Shelter Island Heights NY Real Estate & Homes for Sale

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

Waterfront Condo in desirable West Dublin with views of Peconic Bay and Shelter Island. This first-floor end unit has hardwood floors throughout updated kitchen and baths and waterside living room with wood burning fireplace. The Grounds include salt water pool, tennis court, pickle ball, bike storage, private sandy beach, and boat slip. Short distance to all Greenport Village has to offer. Easy access to Train, Bus, and Shelter Island ferry.

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.

Charming 3 bedroom 2.5 bath Cape with gated yard and heated pool in the heart of everything the North Fork of Long Island has to offer. Built in 2008, the house was refurbished with all new paint, carpets and appliances. Walk to the Fifth Street Beach and Playground which has BBQs, Picnic Tables, volleyball and basketball court. Make this your forever home or summer getaway where you can come in from NYC by the LIRR and walk with your wheelie right to your home away from home. Can also walk to town, harbor, restaurants and pubs. Stove top has gas for cooking. Huge Master Bedroom upstairs with Bedroom & attached full bath downstairs. Two zone central A/C. Unfinished basement with outside access has washer and dryer along with an extra refrigerator/freezer. The inground heated pool with new liner and pump makes staying at the house more fun than the beach. Summer Rentals fetch $5000 week. Furniture & accessories avail.

Location, Location, Location is what this Greenport two story water view home is all about. Renovations had began but not finished, just waiting for you to make your own!

Nestled among the shores of Pipes Cove, this exquisite bayfront home offers the ultimate beach lifestyle, combining relaxation and panoramic views around Conkling Point over to Shelter Island. Every Wednesday evening, chill out on the waterside patio and watch the Shelter Island sailboat races. Have front row seats to the annual 4th of July Shelter Island fireworks display. If you're an early riser, here you'll be captivated by breathtaking sunrises. Launch kayaks, paddle boards, or even a small sailboat from your own beachfront, and explore the waters at your leisure. The home exudes warmth & character, inviting you to unwind and revel in the simple pleasures of life on the Bay. The open floor plan with living, dining, & kitchen are thoughtfully designed to maximize water views and natural light. The primary suite is on the first level with 2 additional bedrooms & a full bathroom. Upstairs has a loft and unfinished space ready to be built out. All of this, only a 3 minute drive to the coveted Greenport Village.

Nestled in the heart of North Fork Wine Country, in the highly sought after West Dublin neighborhood of Greenport Village, ideally located within mere seconds of the vibrant and dynamic Greenport Village shopping district and the rolling waves of nearby 4th Street Bay Beach is where you will find this one of a kind North Fork gem. Distinguished as one of the very few residences in the Village boasting a refreshing and sunsoaked inground pool, this property offers a summer resort style haven of exclusivity providing both privacy, tranquility and convenience having the vibrant offerings of the Village lifestyle found just outside your front door. Welcome home to a first-floor open floor plan that floods the interior with an abundance of natural light, coupled with beautiful hardwood floors, all enhanced by expansive windows and complemented by the warmth of a gas fireplace. Each floor boasts a generously sized owners bedroom accompanied by a full bathroom, ensuring both luxury and convenience. Ascending to the second floor reveals an additional inviting and spacious owners bedroom, and home office /work space. First floor highlights include the spacious chefs kitchen, adorned with quartz countertops and equipped with stainless steel appliances. This space serves as a culinary haven, which effortlessly connects to the spacious rear deck, creating the ideal setting for seamless indoor-outdoor entertaining. The backyard, is a true outdoor private oasis in itself, complete with beautifully manicured gardens, a spacious and sprawling verdant lawn, outdoor shower and your inground pool wrapped in blue stone sitting center stage all summer long. The ideal investment opportunity to enjoy the luxury and super convenience of this prime location is here. Just outside your door are the boutique shops, delectable restaurants, Mitchell Park with its charming carousel, and the picturesque waterfront all waiting to be explored. For those beach lovers seeking the relaxing waves and comfort of a white sandy beach, this residence is also located just a short stroll to its nearby 4th St bay beach found at the end of the street, complete with BBQ/picnic area, and basketball courts. The proximity to rail, jitney, and ferry stops to Shelter Island and the Hamptons further enhances the accessibility of this exceptional home in it's extraordinary location!

Indulge in modern living with this fully renovated 2-bedroom, 1-bath haven. Step onto hardwood floors and experience the stylish eat-in-kitchen featuring Bosch dishwasher and stainless-steel appliances. Stay comfortable year-round with central A/C and revel in the convenience of a washer/dryer with your home. Adore the open layout as you bask in natural light streaming through new windows. Ample additional storage is accessible via the pulldown attic, making clutter a thing of the past. A true MUST SEE, this gem is strategically located near 5th Street beach, making coastal bliss a daily affair. Enjoy seamless access to transportation with proximity to the bus, LIRR, and ferry. Plus, immerse yourself in the charm of Greenport Village's dining and shopping, completing the perfect picture of your dream home. Don't miss out on the opportunity to make this stunning sanctuary yours!

This one bedroom, second floor apartment in Driftwood Cove is perfect for a hassle free weekend getaway or easy year round living. Close to Greenport Village, Shelter Island Ferry and NYC train and bus stations. Can be rented after 1 year of ownership to year round residents. Maximum 2 person occupancy. Additionally Greenport will be investing in rebuilding the harbor bulkhead. Will not last!

Turn-key mixed use offering in the heart of Greenport Village. This space was completely overhauled in 2017 w/ all new HVAC, plumbing and electric. The property is located in the commercial retail district of the village and offers an array of uses, which include and not limited to accessory apartment, gallery, eating and drinking establishment, studio, event space, dry retail, professional office, etc.. The space is currently set up and CO'd as a restaurant and features a large bar, two bathrooms and an area that would be perfect for an open kitchen on the main floor. The second level is a lounge w/ additional half bathroom offering additional seating and views of Greenport shipyard and Greenport Harbor. The lower level consists a prep area, walk-in fridge, ample space for storage and a majority of the mechanicals. This is an investor opportunity or a great space for an end user operator in an ideal location 1 block from the center of the Village

Don't miss out on this Light-filled 3-bedroom, 2-bath custom built modular home, built in 2020. It offers a superior living experience with its solar-powered, Energy Star, and LEED compliant features. Located across the street from Peconic Bay, it boasts peek-a-boo views of the bay with nearby access points to a kayak launch, and tranquil Pipes Cove. This ranch layout includes an upstairs room that can serve as additional living space or an office, providing privacy from the rest of the house with a walk out veranda. Thoughtful gardens outside the living room blur the lines between indoors and outdoors, enhancing the overall ambiance. Residents can relax on the veranda or in the living room while enjoying the scenic views. Additionally, the property features a two-car garage, suitable for parking or storing water sports equipment, and a full, spacious basement that offers ample storage and potential for additional living space. Take advantage of the nearby attractions of the North Fork, including Shelter Island, beaches, farms, vineyards, and restaurants, all while enjoying the tranquility of a small-town atmosphere. Whether you're looking for a peaceful retreat or an active lifestyle surrounded by nature, this home offers the best of both worlds.

Introducing a modern 2-story residence nestled in the charming village of Greenport. This stunning home boasts elegant hardwood floors that grace both the first and second floors, providing a timeless touch of sophistication. The first floor presents a well-thought-out open concept layout. Featuring an inviting living room that seamlessly connects to the HGTV-style kitchen with a gas range for cooking enthusiasts. Also on the first floor, you'll find one of the two primary suites. Offering a private oasis for the discerning homeowner. The 9-foot-high ceilings on this level create an airy and spacious ambiance. The convenience of a second primary suite on the second floor ensures versatility and privacy. The second floor offers a flexible living space, ideal for various uses, and a dedicated laundry room for convenience. In total, boasting four bedrooms and three and a half baths, providing ample space for you and your guests. This home offers the lifestyle you desire. Impeccably constructed in 2022 by a renowned local builder, this beauty exemplifies craftsmanship and attention to detail throughout. Large windows flood the home with natural sunlight, creating a warm and welcoming atmosphere. The home has a Navien on-demand hot water system, and central air. Could be a strong investment property. Plumbing in order for a potential extra bathroom. Situated just a few blocks away from the vibrant heart of Greenport, you'll be minutes away from renowned restaurants, boutique shops, and the picturesque harbor. Transportation options abound with the Long Island Rail Road, the Hampton Jitney, and the ferry to Shelter Island, all just a short stroll away. This dream home is carefully crafted and waiting for you!

beautiful ,Vibrant Greenport Expansive Heated Pool, private parking,Deeded Boat slip INCLUDED. Can DOCK a 35 or larger foot sail boat . Sweeping views of of the Bay from front to rear of Condo.Wood burning Fireplace, Tennis courts, Water is included, most reasonable.Greenport electric. Trash removal, Snow removal, Grounds upkeep Insurance is included.FOR EXTERIOR OF COMPLEX. Sit and watch the children play at the sandy beach from your beautiful back deck.Barbecue and picnic by the water.Where else can you get a waterfront and a Dock for the low price and taxes. This is a Wonderful way to enjoy nature at its most inviting.Steps from Historic Greenport Village. Dine,shop,dance,antique, Close to Ferrys to Hamptons.Shelter Island,or Connecticut from Orient. less than 2 hours from Manhattan. GREAT.GREAT LOCATION.

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.

A distinctive and stylish offering in the heart of Greenport Village. This 4400 sq. ft. loft features 4 bedrooms across three floors of thoughtfully renovated living space and an adjacent 800 sq. ft. accessory building. Twelve oversized skylights flood the main floor with natural light, illuminating the interior and further highlighting the soaring ceilings. The open floor plan creates an inviting atmosphere and an exceptional entertaining space with a chef's kitchen that connects to a second floor outdoor deck. The third floor features lofted ceilings and a primary bedroom with walk in closet and luxurious full bathroom. The ground level offers the perfect blend of comfort and convenience with two bedrooms, two baths, home gym, den and laundry room. A well appointed courtyard connects the main house to the accessory building. With its unique blend of style, sophistication and functionality, all just a block from Village shops, restaurants, and the waterfront, 511 Carpenter offers an opportunity to embrace the quintessential Greenport lifestyle.

Welcome to this stunning four-bedroom colonial home situated on a spacious one-acre lot. This immaculate property offers a perfect blend of elegance and outdoor living, boasting an inground pool and beach rights for your enjoyment. The exterior of the home is highlighted by a 24" x 36" detached garage with a remarkable 12" high ceiling and clear span framing, providing ample space for parking and storage. Inside, you'll find a seamless flow between the open living and dining room, creating a warm and inviting atmosphere for entertaining guests. The kitchen and family room have been tastefully renovated, featuring modern fixtures and appliances that blend seamlessly with the overall design aesthetic.The home has a Bonus Florida Room! It adds 220 square feet to the home.This room offers a tranquil space to unwind and enjoy the surrounding natural beauty of the property. Step outside onto the mahogany deck, where you can relax and soak up the sunshine or host gatherings with family and friends. The new wood flooring throughout the house adds a touch of sophistication and durability. The finished basement is an added bonus, complete with radiant heat, providing additional space for recreational activities or a home office. Other notable features of this home include a new roof and central air conditioning, ensuring year-round comfort and peace of mind. Located in the quiet community of HOA August Acres, this neighborhood offers a serene environment with abundant wildlife. Don't miss the opportunity to make this exceptional home your own and experience the perfect balance of comfort, style, and natural beauty.

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.

Perched above the water with expansive views of Greenport Harbor and Stirling Basin, 123 Stirling offers modern luxury on one of Greenport Village's most beautiful residential streets. Each unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry, and ground floor maritime space with a half bath. Four blocks from the center of the village's shops, restaurants, and galleries. Great proximity to Jitney and LIRR for easy access to NYC. Unit 10 features two bedrooms, two full baths, and one half-bath. Open-concept kitchen/dining/living room. 539 sq ft maritime space with an additional half bath. Sale is subject to the terms & conditions of an offering plan.

Perched above the water with expansive views of Greenport Harbor and Stirling Basin, 123 Stirling offers modern luxury on one of Greenport Village's most beautiful streets. Each unit includes a private boat slip, dedicated indoor and outdoor parking spaces, in-unit laundry and ground floor maritime space with an additional half bath. Four blocks from the center of the village commercial district with shops, restaurants, and galleries. Great proximity to Jitney and LIRR for easy access to NYC. Unit 2 features three bedrooms, two full baths and one half bath. Open concept kitchen / dining / living room. 500 sq ft maritime space with additional half bath and 224 sq ft of waterside balcony space. Sale is subject to terms & conditions of an offering plan.

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.

**Exquisite Nantucket Style Cedar Shake Home with Breathtaking Waterviews** Perfectly situated on one of the most coveted streets in Greenport Village, this 3-bed, 5-bath home has a commanding presence and is positioned perfectly to enjoy wide views of Stirling & Greenport Harbor. Step inside to discover a thoughtfully designed "upside-down" layout that places the main living areas on the upper level, maximizing views of the surrounding waters and enhancing the feeling of openness and natural light. Meticulously crafted with attention to detail, this residence boasts white oak wood floors that exude timeless charm and vaulted ceilings anchored by wood beams for a touch of rustic elegance. The lower level features 2 en-suite bedrooms, a cozy den and laundry. Upstairs has an open floorplan featuring a gourmet eat-in-kitchen with high-end stainless steel appliances & a walk-in pantry, a dining room with water views in every direction, and a living room with a gas fireplace. Through sliding glass doors, step out to the mahogany waterside upper deck to soak in the maritime ambiance or enjoy al fresco dining with a view. Outside, the fully fenced grounds with mature & manicured landscaping create privacy for a peaceful outdoor retreat, all while the vibrant village life awaits just moments away. Ask about the dock slip available for rent. Come see for yourself! It'll be worth your time!

Charming water view first-floor co-op on coveted Sterling Street. The perfect two-bedroom escape in a prime village location. Renovated kitchen, bright living room, waterside sitting porch, large full bath, in-unit laundry, and stunning views of beautiful Sterling Harbor. Have your morning coffee or evening cocktail in the shared waterfront lounge area. Short distance to the villages, many restaurants, shops, and beaches. The unit comes with a detached storage 5x14 storage unit and on-site parking.

Lovingly updated to enhance its 19th-century glory, this enchanting residence invites you to experience a blend of historic charm and modern comfort. Beyond its picturesque facade lies a beautifully renovated home boasting not only timeless elegance but also provides a separate studio space, offering endless possibilities for creativity or relaxation. Step into the lush oasis of the yard, where mature trees and vibrant plantings, including majestic rhododendrons, delicate dogwoods, blossoming crabapples, striking coral bark maples, and the subtle beauty of kerria, create a serene backdrop for outdoor gatherings or moments of quiet contemplation as well as providing room for a pool. Conveniently situated, this idyllic property offers easy access to all that Greenport Village has to offer, ensuring that every amenity, from quaint shops to renowned restaurants, is within reach. Embrace the epitome of refined living in this captivating home, where every detail speaks to a harmonious blend of past and present

Swan Landing, a custom build by award-winning architecture firm, Shope Reno Wharton Associates, was created to exemplify luxury living at the highest caliber. Featured in Architectural Digest and House & Garden, at 23,000 +/- sq. ft. and situated on 5.3 pristine acres of land; this unparalleled estate embodies the essence of strategic architecture and design. The home features a deepwater dock, indoor pool, outdoor pool, beach, tennis court, English garden, guest house, greenhouse and much more.

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.