, offer ample closet storage. This extraordinary home, surrounded by nature’s splendor, redefines modern luxury and tranquility.
Honorable Mention:
8 Cobbetts Lane, Shelter Island |$9,750,000
A luxurious farm-style estate, Shelter Island Farm, has recently been completed on 2 acres of historic farmland. Developed by Mike and Kerry Gaynor, the 6,000-square-foot property features five bedrooms, four full and two half bathrooms, with modern amenities, including central air conditioning. The property abuts state land and park-like panoramic views can be enjoyed from the roof deck or porch. Other outdoor highlights include an in-ground pool and a two-car detached garage. Shelter Island Farm offers a peaceful retreat with proximity to the island’s natural beauty. It’s a truly unique property and private tours are available to experience the magic of this one-of-a-kind estate.
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