luxury houses for sale Shelter Island, United States (page 2)

Orient Village- located on a quiet street in the coveted coastal village of Orient, this beautifully maintained 4-bedroom, 2.5-bath home borders preserved land, offering exceptional privacy and a serene natural setting. A welcoming wide front porch sets the tone before entering the foyer, which opens to a spacious living room with a wood-burning fireplace. The home features a large eat-in kitchen, formal dining room, and a sun-filled sunroom overlooking the backyard and gardens. In addition, the first floor includes a generously sized primary bedroom, an additional guest bedroom, and a full bath, providing convenient main-level living. Upstairs, a large loft area offers flexible space for a home office or family room, along with two additional guest bedrooms, a guest bath, and a bonus room ready for your creative expansion ideas. Additional highlights include gleaming wood floors throughout, a large unfinished basement with abundant storage space, and a two-car garage. Ideally located just moments from the Orient Yacht Club, all village amenities, beaches, and the Jitney, this special property presents a rare opportunity to enjoy relaxed North Fork living in one of the area’s most sought-after communities. This is the very special home you have been waiting for.

The crown jewel of Orient Village, the Shaw House/ Revolutionary Cottage was built in 1730 and features 3 bedrooms, 2.5 baths, and an updated eat-in kitchen. Original exposed beams, wide-plank floors, period hardware, 3 updated wood burning fireplaces, custom cabinetry & woodwork. Two large decks span the back of the house overlooking Orient Harbor & Yacht Club. Located in the heart of Orient Village walking/biking to all village amenities. Coming Soon, May 12th.

Beautifully updated & fully renovated in 2020, Arts & Crafts style home in the heart of Orient Village, one block from Orient Harbor, walking distance to post office, country store & all village amenities. Open concept dining/living room with large wood burning fireplace. Updated gourmet kitchen with Thermador 6 burner/griddle stove, Subzero refrigerator, Bosch dishwasher, & wine cooler. Enclosed front porch sunroom. Second floor master bedroom with large balcony overlooking the garden with ensuite bath – 2 sinks, free-standing tub & walk-in shower. Two additional bedrooms and full bath with tub and front-loading washer/dryer. Fenced yard, outdoor shower, backyard deck & lower patio for outdoor dining & entertaining. Professionally landscaped with mature trees and flower beds. Detached 1-car garage.

Welcome to 285 Sandy Beach Road, this newly constructed modern style home is ideally located just outside historic Greenport Village and just steps from a beautiful sandy beach at Norman E. Klipp Marine Park. Upon entry, the foyers 20'+ soaring ceilings create an immediate sense of light and volume, seamlessly flowing into the open great room anchored by a gas-burning fireplace. The home offers a crisp, airy aesthetic throughout and is thoughtfully designed for both everyday living and entertaining. The main level features a first-floor en-suite bedroom, a chef-style kitchen with a large center island, and a generous living anchored by an inviting gas fireplace and dining area ideal for gatherings. The second floor includes two well-appointed guest bedrooms connected by a Jack-and-Jill bath, along with a private primary suite featuring a raised deck with peek-a-boo water views and a spa-inspired en-suite bath with soaking tub, walk-in shower, and double vanity. Additionally, the property offers ample room for a pool, presenting the opportunity to further elevate this home into a true resort-style North Fork retreat.

Recently transformed with a stylish new renovation, this turn-key contemporary retreat is set on 1.6± exceptionally private acres backing directly onto a breathtaking 56-acre town reserve. Surrounded by protected natural beauty and located near one of the area's most pristine bay beach communities, the property offers an increasingly rare combination of modern luxury, tranquility, and seamless access to the Hamptons lifestyle. Hidden behind lush landscaping and enveloped by reserve land, the setting feels remarkably secluded and serene. Just moments from Sammy's Beach and Cedar Point, the home is ideally positioned to enjoy kayaking, paddle boarding, sunset walks, and easy access to both Sag Harbor and East Hampton Village. Inside, more than 4,000± square feet of beautifully reimagined interiors are designed for effortless indoor-outdoor living. Natural light pours through oversized windows and skylights, illuminating soaring ceilings, refined finishes, and an airy open layout. At the center of the home is a stunning chef's kitchen anchored by a dramatic 9-foot waterfall island, premium stainless steel appliances, and seamless flow into the dining and living areas. Multiple sliders open to expansive mahogany decking, creating an effortless connection to the outdoors, while a towering fieldstone wood-burning fireplace adds warmth and character to the main living space. The thoughtful floor plan on one story with finished lower level includes the primary suite occupying its own private wing behind a sliding barn door and featuring a spa-like bath with heated floors, freestanding soaking tub, oversized shower, and a spacious dressing room. The finished lower level enhances the home's turn-key appeal with a large guest suite, spa bath, sauna, dedicated laundry room, pantry with additional refrigerator, and separate entrance-perfect for extended stays or flexible entertaining. Outside, the property unfolds like a private resort in total privacy. A 20x40 pool is surrounded by mahogany decking, complete with hot tub, multiple lounge areas, and outdoor dining spaces. Elegant, modern, and completely move-in ready, 56 North Woods Lane is a rare offering in one of East Hampton's most desirable bay beach enclaves-where stylish design, total privacy, and protected natural surroundings come together effortlessly.

Newly built modern estate on approximately 3.65 acres overlooking Fresh Pond and Sag Harbor Bay. Located in coveted North Haven, less than one mile from Sag Harbor Village, this 8,960± SF residence offers privacy, scale, and proximity to beaches, marinas, and dining. The home features 8 bedrooms and 8.5 bathrooms, with expansive glass walls, a double-height foyer, and open-concept living areas designed to maximize natural light and water views. The chef's kitchen includes Sub-Zero and Wolf appliances, marble countertops, an oversized island, and a full butler's pantry. Indoor-outdoor living is emphasized with multiple covered porches, terraces, and retractable glass doors. The main level includes a junior primary suite with spa-like bath and sitting room, along with additional living, dining, and service spaces. The upper level offers a water-view primary suite with dual walk-in closets and a luxury bath, plus five ensuite guest bedrooms and a secondary lounge with wet bar and terrace access. Outdoor amenities include a 20' x 50' heated gunite infinity-edge saltwater pool with spa, limestone patios, mahogany terraces, and a 320± SF pool house with kitchenette and firepit. The property also allows space for a future pickleball or padel court. A refined North Haven offering combining modern design, privacy, and convenient access to Sag Harbor Village.

Newly built cedar-shake estate on approximately 2.37 acres overlooking Fresh Pond and Sag Harbor Bay. in coveted North Haven. Offering 8,030± SF of living space, this traditional-style residence blends classic Hamptons architecture with modern scale, just minutes from Sag Harbor Village, marinas, beaches, and dining. The home features 7 bedrooms, 7 full and 2 half bathrooms, with wide-plank white oak floors, tray ceilings, and a wood-burning fireplace anchoring the main living spaces. Walls of sliding glass doors create seamless indoor-outdoor flow and enhance natural light throughout. An eat-in chef's kitchen with premium appliances serves as the heart of the home, complemented by a first-floor office/den. Multiple living and dining areas provide flexibility for everyday living and entertaining. Upstairs includes a beverage center, spacious bedroom suites, and two rear balconies with pond and bay outlooks. The layout is designed for comfort, scale, and easy living. Outdoor amenities include a 20' x 50' heated pool with bluestone patio, covered dining and lounge areas, and a fireplace-centered outdoor living room for year-round enjoyment. A rare highlight is the opportunity to add a 2,500± SF guest house, offering exceptional flexibility for future expansion. A refined North Haven offering with water views, privacy, and timeless design close to Sag Harbor Village.

Built in 1868, this historic Greenport Village home is brimming with character and ready for its next chapter. Set on a .25-acre lot, the home features large spacious rooms, 3 bedrooms, 1.5 baths, beautiful built-ins, and a wood-burning stove. The home presents an exciting opportunity for thoughtful restoration and personalization, allowing the next owner to enhance and reimagine the space while honoring its original details. A rear deck extends the living space outdoors, while a substantial barn at the back of the property opens the door to endless potential as a studio, workshop, or inspired retreat. The expansive yard provides room to entertain, garden, or simply enjoy the privacy and openness seldom found within the village. Ideally located just a short distance to Greenport’s vibrant shops, restaurants, park, waterfront, bay beach, LIRR & Hampton Jitney. A unique opportunity to own a piece of Greenport history with space, flexibility, and an unbeatable village lifestyle.

This expansive North Fork property offers idyllic privacy, boundless potential, and exceptional versatility across three separate parcels. The spacious 4-bedroom, 4.5-bath main residence awaits your finishing touch - customize and craft your dream home exactly as you envision. Ample natural light, flexible open spaces, and generous proportions provide a canvas ready for refinement inside and out. A single and separate buildable 3/4 acre parcel offers a charming, 2-bedroom, 1-bath cottage offers ideal accommodations for guests, caretaker quarters, rental opportunity, investment, or expansion. This unique estate is agricultural-zoning with development rights sold land. Currently operating as a thriving privet farm, featuring 16,500 mature California Privet shrubs and an additional 8,000 seedlings - yielding opportunities for wholesale, landscaping, and horticultural expansion. Embrace the outdoors with tranquil features including a picturesque pond, a greenhouse for year-round cultivation, and extensive grounds perfect for farming, equestrian pursuits, or simply a peaceful sanctuary away from the hustle and bustle. The layout and multiple outbuildings offer versatility for hobby farming, horses, or creative pursuits. Whether you seek a working agricultural venture, a retreat, or an extraordinary setting for your next chapter, this exceedingly rare North Fork treasure presents an unparalleled opportunity in a coveted location. Could Be You!

You have to come see this house with me—because it’s got that real “grandma’s classic 1940s winter weekend” energy in the best way.Picture this: it’s snowing outside, and we’re posted up in the big living room with the granite fireplace going. Knotty pine paneling, bookshelves built in on both sides of the hearth, and that warm glow that makes you feel settled. We’ve got Monopoly spread out on the coffee table, a huge bowl of popcorn (the legit kind made on the stove), and a record playing… then playing again… then somehow playing again because that’s what happens in houses like this.And of course there’s always that one person who breaks out a slide projector, vacation slides from back in the day with the vintage clothing, the hair styles, taking in the moments. This house just fits that vibe perfectly.Then you walk into the sunroom and it changes gears: slate floors under your feet, water views straight out toward the beach, and it becomes the reading and lounging zone. Newspapers, magazines, tuna melts, tomato and rice soup. It’s basically the best relaxing room.Outside, it’s the kind of winter that makes you want to actually do stuff: sledding down Munn Lane, then heading to the Causeway beach to see what the sea rolled in, perfect for seaglass collecting. That whole shoreline exploration where you come back with cold cheeks and a pocket full of little treasures.The layout is great too, wood floors through most of the house, and there’s that first-floor bedroom space (or den) with water views across the street that ties the whole country home feeling. It’s cozy, practical, and somehow still feels special.And the garage… three bays, but it doesn’t feel like “just a garage.” It feels like a workshop where projects are always in motion. The kind of place where sleds, bikes, paddleboards, clam rakes, fishing poles, beach chairs, and coolers all have a home.Here’s the kicker: it comes with two pieces of land, including the waterfront property across the street. So those water views? Protected. There’s about 50 feet of sandy beach, and the path to the water is right across the street, perfect for kayaking or paddleboarding in the summer. And sitting on the hill, the elevation is high enough that you’re not sitting stressing about flood issues.In the summer you’re up on the hill watching fireworks in Orient Village, with views from the living room, sunroom, and that main-floor bedroom/den. It’s peaceful, authentic, and it feels connected to the real local story—ice boat racing off Narrow River Road, oyster farming, clamming, fishing… all of it.This is what relaxation looks like when “country” means coastal, classic, and actually real. You don’t just tour this house—you feel it. Orient Country Living.

A rare opportunity to own a beach house on an elevated site with beautiful water views. Perched on a hill, this three-bedroom retreat is filled with natural light streaming through expansive windows that frame the water beyond. Update and reimagine the existing home to suit your vision or create your dream house on this exceptional property with room for expansion and a pool. Launch a kayak or paddleboard from a nearby path just across the street, or enjoy the sandy bay beach only moments away, surrounded by native flora and fauna. Located in the highly sought-after Sammy's Beach area, known for its tranquility and natural beauty.

Experience the pinnacle of refined living in this completely reimagined home, boasting a comprehensive renovation and redesign led by a professional interior designer. Every square inch has been thoughtfully curated, starting with the custom front door featuring openable screened sidelights that welcome you inside. Premium oak hardwood flooring flows seamlessly throughout the main living areas, grounding the home in natural warmth and elegance. The heart of the home, the great room and large kitchen, is an entertainer's dream, featuring gas fireplace, a dry bar with a wine fridge, premium lighting and plumbing fixtures, quartz countertops and custom window treatments including blinds and valances. First floor also includes a light filled den and separate office space for working at home. Retreat to the spectacular owner’s suite, a true sanctuary defined by architectural ceilings with shiplap details and a custom walk-in closet. The en-suite bathroom is clad in Italian marble and featuring premium fixtures. Indulge in the luxury of radiant floor heating—which extends into the large, curbless spa shower with its sleek infinity drain. Your guests are treated to equal luxury; guest baths feature premium fixtures and their own radiant floor heating. The guest bedrooms offer cozy carpeting and custom woodworking with the twin room featuring blackout and light-filtering shades for perfect rest. Behind the walls, the home is just as impressive. A whole-house water softening and purification system, smart irrigation system, and 2-zone heat/AC with smart thermostats ensure comfort and peace of mind. This is more than a renovation; it is a complete lifestyle upgrade. Located close to the heart of downtown Greenport Village and its bayfront beaches and transportation hub.

Orient – Set high above the Long Island Sound in the storied enclave known as The Hill, this rare offering captures the essence of classic Orient living. Authentic, timeless, and grand in scale, the home showcases architectural details including five fireplaces, elegant 16-over-1 windows, and a front entry framed by original sidelights. The 1.3-acre grounds unfold across rolling terrain with mature landscaping, stonework, and meandering garden paths. A sparkling swimming pool sits tucked into the landscape, creating a private retreat. Inside, generous rooms and a waterside screened porch invite gatherings large and small, all set against the backdrop of unforgettable sunsets. The home offers space, character, and endless potential. Cherished by the same family for 65 years, it now awaits its next steward. Properties of this caliber and in this location are exceedingly rare. It doesn’t get more quintessentially North Fork than this. A truly special Orient opportunity.

Okay, so the first thing, you get out of the car and this farmhouse style has the front porch that actually has room for a side table and chair to have my morning coffee in peace that I have wanted so badly. Then inside, the half bath is right next to the front door, but it's tucked far enough away from the open living room and kitchen that it doesn't feel awkward when all of us are hanging out. The kitchen has the paneled fridge, a real pantry closet and open shelves that I have always liked. The kitchen sink is setup where I am staring out to the backyard when I am stuck doing dishes, so good. They even say there is room for a pool. Then the dining room has this full glass slider to the yard, so the whole back of the house is just filled with light, you can even see the view of the yard from the living room. Upstairs, the ensuite bathroom is honestly my favorite surprise, the floor is so interesting, and the whole space feels calm with the finishes they picked. Even the downstairs bathroom has this beautiful wallpaper that makes this new construction feel intentional, not an afterthought. What I love is this location makes you feel like you found a secret corner of Greenport. You're literally tucked up against the maple tree forest, so it's quiet and green in the best way. The backyard is fully fenced so if the decision is for the pool, it doesn't feel tight. And because this one is New Construction, everything just feels solid and reliable. Best part, the house is also a half mile away from the LIRR train station and Hampton Jitney stop to get to NYC, then Aldo's coffee shop is a 3 minute bike ride or 10 minute walk. I think this might be the one, you have to come see it.

Opportunity knocks! This rare farmhouse style cottage rests on an expansive double lot on the edge of Greenport Village and is prime to be revamped. Featuring 1700sqft of interior space, a large block foundation with full basement throughout most of the footprint, a 12x22 detached garage and a yard that will allow your imagination to run wild. Walk into town, walk to 5th and 6th street beaches and easy access to all that the North Fork has to offer.

Welcome to 619 Bailey Avenue, a fully restored and move-in ready farmhouse located on the fringe of Greenport Village. Originally part of a larger North Fork farm and estate, this incredibly well appointed circa 1900 residence has been thoughtfully re-imagined to blend modern conveniences with preserved period details. Original features such as hardwood floors, detailed millwork/moldings, and classic architectural elements have been carefully maintained, while updates throughout provide comfort and functionality. The custom kitchen is a standout, featuring a 48 range, oversized center island, custom cabinetry, and an 8-foot bi-fold glass door that opens to the rear yard, creating seamless indoor-outdoor living. The first floor offers a well-balanced layout with a spacious living room with wood-burning fireplace, formal dining room, dedicated home office, powder room, and a flexible bedroom or bonus space. Upstairs, the second level includes two guest bedrooms and a full hallway bath, along with a primary suite featuring vaulted ceilings, a large walk-in closet, and an en-suite bathroom with double vanity and a walk-in shower with a dual shower head system. The rear yard is expansive and private, complemented by a detached one-car garage. Not to mention, there is also an active permit in place for a 16' x 32' in-ground pool, a perfect opportunity to take this rare offering one step further. Conveniently located near Greenport Village's business district, Kontokosta Vineyard, Bay/Sound Beaches and Sep's Farm-stand, this amazing offering is sure not to last!

This charming Greenport cottage blends warmth, character, and easy coastal living just moments from Greenport Village. Located only a short stroll from Main Street, shops, restaurants, and the waterfront, it offers the rare combination of village-adjacent convenience while still feeling peaceful and residential. Full of natural charm, the home features a comfortable two-bedroom layout with a relaxed, inviting feel throughout. It’s the kind of space that immediately feels easy to settle into, with potential to enhance over time. Out back, a deck and separate patio create seamless indoor-outdoor living—perfect for morning coffee, summer dinners, or quiet evenings at home. The outdoor space becomes a true extension of the home and adds meaningful lifestyle value. Filled with character and opportunity, this is a special chance to enjoy the best of Greenport living—walkable to everything that makes the village so desirable, yet tucked into a quieter setting with a true North Fork charm.

Level .919-acre lot in Hillcrest Estates, Orient, NY. Beautiful site with electric and natural gas in the street. Close to Orient State Park, Orient Village, Truman’s Beach, Sound and Bay Beaches. A short drive to Greenport Village for shopping and restaurants.

Welcome to 150 Hillcrest Dr N, located in Hillcrest Estates. This offering is a to be built opportunity and the images are of another Orient property that this builder wrapped up in 2023. At this point, a very similar style home can be built on this lot or the builder can be hired to do a custom build and tailor the property to a buyer's specifications. The property is elevated, slopes gently SW and will offer sweeping farm/water-views over Orient and out to Narrow River and Long Beach Bay. More information on previous Orient projects can be provided by request or bring your plans and allow your vision for your forever home to come to life!

Well maintained private home in the beloved Green Acres beach community with sound beach at end of road. .63-acre lot that backs onto 63-acres of pastoral undeveloped preserved land. The home features oak floors throughout, 2 bedrooms, 1 full bath, 1-car garage, and shed. Full second floor bonus space and storage under roof eaves. Close to Orient Village and renowned Orient Beach State Park.

The pinnacle of Luxury Living In the historic heart of Sag Harbor — a village shaped by its storied whaling past and now celebrated for its cultural sophistication — Residence A stands as a singular architectural statement along one of the most coveted stretches of waterfront. Commanding approximately 250 feet of prime frontage on the harbor, this exceptional estate is far more than a home; it is a four-level masterwork of glass, stone, and light, created for a global buyer seeking complete privacy, effortless luxury, and direct nautical access.This extraordinary property is the result of a visionary collaboration between J. Bialsky of Bialsky Premiere Design & Development and the internationally acclaimed Hollander Design Landscape Architects. Together, they have crafted a residence that exists in perfect harmony with the Peconic Bay — a seamless dialogue between architecture, landscape, and water. Every line is intentional, every perspective framed, and every material selected to endure the coastal environment while maintaining an elevated, timeless aesthetic.Spanning an impressive 16,974 square feet across four levels, the estate is conceived as a vertical sanctuary where grand-scale entertaining and intimate retreat coexist effortlessly. Interiors encompass approximately 12,551 square feet of meticulously designed living space, defined by a palette of organic textures, refined finishes, and state-of-the-art systems. The residence offers eight expansive bedroom suites and ten beautifully appointed baths, thoughtfully arranged to accommodate family, guests, and live-in staff with complete comfort and privacy.Outdoor living unfolds across multiple levels of tiered terraces and lounge decks, creating a dynamic al fresco experience that keeps the water constantly within view. At the pinnacle, a private rooftop sanctuary serves as a crowning architectural achievement — featuring a pool and spa seemingly suspended above the harbor, offering uninterrupted 360-degree vistas and breathtaking sunset views across Sag Harbor’s golden coastline.For the yachting enthusiast, the property delivers a level of functionality rarely found in village waterfront estates. A private, deep-water marina includes two 60-foot boat slips, placing you at the center of the Hamptons’ maritime lifestyle with immediate access to the open Atlantic and the protected waters of Shelter Island Sound.Beyond its beauty, the residence operates with the precision of a modern high-security retreat. A rare private garage provides secure parking in the heart of the village, while fully integrated smart-home technology manages climate, lighting, and security seamlessly from anywhere in the world.Turn-key in every sense, Residence A represents a rare convergence of location, design prestige and waterfront capability — an exceptional offering for the most discerning buyer seeking a legacy property in one of the Hamptons’ most iconic destinations.

Freshly updated and effortlessly stylish, this Sag Harbor retreat includes coveted private beach access. Sunlight pours through the home, creating a bright, airy atmosphere that feels as inviting in the off-season as it does at the height of summer. The interior offers five well-proportioned bedrooms and 3.5 beautifully finished marble baths, along with a seamless open-concept layout. A modern kitchen flows into the dining and living spaces, ideal for both relaxed everyday living and entertaining. Outdoors, a heated gunite pool with spa anchors the backyard, offering a perfect setting for warm-weather enjoyment. Upstairs, the primary suite features a generous private balcony overlooking the grounds, providing a quiet escape. Just minutes from both Sag Harbor Village and East Hampton, this property strikes the perfect balance between convenience and tranquility.

Perched at the highest elevation on coveted Cliff Drive in Bay Point, Sag Harbor, this rare opportunity offers sweeping western sunset views over Peconic and Noyack Bays. Renovate, reimagine, or build your own custom waterfront retreat in one of the Hamptons' most desirable waterfront communities. Bay Point captures the charm of classic coastal living with boating, kayaking, and nearby Long Beach, all just minutes from the restaurants, marinas, galleries, and boutiques of Sag Harbor Village. The existing home is offered as-is and awaits a visionary buyer ready to unlock the extraordinary potential of this exceptional setting. Whether restoring the current residence or creating a brand-new coastal masterpiece, this is a rare chance to own a premier sunset-view property in Sag Harbor.

Custom renovated 1920's Long Island Potato Barn with pool, set on .83 acres in Orient. Large foyer with 2 closets. Expansive open concept living/dining/kitchen with wood burning fireplace and sliding doors leading to the brick patio and garden. Master ensuite bedroom with full bath with tub & stall shower, 2 additional bedrooms, full bath, and laundry room. Spacious full basement with high ceilings that was formerly used as a workshop. Exceptional privacy with mature landscaping, heated in-ground pool, brick patio for entertaining, 2 accessory outbuildings. Association Sound Beach rights. Proximity to Orient State Park, Orient Village amenities and marinas. 24 hr. notice for showings.

This charming cape is situated in Greenport, just minutes from Greenport Village and Beaches. The home has 4 bedrooms, 2 full bathrooms, and approximately 1500 sq ft. The eat-in kitchen has granite countertops and an awesome backsplash. The basement is unfinished with bilco doors. There is a fenced backyard and 1 car garage. The home currently has tenants, who will be leaving.