ML# :842673   For the first time in over a century, this extraordinary collection of generationally owned properties is being offered together as a singular and rare opportunity. Nestled along the serene and picturesque Menantic Creek, these three separate parcels combined total 4.9 acres, which have been combined into one sale, presenting an unrivaled waterfront retreat. The Menantic Creek, known as Hurricane Hole for boat protection during storms, offers boating access to both the North and South Forks and a short run to Montauk. For the boating enthusiast, this offering includes a 100-foot stationary dock, complete with a 6-foot-wide walkway with a bench, as well as a 12-foot plastic ramp leading to a 30x6 ft. floating dock with three anchor pilings. Two moorings on the creek are also available, pending reapplication.At the heart of this offering is 15A Menantic Road, a legally designated two-family residence with a breathtaking 3, 944 square feet of meticulously renovated living space. This refined home features five bedrooms, 4 plus 2 1/2 baths, and a 483-square-foot garage, all thoughtfully designed to maximize the stunning creek views. Taxes: $12, 206.00Adjacent to this residence is 15 Menantic Road, a pristine and vacant 1.3-acre parcel, offering endless potential to further enhance this exceptional estate. Taxes: $4, 325.00Completing the trio is 13 Menantic Road, a charming 1930s bungalow with two bedrooms and one bath set on 1.47 acres and a brand new two story 4 bedroom, 2.5 bath home with attached two car garage in the final stages of completion. Taxes: $8, 521.00What truly sets this estate apart is its extraordinary arboretum-like setting, adorned with a curated collection of rare and mature specimen trees, including Copper Beech, Southern Magnolia, White Birch, Monkey Puzzle, Dawn Redwoods, Linden, Osage Orange, Red Japanese Maple, and Dogwood. The natural beauty of this land is simply unparalleled.This is a once-in-a-lifetime opportunity to own a waterfront compound with limitless potential—a legal multi-family residence, a historic bungalow, a new construction home and an untouched parcel—all in one of the most coveted locations. A truly rare find for the discerning buyer seeking exclusivity, natural beauty, and unparalleled waterfront living.

ML# :838795   Discover unparalleled privacy and serenity within the heart of the 2, 350-acre Mashomack Nature Preserve, a rare and cherished enclave. At the culmination of a secluded, winding drive, this newly constructed architectural gem unveils itself, a testament to modern design and uncompromising quality. Spanning 3, 800 square feet, this residence is a symphony of light and space, framed by walls of glass that capture breathtaking, panoramic views of Coecles Harbor from every angle.Immerse yourself in the seamless flow of the open floor plan, where living, dining, and culinary spaces merge effortlessly, all bathed in natural light and framed by the tranquil water views. Step onto the expansive waterfront deck, a natural extension of the living space, and become one with the pristine beauty of the preserve.This home features two luxurious en-suite bedrooms, including a master retreat, and two additional well-appointed bedrooms sharing a stylish bath, each boasting generous closet space. Every detail has been meticulously curated, from the premium amenities to the top-of-the-line appliances, ensuring a lifestyle of effortless elegance. A testament to its exceptional design, this residence is a proud recipient of the prestigious 2024 Sara National Design Award.Enjoy modern comfort with SEER 12+ cooling and a thoughtfully designed interior featuring a combined living/dining room. This is more than a home; it’s a rare opportunity to live in harmony with nature, surrounded by breathtaking beauty and unparalleled exclusivity.

ML# :880611   Waterfront Compound with 2 DocksLocated on one of the most prestigious beaches on all of Shelter Island is this expansive compound with all the amenities one would want. 332 +/- sandy beach and two docks, breathtaking sunset views from all major rooms, 4 lots, including underwater ownership totaling 1.31 acres, multiple waterfront decks, 4 car garage, game room, regulation size indoor racquet ball court, gym, indoor pool and hot tub and media room. This home could be either a wonderful vacation home or a year round home. Stunning sunsets will bring everyone to the bar-b-que.

ML# :811480   Surprisingly larger than it looks! Value, Location and Style adorn this Rare Sunset Waterfront Green Lawns Gem on gorgeous Shelter Island. Available after 100 years of property ownership. The 190’ of Silver Beach waterfront is fully bulk headed with dock on a level acre with generous side lawn. Perfect for entertaining or escaping as it’s surrounded by mature landscaping. Reich Eklund custom built this jewel of a beach house in 1985 and it is well designed and has been maintained by one owner. All rooms have waterviews including main, living , dining and bedrooms have waterviews from 2 or 3 sides all facing the magnificent waterfront sunsets and sea breezes. This Nantucket Shingle Classic with room for pool has 5 waterview bedrooms (2 en suite) 3.5 baths, full waterside balcony, boasts an open floor plan, 2 car attached garage, scullery/laundry room and full basement with poured concrete foundation with outside bilco door entrance. If you are searching for a carefree, relaxing and magical lifestyle on big waterfront. This might very well be it!

ML# :864101   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 and function. The open floor plan is an entertainer’s dream, seamlessly connecting the living, dining, and kitchen areas. The expansive living room showcases large vaulted ceilings with a floor to ceiling doors with transoms, inviting an abundance of natural light into the space, creating a warm and welcoming atmosphere with an indoor outdoor flow.The kitchen is a culinary delight featuring high-end stainless steel appliances, modern shaker style cabinetry, a wet bar, and pantry. The design is thoughtful and efficient, making it the perfect place to prepare meals and entertain guests.The primary suite, located for optimal privacy, is a sanctuary of peace and relaxation. It features a double shower with steam, creating a spa-like experience within your own home. The second-floor hosts three additional en-suite bedrooms, one of which has its own private deck, offering a tranquil space for morning coffee or evening reflection.The lower level presents a TV room and two more en-suite bedrooms, offering flexibility for various lifestyle needs. The property also includes a heated gunite pool, a large tiled patio, and a pickle ball/sport court, promising endless outdoor entertainment.The entire home is unified by stunning white oak flooring and complemented by well-thought-out outdoor landscape lighting, emphasizing the property’s architectural beauty.The community environment is as inviting as the home itself. With easy access to local amenities and the South Ferry, residents can enjoy the best of Shelter Island living but also having the convenience to the “Sag Harbor Village” and “The Hamptons”.Experience the perfect blend of modern luxury and comfort in this well-designed home. No expense was spared in creating this oasis.

ML# :847290   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 the resort feel, the house is equipped with radiant flooring in all rooms and levels, a two story great room with an indoor/outdoor stone fireplace and a Chef’s kitchen with custom-built cabinetry and granite counters. Large sliding doors lead you onto a wrap-around, mahogany deck with views of greenery and a stunning gunite pool. Upon leaving the main house, you will find every car lover’s dream. A large barn style 4-car garage with ample height for additional car lifts. The 2nd floor features a 1 BR, 1 Bath apartment, full kitchen and an open floor plan living room/dining room.

ML# :3592958  

ML# :3577201   Surrounded by preserved land this classic home has an absolutely magnificent setting that includes stunning water views. The open kitchen, breakfast room and family room creates a comfortable bright living area that walks out to a lovely patio overlooking Gardiners Bay . The more formal dining and living room with fireplace also provides amazing views of the water. The spacious primary bedroom with balcony is as dreamy as the view, which is truly incredible. An oversized bath and additional upper-level bedroom complete this private owner’s area. Two main level bedrooms serviced by a full bath will accommodate family and friends beautifully. A two-car garage and studio with a half bath is a great place to set up your game room or home office. A full basement with high ceilings can be finished to incorporate an exercise or workout room. Lush landscaping with charming stone walls on 1.90 acres completes this peaceful location. Finished Square Footage 3420 includes the Studio. Property could accommodate a pool.

ML# :834105   Welcome to this stunning 6-Bedroom, 4-Bath Home with Water Views on Shelter IslandThis expansive 6-bedroom, 4-bathroom home, nestled in one of Shelter Island’s most sought-after locations, offers a perfect blend of luxury and comfort. Featuring a grand primary suite and a versatile junior suite, it’s ideal for both relaxation and hosting guests.The very large dining room is perfect for entertaining, with plenty of space to host family gatherings or dinner parties. French doors off the dining room leads you onto the spacious deck. The chef’s kitchen boasts a Viking stove, ideal for preparing gourmet meals with ease.Enjoy breathtaking water views from multiple rooms, enhancing the home’s serene atmosphere. The property also includes an elevator for easy access to all floors, ensuring convenience and accessibility. Set on over an acre of beautifully landscaped land, the outdoor space offers endless potential for enjoyment and expansion.This is a rare opportunity to own a remarkable home with exceptional amenities in a prime location. Possible mother/daughter with proper permits. A MUST SEE!!!

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.