Shelter Island NY Real Estate & Homes for Sale

HARBOR VIEW ESTATES: Private community with deeded beach rights. Three to four bedrooms, two baths, study, fireplace, living room, open kitchen, full basement, decks, heated gunite swimming pool, detached two garage garage. Exclusive: $1.585M. Please call Angelo at Dering Harbor Real Estate.

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.

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.

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.

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.

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.

Situated in a quiet neighborhood, just a 5 minute walk from West Neck Bay, and Bootlegger Alley Beach. This brand new 4 bedroom, 4.5 bath room home is currently under construction for summer 2024! Designed and built by Award winning Hamptons Architectural Firm London Architecture + Design. The home features 4 ensuite bedrooms with room for King-sized beds. The open floor plans includes a custom modern European kitchen with LP gas range and 8' island facing a dining and living room with wood burning fireplace. A wall of 8' tall glass sliding doors open up to an expansive mahogany deck and in-ground pool. The lower level is finished with 9' ceilings and glass sliding doors opening up to an areaway and OSE with lots of natural light. A seperate garage with aluminum and glass door can easily double as a pool cabana if you so wish. Finished with wide plank white oak floors, Andersen Windows, Fiber Cement and Mahogany siding. This stunning home will sell fast!

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 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.

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.

Modern luxury meets tranquility in Hay Beach. This exceptional 3-bedroom, 3-bath Modern Ranch nestled in Hay Beach's wooded haven offers an escape from the ordinary. Step inside and be greeted by an open floor plan, seamlessly connecting the living room, dining area, and a chef's dream kitchen. High-end appliances from Bosch, Liebherr, and Viking shine within custom Levante wood cabinetry and granite countertops. Unwind in Your Private Backyard Paradise. Be captivated by the home's breathtaking gardens surrounding the inviting in-ground pool and hot tub. This fully renovated, turnkey oasis awaits you - move in and start relaxing today!

Modern luxury meets tranquility in Hay Beach. This exceptional 3-bedroom, 3-bath Modern Ranch nestled in Hay Beach's wooded haven offers an escape from the ordinary. Step inside and be greeted by an open floor plan, seamlessly connecting the living room, dining area, and a chef's dream kitchen. High-end appliances from Bosch, Liebherr, and Viking shine within custom Levante wood cabinetry and granite countertops. Unwind in Your Private Backyard Paradise. Be captivated by the home's breathtaking gardens surrounding the inviting in-ground pool and hot tub. This fully renovated, turnkey oasis awaits you - move in and start relaxing today!

Opportunity abounds in this new waterfront Exclusive listing. Beautifully situated on six acres with 349 feet on the shores of Dennis Creek and Coecles Harbor. An authentic 1900 Shelter Island Cape with three bedrooms and 2 baths, living room with fireplace, formal dining room and screened-in porch. Separate garage with extra storage. Tennis court. Endless possibilities for expansion, pool, dock and more. Exclusively listed, priced to sell. Call for details and an appointment. Heat: Oil/Hot Water, Taxes: $14,550.26 Please see the virtual tour.