luxury houses for sale Orient, United States

Coastal Living, Without the CrowdsnSet along one of East Marion's most coveted waterfront stretches, 785 The Strand offers a rare blend of privacy, natural beauty, and effortless coastal living. Experience quiet luxury with direct beach access-without the crowds. Perched above the shoreline and directly across from the Long Island Sound, this thoughtfully designed residence captures the understated elegance of the North Fork lifestyle. Surrounded by mature landscaping and sited to take full advantage of its coastal setting, the .56-acre property features a light-filled, two-story home with five bedrooms and four baths, complemented by an oversized pool, two fireplaces, and multiple outdoor spaces designed for both entertaining and relaxation. Open, airy, and filled with natural light, the home is designed to maximize comfort and connection to its surroundings, which include protected Pebble Beach-communally-owned no development lots to the east and south. Expansive windows frame the landscape, while clean architectural lines and warm finishes create a refined yet relaxed atmosphere. Here, beach access is part of everyday life, not an occasion. Also ideally located near marinas, farm stands, wineries, golf courses, and a short drive to Greenport Village. This is a rare opportunity to own in one of the North Fork's most desirable and tightly held locations.

Set along one of East Marion's most coveted waterfront stretches, 785 The Strand offers a rare blend of privacy, natural beauty, and effortless coastal living. Experience quiet luxury with direct beach access-without the crowds. Perched above the shoreline and directly across from the Long Island Sound, this thoughtfully designed residence captures the understated elegance of the North Fork lifestyle. Surrounded by mature landscaping and sited to take full advantage of its coastal setting, the .56-acre property features a light-filled, two-story home with five bedrooms and four baths, complemented by an oversized pool, two fireplaces, and multiple outdoor spaces designed for both entertaining and relaxation. Open, airy, and filled with natural light, the home is designed to maximize comfort and connection to its surroundings, which include protected Pebble Beach-communally-owned no development lots to the east and south. Expansive windows frame the landscape, while clean architectural lines and warm finishes create a refined yet relaxed atmosphere. Here, beach access is part of everyday life, not an occasion. Also ideally located near marinas, farm stands, wineries, golf courses, and a short drive to Greenport Village. This is a rare opportunity to own in one of the North Fork's most desirable and tightly held locations.

Set along one of East Marion's most coveted waterfront stretches, 875 & 785 The Strand present a rare opportunity to own a combined 1.07-acre coastal compound in an exceptionally private and tightly held location. Spanning two adjoining parcels, this offering delivers scale, flexibility, and long-term potential rarely found on the North Fork. Perched just above the shoreline and directly across from the Long Island Sound, the property captures the quiet luxury that defines East Marion-unspoiled, understated, and deeply connected to the water. 785 The Strand features a light-filled, two-story residence with four bedrooms and three baths, designed for seamless indoor-outdoor living. Expansive windows frame the surrounding landscape, while clean architectural lines and warm finishes create a relaxed yet refined atmosphere. An oversized pool, multiple deck areas, and two fireplaces anchor the home as both a private retreat and an exceptional entertaining space. The adjoining 875 The Strand adds an additional .51 acres, opening the door to a range of possibilities-expanded outdoor living, guest accommodations, or the creation of a true multi-generational estate. The compound, which abuts protected communally-owned Pebble Beach non-buildable parcels on the east and south sides, is buffered by mature landscaping, offering a level of privacy and separation that is increasingly rare this close to the water. Beach access is just moments from your door. Also ideally located near marinas, farm stands, wineries, golf courses and a short drive to Greenport Village. This is a rare opportunity to secure a significant landholding in one of the North Fork's most desirable waterfront corridors, offering the scale to enjoy today, and the flexibility to shape for years to come.

Rare 1.07-Acre Coastal Compound on The StrandnSet along one of East Marion's most coveted waterfront stretches, 875 & 785 The Strand present a rare opportunity to own a combined 1.07-acre coastal compound in an exceptionally private and tightly held location. Spanning two adjoining parcels, this offering delivers scale, flexibility, and long-term potential rarely found on the North Fork. Perched just above the shoreline and directly across from the Long Island Sound, the property captures the quiet luxury that defines East Marion-unspoiled, understated, and deeply connected to the water. 785 The Strand features a light-filled, two-story residence with four bedrooms and three baths, designed for seamless indoor-outdoor living. Expansive windows frame the surrounding landscape, while clean architectural lines and warm finishes create a relaxed yet refined atmosphere. An oversized pool, multiple deck areas, and two fireplaces anchor the home as both a private retreat and an exceptional entertaining space. The adjoining 875 The Strand adds an additional .51 acres, opening the door to a range of possibilities-expanded outdoor living, guest accommodations, or the creation of a true multi-generational estate. The compound, which abuts protected communally-owned Pebble Beach non-buildable parcels on the east and south sides, is buffered by mature landscaping, offering a level of privacy and separation that is increasingly rare this close to the water. Beach access is just moments from your door. Also ideally located near marinas, farm stands, wineries, golf courses and a short drive to Greenport Village. This is a rare opportunity to secure a significant landholding in one of the North Fork's most desirable waterfront corridors, offering the scale to enjoy today, and the flexibility to shape for years to come.

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.

A Cinematic Waterfront Estate on Shelter Island, designed by acclaimed architect James Merrell. At the meeting point of sky and sea, this extraordinary contemporary waterfront retreat redefines island living. Designed to embrace panoramic views of Coecles Harbor and Gardiners Bay, the residence offers serenity, sophistication, and seamless indoor-outdoor connection - a rare combination on Shelter Island's coveted Little Ram peninsula. A discreet approach reveals a masterpiece with walls of glass, natural stone, and warm wood tones. Inside, expansive open living spaces capture the light and horizon from every angle. The main level flows effortlessly from the grand living area and gourmet kitchen to multiple terraces overlooking the water - perfect for entertaining or quiet reflection. 8 bedrooms, including a dramatic primary suite, ensure space and privacy for family and guests. Outdoors, a resort-like environment features a heated waterside pool, lush lawns, and a deep water dock for boating adventures across the Peconic and beyond. With its sophisticated architecture, cinematic setting, and direct access to the best of the Hamptons and Shelter Island, 8 Little Ram Island Drive offers a lifestyle that feels both secluded and world-class.

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.

Set in the heart of the historic district, this c.1890 Greenport Village gem boasts 3 bedrooms, 2.5 baths plus a detached studio apartment. It merges many distinctive original details with thoughtful modern updates. A beautifully planted enclosed rear garden with deck and patio, perfect for relaxing and entertaining, leads to a renovated barn which features a 2-car garage and the spacious studio apartment. The main residence's generous ground floor living spaces include a front parlor and living room with original pocket doors, dining room, powder room, and a large renovated kitchen centered on a 48' Capital gas range. Upstairs there are three bedrooms and two full bathrooms, including one en suite. Refinished original wood floors add warmth and character throughout. The restaurants, shops and waterfront of the maritime village are just a few blocks away from this refined and peaceful retreat. ID922412

Stunning Greenport New Construction Colonial w/ Heated In-ground pool! Step into a seamless blend of turn-of-the-century elegance and contemporary comfort in this exquisite new construction Colonial. Designed with classic architectural details and high-end finishes throughout, this 4-bedroom, 4.5-bathroom residence offers over 2,700 square feet of thoughtfully crafted living space and includes a 10x20 heated in-ground salt water pool. From the moment you arrive, the crushed stone driveway and detached 1-car garage set the tone for the timeless appeal of this home. Inside, you’ll find gleaming hardwood floors throughout, complemented by custom millwork that adds warmth and character to every room. The open floor plan is anchored by a spacious Great Room with a stately fireplace, creating a cozy yet sophisticated gathering space. The gourmet kitchen opens effortlessly to the dining and living areas, ideal for entertaining. The main-level primary suite is a serene retreat, featuring a spa-like en-suite bathroom and ample closet space. A charming laundry/mudroom with custom red brick flooring offers both function and style. Downstairs, the fully finished basement expands the living space with a second fireplace, a wet bar, a full bathroom, and a dedicated media room—perfect for movie nights or game-day entertaining. Enjoy outdoor living on the poolside private patio, ideal for morning coffee or summer barbecues. Every inch of this home reflects a perfect balance of traditional craftsmanship and modern convenience. A rare opportunity to own a new home with historic character in every detail that is in close proximity to Greenport Village, walk to 67 Steps Beach along the LI Sound and direct access to all that the North Fork has to offer!

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.

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.

Perched atop the bluffs of the Long Island Sound, this carefully designed showstopper is located within the desirable Eastern Stirling Shores community, offering private beach access just a short walk away. The rear yard provides a true resort-style setting, where you can bask in full sun poolside beside the natural gas–heated, in-ground saltwater pool with electric cover, all while enjoying exceptional privacy created by mature privet hedges surrounding the property. Inside, the home features beautiful white oak floors throughout and a stunning chef’s kitchen anchored by a dramatic waterfall stone island. The main level offers one of two primary en-suite bedrooms complete with dual walk-in closets, along with a full-size laundry room with sink, pantry, half bath, and multiple living spaces centered around a gas fireplace. The second floor features a second primary en-suite bedroom with a spacious walk-in closet, private bathroom, and a balcony capturing water views of the Long Island Sound. This level also includes an additional stacked laundry area and three more en-suite bedrooms, each with its own private bathroom and balcony access. Completing the home is a large attached two-car garage that flows seamlessly into the main living area, as well as a third garage located beneath the main level. A spacious walk-out basement with high ceilings offers the opportunity to easily finish over 1,000 additional square feet of living space. Offering an exceptional blend of location, amenities, and turnkey condition, this impressive home delivers the very best of North Fork coastal living.

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.

Dating back to the original 1871 layout of the Shelter Island Grove and Camp Meeting Association, Spring Garden Avenue is celebrated for its organic, rolling streetscapes and preserved 19th-century architecture. 5 Spring Garden Avenue is an authentic 1880 Victorian residence that embodies the classic style of the era, from its steeply pitched rooflines to its expansive exterior woodwork. The interior layout is expansive and true to its vintage, characterized by distinctive octagonal rooms on both the first and second floors. With five bedrooms, a sprawling third-floor attic loft, and a substantial footprint of covered decks and porches, the home offers a generous canvas within a historic setting. A significant structural update was completed in 2008, replacing the older foundation with a new poured concrete basement and structural footings, alongside the installation of a new roof. Featuring full access to the Shelter Island Heights Association tennis courts and beach club, this property represents an authentic piece of island history.