Shelter Island Heights NY Real Estate & Homes for Sale

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.

Stylishly Renovated in Shelter Island Surrounded by the natural beauty of Shelter Island, this stylishly renovated Mid-Century 'A-Frame.' Located on a quiet road and blending minimalistic, well-designed interiors with the comfort of refined designer furnishings, this 2 bed/2 bath home, with a bonus loft 'meditation room', purposefully maximizes the experience of inside/outside living. Floor-to-ceiling sliding doors allow a seamless flow between the house and the surrounding decks, patios & gardens, whilst the dappled light from surrounding trees and native plantings creates a wonderful ambiance to a series of outdoor rooms. A large, decked entertainment area looks over the architectural proportions of the 10' x 40' saltwater pool, complimented poolside by a row of sun loungers and umbrellas which lead to a chic pool house, with an additional bathroom and low lounging sofa. 2 outdoor showers, a shaded ping pong table, fire pit 'hang out' and outside grilling area complete the exterior picture. An adjoining garage and laundry room are found on the lower level, accessed by a spiral staircase. Eat-in, Henrybuilt Kitchen, with appliances from Fisher & Pakel. Restoration Hardware. Enjoy scenic ferry access to explore both the North Fork. Mashomack Nature preserve, Hay Beach and Coecles Marina are within short driving distance.

Newly 2024 Renovated 4 Bedroom 3 Full Bath Ranch in Desirable Location of Greenport Harbor & Sandy Beach. Enter to Soaring Ceilings and Beautiful Wood Flooring. Featuring open concept Great Room complete with a stunning Quartz Top Center Island, Bar and Wine Refrigerator perfect for easy entertaining. Kitchen Features: Soft Close Cabinetry, Quartz Cabinets and New Appliances. Master Bedroom w/ New Master Bath, 3 Additional Bedrooms, 2 Additional New Bathrooms, Laundry Room. Garage -3 Car Deep. New Siding, Windows, Roofing, Gutters, Energy Efficient Electric Heat & CAC, Electric and All Exterior and Interior Doors. New Driveway, Front Walkway and Stoop. The area offers proximity to parks, vineyards, farms, beaches, restaurants, and night life. Whether you are looking for a seasonal retreat or a year-round residence, this property presents a great opportunity to live near the beach in a relaxing lo key environment.

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.

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.

Summer Has Almost Arrived- Make Your Dreams Come True In This Cottage By The Sea. Cute 3 Bedroom, 1 Bath Ranch Located On Sutton Place, Where Sunsets On The Beach Are Only A Few Steps Away. Don't Miss This One Awaiting Your Magic Touch!

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 your Bay Front paradise on the North Fork! This home has every aspect of beach living. Incredible views of Bug Light and Shelter Island. Two lots comprising 1.38 acres and over 286 feet of expansive sugar sand beach. Featuring an open gracious floor plan. 5 bedrooms, 4 baths, wraparound porch, outdoor shower, waterside gunite pool, outdoor kitchen area, a garage that houses a gym, living loft area and a full house generator! The additional lot has a building envelope for a 2700+ square foot home. The beauty of all of this and located in Flood Zone X! Surrounded by North Fork renowned farm stands, restaurants, beaches, marinas, boating, award winning wineries and great shopping.

Down a graceful country road, on the North Fork of Long Island your dream home awaits. Sprawling over 13 acres with 354 feet of waterfront on Arshamomaque Pond leading out to the Peconic Bay. There is a 20 x 40 gunite pool, a barn with horse stalls should you choose or for use as an art barn! Plenty of room for tennis. Inside this magical home is an exceptional chef's kitchen with a Wolf range, butler's pantry and plenty of entertaining space - including a generous fireplace and a 3 season porch. There are two wings - one which has 3 ensuite bedrooms, including the primary suite. The other has a full kitchen, two bedrooms and 1 bathroom. This home also features a wine cellar and walkout basement. A property of this caliber does not come to the market often on the North Fork of Long Island. Let's make your dreams come true - this could be you!!

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.