Shelter Island NY Real Estate & Homes for Sale

Nestled amidst the serene beauty of Shelter Island, this stunning residential home presents an unparalleled opportunity for those seeking a tranquil retreat. Boasting breathtaking water views of Miss Annie's Creek in the renowned Mashomack Preserve, this residence seamlessly blends relaxation with pristine natural surroundings. As you step onto the property, you're greeted by the charm of covered porches, and heated pool, inviting you to unwind and soak in the picturesque vistas that stretch as far as the eye can see. Whether you're savoring your morning coffee or hosting intimate gatherings with loved ones, these serene outdoor spaces provide the perfect backdrop for every occasion.

Cool Modern with 4 bedrooms, 3 baths nestled on Bucolic Fresh Pond with waterside decks from 3 bedrooms including the spacious primary suite. Mature landscaping and lawn down a private driveway. Recently renovated and updated includes solar panels, new decks and IA septic system. The open floor plan has beautiful waterviews.

Discover this custom-built contemporary home nestled on 1.47 acres of serene beauty. Crafted with love, it boasts cedar siding, wide plank pine floors, and hand-hewn timbers. Approach through a meandering driveway, greeted by vibrant gardens and majestic trees-a perfect outdoor oasis. Inside, soak in the timeless charm of pine floors and abundant natural light. A passive solar design ensures energy efficiency. The allure doesn't end there; ascend to the second floor, a canvas awaiting your personal touch. With soaring 14-foot ceilings and Board of Health approval for a total of 4-bedrooms, the possibilities are endless to tailor this space to your unique vision and needs. Convenience meets coastal charm as this property is just moments away from the pristine shores of Crescent Beach, tantalizing restaurants, and eclectic shops.

Sun-drenched living unfolds in this 2.16-acre south-facing haven, where light bathes a charming Hampton's-style shingled home. Relax by the sparkling Gunite pool, accessible through expansive glass doors from the 2-story living room, warmed by the soaring fireplace. Unleash your inner chef in the spacious kitchen, boasting shaker-style white cabinets, gleaming quartz counters, and top-of-the-line stainless steel appliances. The adjoining family room beckons with its cozy gas fireplace and seamless access to the patio, perfect for effortless entertaining. Unwind in one of 6 bedrooms, each offering a peaceful escape. Indulge in self-care in 6 full and 2 half baths. The partially finished lower level presents additional flexibility with 2 bedrooms, 2 baths, and living area, ideal for guests or a media room. The 2-car garage is directly connected to the kitchen. Escape to charming Sag Harbor in mere minutes, with the South Ferry just .5 miles away. Make idyllic Shelter Island your home.

Situated on a shy acre, is a beautiful traditional, Hampton's style shingle home. With over 5000 sq. ft. of living space on mostly one level, this home has it all. The grand foyer welcomes you with vaulted ceilings and opens into the living room with wood burning fireplace. The chef's kitchen offers luxury appliances, large island, granite counters, wet bar and breakfast area. Most rooms lead to the rear courtyard, with patio, wood burning fireplace and heated Gunite pool. The primary bedroom en-suite and the separate guest wing with den and fireplace creates an estate like feeling. This property is centrally located and minutes to beaches, shops, dining, school and ferries to both the Hamptons and the North Fork.

This lovely ranch located in Hay Beach on 1.06 Acres, is in an ideal setting, close to beaches and golf courses. Boasting 3 bedrooms and 2.5 baths, one of which is the primary ensuite bedroom with a walk-in closet, providing comfortable accommodation. This spacious home features an eat-in-kitchen illuminated by a skylight, cathedral / vaulted ceilings, hardwood floors, a pantry, and powder room, home office, a formal dining room, and an inviting living room with fireplace, and sliding glass doors leading to an outdoor deck. The outdoor area is perfect for enjoying the serene surroundings. Additionally, there is a full basement, partially finished, and a spacious 2-car garage. With all these amenities and priced to sell this property presents a wonderful opportunity for prospective buyers.

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.

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.

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.

Presenting Shelter Island Farm. Just completed and spread across acres of historic Shelter Island farmland, words cant begin to describe this new construction farm style estate from Wall Street Journal "House Of The Year" developers, Mike & Kerry Gaynor. Come visit Shelter Island, have lunch at one of our many new hotels and restaurants and schedule your private tour of this stunning new estate. There is absolutely nothing else like it anywhere on the market.

Beautifully updated, 3 bedroom, 2 bath one level home. Sited on .5 acres and centrally located on a private road, close to South Ferry. This home offers an open floorplan, refinished wood floors throughout, updated bathrooms and an attached 2 car garage with a fenced yard. The primary bedroom and sunroom lead to a rear deck and yard. In addition, there is a large unfinished basement with garage door entrance and utilities. A wonderful property and close to all.

Shelter Island Heights Waterfront Property ! This contemporary 3-bedroom home with stunning sunset and water views, perched above trees, is fantastic place for someone looking for a serene and picturesque setting. Decks surrounding the living areas providing plenty of outdoor spaces for relaxation and entertainment. The bright and open living room with a fireplace, dining room, and eat-in kitchen not only offer spacious living areas but also encompass spectacular views of Pipers Cove Bay. The premier bedroom suite on the main floor with a balcony offers privacy and a place to unwind while still enjoying the scenic surroundings. The 50 foot shorefront of white sand beach is an oasis. A boat mooring, room for pool, tennis and beach club member add splendid amenities to this package

SHELTER ISLAND COMPOUND WITH ABILITY TO SUBDIVIDE Welcome to a haven of natural beauty with limitless opportunities. This meticulously crafted Shelter Island 8.45acre estate property is currently configured with 3 substantial structures: a 3Bed/4Bath primary residence, a 2-car carriage house with loft apartment and a 3 stall horse barn with tack room and loft space. This is a rare opportunity to live your equestrian dreams OR IF YOU'RE NOT A HORSE ENTHUSIAST, this C-Zone property can be reimagined as your own sprawling compound with commercial/work options or the property can be subdivided into separate parcels. The pastures, paddocks and cedar grove make this a true gem for horse enthusiasts, a family compound with multiple dwelling options or as gym/yoga, art studio or light commercial/work spaces. The centerpiece of this remarkable estate is the main residence, a 3225 square foot country home boasting 3bedrooms and 4 bathrooms. All bedrooms are ensuite and the home also boast formal dining room, entry way, main floor laundry and ample size living/family room. Also on the first floor, the primary suite is equipped with a beautiful sunroom with radiant heat floors. large dressing room, and extra-large ensuite bathroom with soaking tub. The second floor has two ensuite bedrooms and a bonus family/ media room as optional 4th bedroom with high ceilings. The finished expansive lower level with full bath is walk out to the rolling property. Above the two-car garage there is loft apartment space with kitchen and full bathroom. This expansive space also boasts high ceilings and a balcony overlooking the 18x 44 gunite pool with waterfall. In addition, the property has a functional horse barn with 3 stalls tack room and loft space OR reimagine to suit your needs. As a horse farm this expansive Shelter Island property represents a rare opportunity to own a world-class equestrian estate in one of the most beautiful and sought-after locations in the region. Whether you are a seasoned equestrian or simply seeking a serene escape, this property features the perfect blend of luxury, natural beauty, and equestrian excellence. Don't miss your chance to make this dream equestrian retreat your own.

Nestled in the tranquil wooded haven of Hay Beach is this exceptional 3-bedroom 3-bath modern ranch. Upon entering, you are welcomed by an open floor plan that effortlessly connects the living, dining, and kitchen areas. These are rounded off by top-of-the-line appliances from Bosch, Liebherr, and Viking, all set within Levante wood cabinetry and granite countertops. Step outside and be captivated by the breathtaking gardens surrounding the inground pool and hot tub. Escape from the stresses of everyday life. This renovated turnkey oasis awaits you.