Shelter Island Heights NY Real Estate & Homes for Sale

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.

Introducing 165 Angler Rd, a beautifully custom-designed,new construction home that fulfills every buyer's wish list. Positioned just steps from a pristine Bay beach and in close proximity to Greenport Village's vibrant waterfront district, this residence boasts a sophisticated spa-like heated in-ground pool with a stone patio surround and is incredibly well appointed, seamlessly blending traditional details with chic modern elements. With three floors of finished space including a fully finished basement hosting a home office, media room, and full bathroom, this home offers versatile living options. The main level features 9ft ceilings with a light-filled open Great Room, a first-floor bedroom and bathroom, while the third level features two guest bedrooms sharing a full bathroom and a generously sized primary bedroom with a private full bathroom and an oversized walk-in closet. The superb craftsmanship of this home is evident in the custom millwork, built-in shelving, rift and quartered hardwood floors, and upscale finishes. Equipped with dual-fiber-optic cable lines and Cat6 ethernet in all bedrooms and living spaces, this home provides an ideal work from home environment and remote monitoring capabilities for added convenience. The chef's kitchen is designed for culinary enthusiasts, featuring GE Cafe appliances, wall-to-wall stone counters, wine fridge, floating shelves, built-in wine storage, and a large center island, perfect for year-round entertaining. This exceptional Greenport residence offers the perfect blend of sophisticated finishes, modern amenities, and a prime location. Not to mention, you will enjoy world class vineyards, local breweries, hiking trails and many additional beach options between the Great Peconic Bay and LI Sound.

This is your opportunity to watch your home be built from beginning to end. This 4 bedroom 3.5 bath has an en-suite bedroom/bath on the first floor and the second. Hardi-plank siding, Anderson windows, architectural roof shingles, hardwood floors throughout, quartz and or granite counters, and custom tile. Greenport is a quaint pedestrian friendly village filled with activities and opportunities like a deep-water marina, fishing excursions, Shelter Island Ferry, restaurants, shopping, movie theatre, Mitchell Park, carousel, galleries, golf course, and sound & bay beaches. Build your dream home in this beautiful beach community. Taxes represent land only.

Renovated Greenport Village Farmhouse with custom woodwork details throughout! With a simplified way of living, the location is amazing and the spaces have been uniquely well designed to maximize the use of space and quality craftsmanship. The yard and hardscapes were installed with the designs of coastal village landscape architect offering low maintenance patio, grilling station and paper birch creating year round visual interest. The front porch is wrapped in red cedar and is so cute its the envy of the neighborhood. The interior offers custom kitchen cabinetry, main floor laundry and a full bath on both levels. On demand hot water recently installed for energy efficiency to keep you warm in the winter and energy efficient central air to keep the summer season cool and fresh! The marinas, waterfront dining, beaches, golf course, vineyard tasting rooms encompass this Farmhouse so there is no reason to be bored. The bus, train, ferry and Greenport Village shops and destinations create so many opportunities to explore al that the village living has to offer.

Adorable with room to grow! This complete renovation kept the character and opportunity to expand on this corner property to create your dream yard. Just blocks away from marina's, sandy beaches, tasting rooms and more. Extensive renovation in 2021 with windows, doors, roofing, siding, insulation, electric, plumbing as well as new baths and kitchen creates the perfectly crafted space with wood ceilings, original wood floors and more.

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. Ascend beyond the initial allure of two bedrooms on the first floor to discover the expansive potential of the second floor-a canvas awaiting your personal touch. With soaring 14-foot ceilings and Board of Health approval for four bedrooms, the addition of two more bedrooms opens endless possibilities to customize this space according 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.

Deep Water Oasis Tucked Away In A Protected Cove- Don't Miss This 4 Bedroom, 3 Bath, Modern Sun-Drenched Colonial With Plenty Of Deep Water Dockage For Several Boats, 270 Degree Water Views Directly Across Peconic Bay To Shelter Island. Privately Situated On 1.4 Acres At The End Of A Cul-De-Sac. Home Features Two Fireplaces, Wine Cellar, Gourmet Kitchen And Many Updates Throughout. Whole House Generator, Dock Has Water & Electric.

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!

LOOKING FOR PARADISE? Let me take you through this stunning waterfront condo in one of the most desirable spots on the North Fork, Greenport, with breathtaking views of the Peconic Bay and Shelter Island. This condo has an updated eat in kitchen, updated bathroom, a nice size living room, high ceilings, and windows that rain in tons of natural light throughout. On this 4 acre natural beachfront property, you can enjoy the convenience of having a newly redone tennis court, basketball court, and swing set, just a stone throw away. The property includes a large private storage unit for each condo which is great for storing all your outdoor gear and much more. It also has a common area which is inclusive of the deck, bathroom, rinse shower, a community kitchen, and sunbathing chairs to make your time at the private beach more relaxing and comfortable. The private dock gives you easy access to hop on your boat and explore the surrounding waters. Boat slips have a nominal fee of ONLY $700 FOR THE ENTIRE SEASON. Who says you just have to be on the water? You are not in the mood for water sports today? Then lets go golfing. Just minutes away is the beautiful Islands End Golf Course welcoming all. The always lively town of Greenport with its variety of bars, restaurants, and shops, brings a world of entertainment and is perfect for an evening or night out. This waterfront condo offers a perfect blend of serenity, accessibility, entertainment, and is a dream for anyone looking for the vacation lifestyle. Don't just imagine it, come out and see for yourself!

Design your paradise! Just over one acre of land to dream and create your ideal home. 60800 County Road 48, Greenport is conveniently located and abuts 53 acres of a nature preserve to deliver the ultimate privacy and serenity. Currently has two existing structures on the property, a residential home as well as a two car detached garage. Sold "As Is"

Indulge in the ultimate waterfront lifestyle at this beautiful condo complex, where this ground floor garden apartment boasts breathtaking direct bay views. Meticulously maintained, this unit features a spacious renovated kitchen, an expansive bedroom, and a generous waterside deck. Whether you're enjoying the sunrise from your living room, views from the beach, marina, poolside, or your own deck, this residence provides a tranquil escape. The property's 16-acre grounds boast top-notch amenities, including a gunite pool, two tennis courts, three pickleball courts, a basketball court, clubhouse, gym, sandy beach, private marina, and beachside kayak and SUP storage. Just under a mile from Island's End Golf Course and a short two-mile drive to Greenport's shopping, dining, movies, wineries, and more, this is your effortless gateway to waterfront living

Location, Location, Location! Experience the luxury of waterfront living in this prime first floor, one bedroom, one bath North Fork condo. This coastal panoramic beauty could be all yours plus a private sandy beach, private marina, community clubhouse, gym, 3 pickle ball courts, 2 tennis courts, 1 basketball court and in-ground pool all on 16 seaside acres. Conveniently located to golfing and to renowned Greenport...enjoy all the NoFo has to offer - vineyards, boating, fine dining, shopping and more!

Another beautiful new construction home by one of Long Island's most coveted construction companies, Modern Age Home Builders! 2350 Shipyard Ln features a European style modern design home just under 4,000 sq ft. just steps from the beach and a detached oversized 2 car garage, all sitting on over 1.5 acres of land. The first floor consists of a large foyer that leads to an open and airy great room and kitchen which is perfect for entertaining guests and hosting gatherings. The great room has a gas fireplace, surrounded by a stunning quartz. The kitchen is finished with custom 2 stage cabinets, custom quartz countertops, and a top of the line 7-piece appliance package. There is also a living room, dining area, mudroom, half bath, and master ensuite. The second floor consists of a master ensuite, 3 secondary bedrooms, and 2 additional full bathrooms. Additionally, there is a study, laundry room (including a washer and dryer), as well as a loft which can easily be converted into an addition bedroom or anything else you desire! All closets are dressed with custom wood shelving and all bathrooms consist of custom cabinets, quartz countertops, and imported Italian tile. The master ensuite and loft each have their own balconies. The home also has a large, nearly 2,000 sq ft, semi-finished lower level which is ready to use as is or you can truly make it your own. It has large egress windows that allow for natural light, perfect for finishing. There are two covered patios in the back along with a 20' x 40' inground swimming pool and a private path leading directly to the beach!

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.

This spacious cape in coveted Eastern Shores boasts soaring cathedral ceilings, allowing abundant natural light to fill the home. Its versatile floor plan features a newly renovated kitchen, multiple great rooms, and four full baths, making it an ideal space for hosting friends and family. Read a book by the large fireplace or relax on the rear deck and patio; the yard offers room for a pool. Located just two blocks from your picturesque association beach and less than a mile from Greenport Village shops and restaurants, this property exudes style and personality while offering both convenience and tranquility.

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.

There is nothing like this beautifully renovated farmhouse on the market. This home is located in one of the most valuable towns on the North Fork. A masterpiece of craftsmanship, this home begins with a beautiful wrap around porch complete with ceiling fans where you can enjoy a private and serene setting. Upon entrance through the foyer, you will be amazed by the exquisite eat in kitchen with high quality finishings and granite countertops. On the first floor there is a dining room, living room and a first floor bedroom en suite with access to the backyard and an additional half bath. Old world charm meets modern conveniences, throughout the home as there are original features such as the wood floors, moldings and the magnificent banister on the stairs. On the second floor there is the master bedroom en-suite, third bedroom and an additional half bath. There is plenty of room for a pool on the beautiful and sprawling property outlined with evergreens for complete privacy. Every detail has been finished to perfection. In the surrounding area you will find Truman's beach, Orient State Park, nature preserves, the lavender farm, wineries, shops and farm stands with Greenport village just a few miles away. Make this home your North Fork dream.

This charming ranch-style home offers a picturesque setting at the end of Ruch Lane, boasting water views of Hashamomuck Pond. Situated on a generous half-acre lot, the property presents an ideal canvas for single-story living or potential renovation and expansion opportunities. Approved Southold Town building permit in place for a stunning five-bedroom, 4.5-bath residence complete with a pool and detached garage. Plans are available for review at showings. Scaled-back expansion utilizing the oversized two-car garage and full basement offers another avenue for customization, providing flexibility to tailor the property to suit specific needs and preferences. Just minutes from Southold Hamlet and Greenport village and a quarter mile deeded sound beach access.

Just steps away from Town beach with water view, this 3 bedroom 3 bath newly renovated home can be yours! This house was just renovated in 2017 and sits on a .39 acre lot right across the street from the long island sound. The first floor features a large living room with tons of windows, brand new kitchen with granite countertops, stainless appliances, new cabinets, and tiled floors. The dining room is surrounded by large windows that overlook the backyard and has sliding glass doors that lead to the deck outside. The first floor has two large bedrooms with one of them having a full bathroom. The second floor of the house is one large bedroom with another full bathroom and walk-in closet. This space can be used as a full floor master suite or can be split up into three bedrooms. The home has an outdoor shower, sprinkler system, alarm system, new custom window shades, washer/dryer, brand new vinyl siding and a forced air-cooling system. There is also a detached one car garage and a private driveway. The house can be delivered fully furnished. Don't miss the opportunity to own a piece of the North Fork!

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.

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.

New construction ready in June. 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.

This great Greenport beach house is the one you've been waiting for! Ten steps down to 100 feet of beach/ waterfront on the Long Island Sound. 4 bedrooms, 2 baths, 1 car attached and detached 2-car garage with a loft, screened in gazebo and a Bocce court on just shy of an acre! Plenty of room for a pool. This won't last! Near all the North Fork has to offer - award winning vineyards, renowned restaurants, farmstands, boating and great shopping!

This 5 bedroom, 4 full bathroom home offers a truly luxurious living experience. The open concept design seamlessly connects the kitchen to the dining and living areas, creating a warm and inviting space for gatherings. Step outside and you'll discover a true oasis. The inground pool invites you to cool off during hot summer days. The beautiful stone hardscape finishes add a touch of elegance and sophistication to the outdoor space, creating a serene atmosphere for outdoor entertaining. Set on a generous .92 acre lot, you'll have plenty of space to enjoy outdoor activities, whether it's gardening, playing sports, or simply taking a leisurely stroll. The well-manicured grounds provide a picturesque backdrop for the home. One of the unique features of this property is the accessory apartment with a separate entrance and a fully equipped kitchen. This additional living space offers flexibility and versatility, allowing for multigenerational living or a private guest suite. Close to beaches, wineries, town and restaurants!