ML# :3585239 2025 Rates: June $30, 000, July $60, 000, July-August $125, 000 and August-Labor Day $65, 000. This stunning two-story home sits on 3.44 acres of beautiful lawns and trees, featuring a circular driveway and a double-arched covered porch with bluestone patio. Inside, the foyer opens to a light filled dining room and great room with 10 foot coffered ceilings, exquisite details, and an elegant chef’s kitchen equipped with Crownpoint custom cabinetry and top -of-the-line Wolf and Sub-Zero appliances. French doors lead to a covered porch overlooking the pool and yard. The second floor has 3 bedrooms each with a private bath and 9 foot ceilings. A separate staircase leads to a den with pull out sofa, wet-bar with ref/freezer and it’s own full bath. Additional features include a Gunite heated pool with electric cover, full house generator, alarm system, and two smart tv’s. This home is close proximity to Wades Beach and Mashomack Preserve.
104 S Ferry Rd, Shelter Island, NY, 11964
ML# :3532284 Nestled on 1.06 acres of serene beauty, this charming ranch-style home offers the perfect blend of comfort and coastal living. Enjoy easy access to pristine beaches, world-class golf courses, and all the amenities Hay Beach has to offer. Inside, you’ll find a spacious and inviting interior with hardwood floors, vaulted ceilings, and a skylight-lit eat-in kitchen. The primary suite features a walk-in closet and a private en-suite bathroom, providing a tranquil retreat. Additional bedrooms, a home office, a formal dining room, and a cozy living room with a fireplace offer ample space for relaxation and entertaining. Step outside to your private outdoor oasis, ideal for enjoying the coastal breeze and entertaining guests. A finished basement and a spacious two-car garage provide plenty of storage and workspace. Don’t miss this opportunity to own a piece of paradise in Hay Beach. Schedule your private showing today!
5 Country Club Drive, Shelter Island, NY, 11964
ML# :3521653 In our beloved 2, 350 acres of Mashomack Nature Preserve, there are a handful of residences. At the end of this long private road through this preserve, one can find this breathtaking newly constructed modern home with no details left behind. This expertly crafted home is loaded with premium amenities, top-of-the-line appliances, and walls of windows overlooking Coecles Harbor, this home has no comparisons. With 3, 800 sq. ft., the home features an open floor plan with sweeping water views from every vantage point, whether dining, cooking, or lounging. Continue entertaining outside on the large outdoor waterfront deck where you become one with nature. The master and one of the guest bedrooms are en-suite, and the 2 additional bedrooms share a bath. All the bedrooms have abundant closet storage.
47L S Ferry Rd, Shelter Island, NY, 11964
ML# :3567654 Step into a piece of history with this beautifully restored Tudor home, originally built in 1901. Meticulously maintained and updated with modern amenities, this 6-bedroom, 4.5-bathroom residence offers the perfect blend of classic charm and contemporary comfort. Inside, you’ll find 6 stunning fireplaces, each equipped with heatilators for efficient warmth. The original plaster has been carefully restored, preserving the home’s historic character. New heating and central air conditioning systems ensure year-round comfort, while additional insulation on the second and third floors provides energy efficiency. A chef’s dream, the kitchen has been completely renovated and features a newly added butler’s pantry. Outside, the property boasts a heated 20x50 Gunite pool and hot tub, perfect for entertaining and relaxation. A classic brick patio complements the elegant surroundings, and a deep water dock accommodates multiple boats, making this the ideal waterfront retreat.
9 & 7 Westmoreland Dr., Shelter Island, NY, 11964
ML# :3565240 Nestled amidst rolling lawns, woods, and a stocked pond, this serene 5.5-acre property offers the ultimate in privacy and tranquility. A 1, 000-foot private driveway leads you to this expansive estate, where endless possibilities await. The property features a spacious artist’s studio with a wall of windows on the first floor and a separate apartment above, providing ample space for both work and living. Enjoy the elegant elevated in-ground pool, offering stunning views of the surrounding natural beauty. Conveniently located less than a mile from South Ferry and a short distance to Wades Beach and Mashomack Preserve, this property offers the perfect blend of seclusion and accessibility.
72 S Ferry Rd, Shelter Island, NY, 11964
ML# :3564455 Experience the epitome of coastal living in this meticulously maintained one-level home, nestled in a charming beach community. Renovated in 2012 by Fokine Construction, this stunning residence offers breathtaking water views of Menantic Creek from nearly every room. Inside, you’ll find an open-concept floor plan featuring a vaulted living room with a cozy fireplace, a dining area, and a custom chef’s kitchen. Step outside onto the waterside deck, adorned with mahogany railings and stainless wire, for a serene outdoor retreat. The primary bedroom is a true oasis, complete with two walk-in closets and a luxurious en-suite bathroom. Enjoy the tranquility of the 1.29-acre shared parcel extending into the creek. This quiet enclave offers the perfect blend of luxury and natural beauty, making it an ideal coastal retreat.
5 Hagar Rd, Shelter Island, NY, 11964
ML# :3563528 Discover this inviting Ranch-style home just blocks from the sandy shores of Bootlegger’s Alley beach and breathtaking sunsets. Inside, you’ll find an open-concept floor plan featuring a country kitchen, dining area, living room, and den, perfect for both everyday living and entertaining guests. Cozy up by the wood-burning fireplace or relax on the spacious deck overlooking serene views and glimpses of Westmoreland Mill Pond. Enjoy refreshing summer days in the Gunite in-ground pool with patio surround. This home offers the perfect combination of comfort and outdoor leisure, making it ideal for enjoying island life.
1 Rebel Rd, Shelter Island, NY, 11964
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.
4 Irene Lane, Shelter Island, NY, 11964
ML# :3523302 The ultimate sunrise and sunset views adorn this special waterfront 3 bedroom home on Mabel’s Creek overlooking Shelter Island Sound and the Shelter Island South Ferry route to and from Sag Harbor’s North Haven. Sit outside and renovated 2 story cottage/beach house getaway with water views from most rooms in the house on a quiet street ending at a private Shorewood Association boat launch access to the Shelter Island Sound. Available when living in Shorewood, are community tennis courts, beach access and boat launches and mooring rights. Take a cruise on your kayak, paddle board or boat directly from your private access onto Mabel’s Creek from the back yard. A private boat dock is also a possibility. This is a one-of-a-kind must see property for the low-key buyer who dreams of bucolic waterfront vistas and color-filled skies each and every morning and evening while enjoying breakfast or dinner on the water facing patio or read a novel while relaxing amidst the water’s waves. Do a cheese tasting at White Oak, bear tasting at thee Shelter island brewery or wine tasting at the many new restaurants on Shelter Island including The Rams Head Inn, Leon1909, The Pridwin Inn, The Chequit, play a round of golf at the Shelter Island Golf Club and Flying Goat Restaurant or watch the sunsets over Crescent Beach at the famous Sunset Beach. So close to Sag Harbor on the South Fork are shops, restaurants and Bay Street Theater while Sagaponack and Bridgehampton have pristine white sand ocean beaches, farmland, Wolffer Estate Stables and Vineyard, and world class private golf courses on the South Fork or head to Greenport via the North Ferry for a day on the North Fork touring over 33 wineries, farm stands, shops and restaurants.
3 Seagull Rd, Shelter Island, NY, 11964
ML# :3566661 Welcome to this stunning Ranch nestled in the serene and sought-after neighborhood of Silver Beach on an impressive .87 acre lot with beach rights. This meticulously maintained residence offers a perfect blend of modern comfort and timeless elegance. Upon entering, you’re greeted by an inviting living room accentuated by gleaming hardwood floors. The spacious living area seamlessly connects to the chef-inspired kitchen, complete with sleek stainless steel appliances, granite countertops, and ample cabinetry - an ideal setting for culinary enthusiasts and entertaining guests. Just off the dining area is a sunken enclosed sun room, insulated for all seasons. This tranquil area provides ample natural light and generous space for another living space or dining area. Two of the exterior walls are made up with floor to ceiling windows. Allowing for one to be completely surrounded by nature. Another key highlight of this home is its captivating outdoor space. The private backyard is perfect for relaxation or gatherings, with a well-manicured garden and a charming lounge area - an ideal spot for al fresco dining or enjoying the picturesque views.
42 Brander Parkway, Shelter Island, NY, 11964