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$999,000
3 Beds ⋅ 2 Baths ⋅ 1044713 MLS
Set in the wonderful North Fork beach community of Summit Estates, this spacious 3 bedroom, 2-bath cedar shake expanded ranch is ideal with its single-story living design and large yard ~ perfect for a pool and poolhouse. The Community beach, park, and dock are down an elegant private lane to a community parking lot and a magical paved trail. So handy to easily transport your beach and boat equipment from car to beach and boat! Close to Island’s End Golf Course, wineries, and the transportation hub and shopping/dining in the historic seaport Village of Greenport. A lovely North Fork retreat!

280 Marina Lane, East Marion
$1,595,000
6 Beds ⋅ 2 Baths ⋅ 1043177 MLS
Introducing an exceptional opportunity to own a truly turnkey, fully restored farmhouse-style two-family home in a prime Greenport Village location. 430 First Street features two meticulously updated residences, each offering three bedrooms, one full bathroom, and thoughtfully designed living spaces. The upper-level residence encompasses approximately 850 square feet and features soaring vaulted ceilings with decorative cross beams and an open-concept Great Room seamlessly connecting the kitchen, dining, and living areas. Three generously sized bedrooms, a full bathroom, and an in-unit washer and dryer complete the space. The main-level residence offers a similar layout with approximately 870 square feet of living space. Highlights include three bedrooms, one full bathroom, a spacious kitchen with vaulted ceilings, and separated living room, providing added flexibility and room to spread out. Outside, the property is equally impressive, with meticulously maintained landscaping, a newly installed crushed-stone driveway with Belgian block edging, a large rear lawn, full irrigation, and a charming front porch. A substantial 450-square-foot, two-car garage and additional storage shed further enhance the property's functionality. Whether you're an investor seeking a ready-made income-producing property or an end user looking to offset carrying costs with rental income, 430 First Street presents a compelling opportunity in the heart of Greenport Village. Located just two blocks from Greenport's vibrant business district, the property offers convenient access to public transportation, shops, restaurants, grocery stores, local farm stands, parks, and beaches—all while providing the space, condition, and versatility that make this a truly special offering.

430 1st Street, Greenport
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 1040676 MLS
What stands out about this home is how established and inviting it already feels. Mature trees and thoughtful landscaping surround the property, creating a beautiful setting from the moment you arrive. The covered front porch is a perfect place to sit and take in the changing colors of spring and summer, including the striking blue blossoms of the mature Vitex that become a highlight of the landscape each season. Inside, the home has an easy, open flow with wood floors, a spacious hallway leading to the bedrooms, and a living room and kitchen that connect naturally for everyday living and entertaining. Just off the garage, the laundry room and mudroom create a practical drop zone for shoes, bags, beach gear and everything else that helps keep the main living spaces organized. The fenced backyard has its own personality, with an outdoor fire pit, established vegetable gardens, a huge fig tree and an additional garden shed for tools, bikes and outdoor storage. It is the kind of yard that already feels lived in, cared for and ready to enjoy. Location adds another layer to the lifestyle. Iconic 67 Steps Beach is within walking distance for those incredible sunsets over Long Island Sound, while Greenport's coffee shops, restaurants and village destinations are close enough that grabbing your morning coffee does not always have to involve getting in the car. It is a home that combines comfortable everyday living with gardens, outdoor spaces and one of the things that makes Greenport so special: the ability to enjoy the beach, the village and the North Fork lifestyle right outside your door.

435 Sound Road, Greenport
$599,000
2 Beds ⋅ 2 Baths ⋅ 1038348 MLS
Welcome to easy North Fork living in Pheasant Run. This spacious 2-bedroom, 2-bath condominium offers a comfortable single-level layout with vaulted ceilings and abundant natural light. The home features a bright kitchen with ample cabinetry, a dining area with built-in window seating, and a generous living room with direct access to the rear deck and lawn. The primary bedroom includes a private full bath, while a second bedroom and full bath provide flexibility for guests or a home office. A full basement offers substantial storage and additional possibilities. Enjoy central air, a private outdoor space, and the ease of condominium living, all just minutes from Greenport Village, beaches, wineries, restaurants, shopping, and everything the North Fork has to offer.

1235 Calebs Way Unit #G25, Greenport
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 1039485 MLS
Classic Georgian Colonial set on approximately 0.47 acres, enhanced by mature spruce trees that offer natural privacy. The first floor features a welcoming living room with brick fireplace, formal dining room, family room, eat-in kitchen, conveniently located powder room, and access to the one-car garage. Upstairs are three bedrooms, including a spacious primary suite with private bath and large walk-in closet, plus two additional bedrooms sharing a full hall bath. A full basement with a separate entrance provides additional space and flexibility. A wonderful opportunity offering a traditional layout, generous property, and timeless Colonial character.

515 The Greenway, East Marion
$3,250,000
3 Beds ⋅ 2 Baths ⋅ 1038472 MLS
There are houses with water views, and then there are houses where the water is the whole point. Located in a waterfront beach community with tennis and pickleball, 380 The Strand delivers the rare North Fork combination of waterfront, an elegant renovation, community amenities, and a setting that feels quietly removed from the world-while still being exactly where you want to be. Picture perfect with the kind of wide-open sunset views that make dinner plans feel beside the point. Lovingly reimagined and offered turnkey, it has the ease of a summer house with the finish and comfort to make it very hard to leave in September. The interiors are fresh, warm, and thoughtfully done-nothing fussy, nothing to "fix". Just arrive, unpack, and settle into the rhythm of the North Fork. A garage adds welcome practicality, while the property offers room for a pool should one feel inclined to make a very good thing even better.

380 The Strand, East Marion
$1,175,000
4 Beds ⋅ 3 Baths ⋅ 1037504 MLS
Pool, private beach access and the North Fork lifestyle—all in one Greenport property. Set on approximately one-third acre, this spacious Cape offers 4 bedrooms, 2 full baths and approximately 2,400 square feet of above-grade living space, surrounded by mature landscaping and exceptional outdoor amenities. The private backyard is designed for summer living and entertaining, centered around an in-ground swimming pool, expansive outdoor areas and a secluded firepit setting. Just beyond home, enjoy private community beach access (Sterling Eastern Shores)—an increasingly rare amenity and the perfect setting for swimming, relaxing by the water and unforgettable Greenport sunsets. Inside, generous living spaces include a fireplace living room, separate den, open kitchen and dining areas, large bedrooms, first-floor laundry and flexible home-office space. The layout provides room to gather as well as plenty of space to spread out. A substantial finished lower level with separate exterior entrance provides additional flexible-use space, including laundry, a renovated bath and additional finished rooms. An oversized workshop adds even more versatility for hobbies, projects and storage. Whether you’re looking for a year-round North Fork home or a weekend retreat, this home offers a combination that’s difficult to duplicate space, privacy, a swimming pool, private beach access and the Greenport lifestyle.

130 Tasker Lane, Greenport
$1,395,000
3 Beds ⋅ 3 Baths ⋅ 1036264 MLS
Orient-by-the-Sea - Exceptional North Fork Living-Located within the sought-after soundfront community of Orient-by-the-Sea, this meticulously maintained Nantucket-style farmhouse offers the ideal blend of comfort, privacy, and charm. Residents enjoy access to a deeded association beach and park, complete with a stone path and picnic area just around the corner. A covered mahogany wraparound porch welcomes you into a bright, open interior filled with natural light. Gleaming wood floors enhance the living room with gas fireplace, while the dining room opens to a spacious 465-square-foot deck - perfect for outdoor dining and entertaining. The inviting kitchen features stainless steel appliances and a delightful breakfast nook. The first-floor primary suite offers direct porch access and a generous private bathroom with a walk-in shower and soaking tub. A laundry room and powder room complete the main level. A separate staircase leads to a spacious great room, ideal for gathering with family and friends, working from home, or creating a flexible recreation space. Upstairs are two comfortable guest bedrooms and a full bathroom. Additional feature includes an attached two-car garage. The full basement adds to the storage space and allows for potential future expansion of the living space. Set on nearly an acre, the level property offers a serene landscape with sweeping lawn, mature specimen plantings, abundant privacy, and ample room for a swimming pool. The Cross Sound Ferry, Orient Beach State Park, and Duryea's Orient Point are all nearby. A rare opportunity to enjoy year-round or seasonal living in one of Orient's most coveted North Fork communities.

870 Parkview Lane, Orient
$629,900
1038007 MLS
Welcome to 400 Aquaview Ave, East Marion, a rare opportunity to create your own North Fork retreat in desirable East Marion. Situated on approximately 0.56 acres, this vacant parcel offers a wonderful setting for those looking to establish a home in one of the East End’s most charming coastal communities. The lot sits around 150ft x 175ft affording ample space for a generous sized home, pool and outdoor entertainment space. The property fronts Aquaview Ave but also extends to Circle Dr W for if creating a nice private drive is in your vision. Surrounded by the natural beauty and relaxed atmosphere that define the North Fork, the property provides an exciting opportunity to bring your dream home to life. Just a short walk away you'll find access to sound beaches at the top of Rocky Point Road, Kontokosta Winery, Greenport Village, Orient Point Ferry and all the beauties of the North Fork.

400 Aquaview Avenue, East Marion
$825,000
3 Beds ⋅ 2 Baths ⋅ 1037952 MLS
Charming Greenport Village Getaway Enjoy the best of the North Fork from this inviting 3-bedroom, 2-bath home, perfectly located near all that Greenport Village has to offer. Stroll to Mitchell Park, waterfront dining, restaurants, shops, and the Shelter Island Ferry, or spend the day exploring nearby vineyards and Greenport Harbor Brewing Company. A wonderful opportunity to enjoy the relaxed charm, walkability, and vibrant lifestyle of Greenport Village—close to everything, yet your own peaceful retreat.

429 Kaplan Avenue, Greenport
$799,000
2 Beds ⋅ 2 Baths ⋅ 1036090 MLS
Enjoy Exceptional Water Views from this Second-Floor, 2-Bedroom, 2-Bath Condominium Featuring a Spacious Storage Loft and Private Deck Overlooking the Waterside Lawn and Bay. Cleaves Point Condominium Is Beautifully Situated on 13 Waterfront Acres at the End of Shipyard Lane in East Marion. Community Amenities Include a Private Bay Beach, Marina with Docking, Swimming Pool, Clubhouse with Gym, Tennis, Pickleball, Basketball, Community Garden, and More. Conveniently Located Near Island’s End Golf, Greenport Village, and All That the North Fork Has to Offer. Low Taxes Further Enhance This Outstanding Opportunity. Estate Sale. Sold “As Is”.

2820 Shipyard Lane Unit #1B2, East Marion
$950,000
2 Beds ⋅ 2 Baths ⋅ 1035706 MLS
Orient By The Sea —North Fork living at Its Best- Located in the sought-after Orient By-The-Sea community, this charming two-bedroom, two-bath expanded ranch offers the ease of one-level living on a private, level, shy-acre property. With a deeded association beach and park just around the corner, this is a wonderful opportunity for both year-round and vacation living. The spacious, light-filled great room is the center of the home, with doors opening to an expansive patio with a retractable electric awning. Designed for outdoor living and entertaining, this inviting space overlooks the landscaped, park-like grounds and offers ample room for a swimming pool. The interior features two bedrooms and two full baths, including one with a generously sized walk-in shower. Additional living spaces include a welcoming dining room, comfortable living room, updated kitchen with a breakfast nook, and convenient laundry access. The home’s easy layout and abundance of natural light create a warm and inviting atmosphere throughout. The 1-car garage offers space for storage or future expansion. Enjoy all that Orient and the North Fork have to offer, with the Cross Sound Ferry, Orient State Park, and Duryea’s Restaurant just minutes away. The beautifully maintained association sound beach is a neighborhood treasure, featuring a stone path and picnic area, perfect for relaxing by the water, gathering with friends and family, and enjoying spectacular North Fork sunsets. A special opportunity to live, relax, and enjoy the North Fork lifestyle in one of Orient’s most desirable communities.

395 Uhl Lane, Orient
$799,000
1 Beds ⋅ 1 Baths ⋅ 1035656 MLS
A rare opportunity to own an early 20th-century Adirondack-style cottage in Greenport, ideally situated just 0.12 miles from a beautiful Sound beach and only one mile from the heart of Greenport Village. This charming cottage showcases many of the home’s original details starting with a screened-in front porch spanning the full width of the facade, creating a welcoming indoor/outdoor retreat. Inside, the open floor plan includes a living/dining room with a wood-burning stove, an eat-in kitchen, full bath, laundry, and access to a rear deck. The second floor offers a cozy loft-style bedroom. Two additional accessory structures, each with electricity and water, provide flexible space for a home office, studio, or creative workspace. Surrounded by trees creating privacy and offering open vineyard views, this distinctive cottage compound captures the relaxed character and timeless appeal of the North Fork.

44 (1180) Sound Road, Greenport
$1,699,999
4 Beds ⋅ 3 Baths ⋅ 1029031 MLS
Steeped in the history of Orient, this exceptional Craftsman-style residence occupies a remarkable setting along historic Main Road, once known as King’s Highway, directly across from the entrance to Orient Beach State Park. Originally purchased by a member of the pioneering Latham farming family, the home was thoughtfully expanded in the 1920s with the addition of its signature wide front porch and interior improvements. In 1938, the family donated the land across the street that would become the entrance to today’s Orient Beach State Park, forever connecting this property to one of the North Fork’s most treasured destinations. Architecturally, the home showcases timeless Craftsman character with distinctive three part windows across the front facade, each crowned with elegant lozenge paned transoms. The welcoming front entrance, framed by classic sidelights, opens to interiors where original woodwork, period doors, and handcrafted details remain beautifully intact. Modern updates to the large country kitchen, bathrooms, natural gas heating, and central air provide today’s comforts while preserving the home’s historic integrity. The property’s story extends beyond the main residence. A historic building from the famed Orient Point Inn, a resort established in 1672, was relocated to the backyard in the early twentieth century. Once serving as the inn’s men’s rooms and kitchen building, it now anchors the grounds as a fascinating reminder of Orient’s maritime heritage. Life here is defined by both history and location. Relax on the expansive front porch where seasonal water views, cool coastal breezes, and the distant sound of ferry horns create an unmistakable North Fork atmosphere. The original wood-burning fireplace, gracious front and rear staircases, and oversized country kitchen invite gatherings both large and small. Protected open space bordering one side of the property, paired with a classic neighboring farmhouse and historic barn on the other, preserves the peaceful character that has defined Orient for generations. Just moments away are Orient Beach State Park, Duryea’s Marina and Restaurant, the Cross Sound Ferry, and Orient Point County Park with its iconic lighthouse. Whether exploring by bicycle, spending the day on the beach, or simply enjoying the quiet rhythm of this waterfront community with some of the best fishing off of Plum Gut, every day feels connected to the rich history and natural beauty that make Orient one of Long Island’s most treasured destinations. This is more than a historic home. It is an opportunity to become the next steward of a property that has helped shape the story of Orient for generations

40495 Main Road, Orient
$949,000
2 Beds ⋅ 2 Baths ⋅ 1029495 MLS
Located in the sought-after Orient by the Sea community, this charming ranch is just .3 miles from the Association Sound Beach. The .437-acre property includes a spacious fenced backyard with mature specimen trees and three sheds. Interior highlights include an exposed-beam living room ceiling, solid hardwood doors and cabinets, oak and tile floors, a wood-burning stove, and an updated kitchen. Enjoy one floor living in this well-built home.

700 Plum Island Lane, Orient
$2,249,000
4 Beds ⋅ 4 Baths ⋅ 1032350 MLS
Welcome to this exceptional estate, just a short walk from a private deeded beach and dock. Designed for entertaining, this spacious property features an impressive outdoor living area complete with a covered, built-in bar and kitchen—perfect for hosting family and friends. Enjoy the quiet, peaceful surroundings while still being close to everything you need. With low taxes and move-in-ready condition, this home offers the ideal combination of comfort and convenience. Furniture is negotiable, and the property may be sold furnished.

705 Gus Drive, East Marion
$1,800,000
1008060 MLS
2.03 acres of prime real estate on route 25 in Greenport. Property is currently improved with a 1 story, 2 bedroom house and is zoned for Light Industrial. LOW yearly taxes. Schedule your showing now!

69430 Main Road, Greenport
$1,499,000
3 Beds ⋅ 2 Baths ⋅ 1031857 MLS
Experience waterfront living at its finest, in this exceptional cottage located directly on the Bay. This turn-key, one of a kind property, offers gorgeous water views and open concept living. The dramatic vaulted ceilings with exposed beams, create a stunning focal point, adding warmth, texture, and character throughout the living space. Step outside to your own private beach; perfect for swimming, kayaking, paddle boarding, boating, entertaining, or simply relaxing with your feet in the sand. The panoramic views create an unmatched open-bay lifestyle. Wake up each morning to the soothing sounds of the bay and breathtaking sunrises over the water, just steps from your door. This 3 bed 1.5 bath is waiting for you. Located in peaceful East Marion, this home has close proximity to the Jitney, LIRR, amazing restaurants, and the best vineyards the North Fork has to offer. Simply arrive, unwind, and enjoy the waterfront lifestyle you've been dreaming of.

80 Rabbit Lane, East Marion
$795,000
1026672 MLS
Life's better on the sound! This sound-front lot boasts 50’ of waterfront and approved plans for a 3-bedroom, 2-bath home. Imagine mornings on the porch, afternoons on the water, and evenings with a front-row seat to the most spectacular sunsets around. Whether you're building your forever home, a weekend retreat, or an investment property, this lot is ready when you are and offers the best of North Fork living—just minutes from beautiful beaches, award-winning vineyards, marinas, renowned restaurants, farm stands, boutique shopping.

55915 County Road 48, Greenport
$8,400,000
6 Beds ⋅ 7 Baths ⋅ 964447 MLS
Rare opportunity to own a uniquely private 7.49-acre bay front estate in Orient Village. This exceptional waterfront property features a spacious 5700 sq ft main residence with 6 bedrooms, 7 baths, three wood burning fireplaces, three bay garage, expansive front and rear covered porches and panoramic bay views. The 20 x 44 heated pool is complemented with a 860 sq ft pool house featuring open common area, kitchenette, full bath, laundry, two changing rooms, outdoor shower, & porch – creating an ideal setting for entertaining and summer living. A fully fenced clay 60 x 120 ft tennis court is expertly sited, so sun glare is never an issue. The property offers an additional free-standing two-bay garage with second floor bonus space providing flexible options for recreation, boat/bike storage or studio space. The 195 ft wide private walkout bay beach offers sweeping Harbor views of Long Beach State Park, Bug Light House and Orient Yacht Club. The property is ideally located within walking or biking distance to the Village of Orient, Orient Yacht Club, local marinas, Post Office, the Country Store, Oysterponds Historical Society and all village amenities.

1600 King Street, Orient
$799,000
3 Beds ⋅ 1 Baths ⋅ 1028101 MLS
Super Cute Greenport Village home packed with charm and character. Walking distance to downtown. 3 bedrooms, 1 bath, diving area, kitchen and living area all on 1st floor with 3 bedrooms and a full bathroom above. Full walk out Basement and fenced in yard. Close to downtown Greenport, Marinas, Golf, restuarants and wineries.

308 Monsell Place, Greenport
$1,249,000
3 Beds ⋅ 4 Baths ⋅ 1028434 MLS
Stylish Heritage Farmhouse: Dating to approximately 1910, this beautifully reimagined Queen Anne–inspired country home preserves a tangible connection to East Marion’s past. Set along the historic route once known as Kings Highway and Sunset Trail—today’s Main Road—and near Marion Lake, the residence was built when the hamlet still reflected its longstanding agricultural and maritime heritage while emerging as a sought-after North Fork summer retreat. Comprehensively renewed for contemporary living, the home pairs early-20th-century character and gracious proportions with refined interiors and exceptional outdoor potential. All major systems have been updated, offering the comfort, convenience and confidence of a modern residence within a home of enduring character. Privately situated behind stylish gates on a level, sun-filled half-acre, the property offers turnkey living in a thoughtfully landscaped setting. A welcoming wraparound porch opens to a beautifully appointed kitchen featuring stainless-steel appliances, quality finishes and sophisticated details. The open-concept living and dining areas flow naturally from the kitchen and extend to an open-air deck overlooking the expansive backyard. An existing pool permit provides an exciting opportunity to create a private outdoor retreat, while one of the property’s two substantial sheds could potentially be converted into a pool house, subject to applicable permits and approvals. The first-floor primary suite includes a beautifully finished bath with a soaking tub, while a separate powder room serves guests. Upstairs, two additional en-suite bedrooms each feature a thoughtfully designed full bath. Generous proportions continue throughout the home, with the basement providing abundant storage and a spacious laundry room. Propane heat and new central air conditioning ensure year-round comfort. The home’s flexible layout and peaceful yet convenient location also create an ideal live-work environment for remote professionals, digital nomads and those seeking a sophisticated country escape without sacrificing modern connectivity or convenience. Low East Marion taxes, two large sheds and mature landscaping further distinguish the offering. Ideally located minutes from Long Island Sound and Peconic Bay beaches, Marion Lake for kayaking and birdwatching, and the shops, restaurants and waterfront attractions of Greenport Village—with ferry connections to Shelter Island and the Hamptons—this stylish heritage farmhouse presents a rare opportunity to embrace four-season North Fork living and establish your own enduring North Fork legacy.

East Marion
$1,695,000
4 Beds ⋅ 3 Baths ⋅ 1027434 MLS
Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings, an elegant open staircase, and an inviting sense of scale that sets the tone for the home's thoughtfully designed interior. The main level offers an exceptional layout for both everyday living and entertaining, featuring a formal dining room, gracious living room, and an inviting media room anchored by a classic wood-burning fireplace. At the heart of the home, the spacious eat-in kitchen is appointed with abundant cabinetry, generous counter space, and a highly functional layout designed to accommodate everything from casual everyday meals to large-scale gatherings. Just beyond, a private home office overlooks the rear grounds, providing a peaceful and inspiring workspace. Occupying nearly 900 square feet, the second-floor primary suite serves as a true private retreat, complete with dual custom walk-in closets and a luxurious spa-inspired bath featuring double vanities, a walk-in shower, and a Jacuzzi soaking tub. Three additional guest bedrooms and a well-appointed full hallway bathroom complete the upper level, providing comfortable accommodations for family and guests alike. Another huge bonus is the expansive unfinished basement with 8' ceilings and walk-out egress already in place, making this ripe for another fully finished space which would add approximately 1400 additional sqft. Perfectly positioned within one of Greenport's most desirable beach communities, residents enjoy private access to the Rock Cove Estates association beach while remaining just minutes from the vibrant shops, acclaimed restaurants, marinas, and waterfront attractions of Greenport Village, as well as the renowned wineries, farm stands, and scenic beauty that define the North Fork lifestyle.

90 Caiola Court, Greenport
$6,000,000
3 Beds ⋅ 3 Baths ⋅ 1015950 MLS
Set on 9.1 remarkably private acres in one of Orient's most scenic and protected landscapes, this distinctive residence offers a rare combination of architectural character, beautifully developed grounds, and sweeping pastoral views across meadows, Hallock Bay, and Gardiners Bay beyond. Originally part of the historic Hallock farm, the property has been thoughtfully cultivated over decades. Specimen trees, extensive landscaping, and a pond create a setting that feels both intentional and deeply connected to the surrounding natural environment. The elevated position captures expansive vistas while preserving a remarkable sense of privacy. The cedar-clad home was designed to maximize natural light and take full advantage of its extraordinary surroundings. Floor-to-ceiling windows frame the landscape, while more than 1,000 square feet of porches and decking create a seamless relationship between indoor and outdoor living. Classical proportions are balanced by a contemporary coastal sensibility, resulting in a residence that feels timeless, comfortable, and distinctly North Fork. Outdoor amenities are equally compelling. A large gunite pool is set within a bluestone surround and complemented by a brick patio and pergola-covered terrace. The accessory building immediately adjacent incorporates a pool house, substantial loft space, and a two-car garage, providing flexibility for storage, recreation, or studio use. Located within the coveted Narrow River corridor, the property offers easy access to quiet beaches, exceptional wildlife viewing, and the marina, while remaining moments from Orient Village. Properties of this scale and setting rarely come to market, particularly in a location where protected landscapes and enduring views define long-term value.

4725 Orchard Street, Orient
$295,000
1 Beds ⋅ 1 Baths ⋅ 1026077 MLS
Enjoy easy living in this 1-bedroom, 1-bath co-op, located just a short walk from the charming Village of Greenport. This move-in-ready home features a newly updated kitchen with modern appliances, a renovated bathroom, and fresh finishes throughout. Perfectly situated to enjoy everything the North Fork has to offer, you'll be just minutes from beautiful beaches, award winning wineries, boutique shopping, restaurants and waterfront attractions.

1000 9th Street Unit #43, Greenport
$1,375,000
3 Beds ⋅ 2 Baths ⋅ 1024020 MLS
Perfectly positioned between Greenport and Southold, this classic cedar-shingled Cape offers an easygoing North Fork lifestyle with beaches, restaurants, and village amenities just minutes away. Inside, the first-floor open plan is anchored by a fireplace and a large kitchen flooded with natural light. Multiple sliding doors lead to a generous wraparound deck, outfitted for dining, lounging, and entertaining. An expanded second floor is devoted to a spacious primary suite with seperate office and a large ensuite bathroom. The backyard invites summer afternoons around the bocce court, and peekaboo water views across the street subtly remind of the home's coastal setting. A full basement provides great utility and flexibility. Comfortable, stylish, unpretentious, and exceptionally well-located, this home is as well-suited to weekends as it is to everyday living.

1050 Bayview Avenue, Southold
$1,299,000
4 Beds ⋅ 2 Baths ⋅ 1021286 MLS
This storybook circa 1858 cottage captures the very essence of North Fork living: cozy, charming, and effortlessly inviting. Rich in history and timeless appeal, this beautifully preserved home blends the simplicity of a bygone era with thoughtful modern updates, creating a warm and welcoming retreat. Inside, random-width wide plank flooring adds authentic character throughout. The first floor offers a spacious primary bedroom, a second bedroom or home office, an inviting living room, formal dining room, and an eat-in kitchen with a convenient laundry area. Upstairs, two additional bedrooms and a half bath provide comfortable accommodations. Architectural details enhance the home's enduring charm, from the welcoming semi-wraparound covered front porch to the side deck with a new retractable awning overlooking beautifully landscaped gardens. A pergola with a slate patio creates the perfect setting for outdoor dining, entertaining, or simply relaxing on a summer evening. Adding to the property's appeal is a detached 2-car garage and a delightful artist's or hobby studio, complete with its own pergola-covered sitting area nestled among lush gardens. Privately tucked behind a classic white picket fence, the beautifully landscaped .5-acre property is an exceptional outdoor sanctuary. The backyard features a heated free-form Gunite pool with a cascading waterfall, a pool shed with deck, two additional storage sheds, mature trees, and an abundance of seasonal flowering plantings, creating a peaceful and private oasis. Ideally located just minutes from pristine beaches, golf courses, marinas, renowned wineries and breweries, county parks, farm stands, Hampton Jitney and popular local eateries. This special property also enjoys close proximity to Historic Greenport, where waterfront dining, boutique shopping, and galleries await. The backyard abuts a nature preserve that leads to Marion Lake County Park. Nothing can be built behind it. Whether you're enjoying a quiet morning coffee on the porch, spending the afternoon poolside, or entertaining friends after a day at the beach, this one-of-a-kind North Fork treasure offers the perfect blend of historic character, modern comfort, and relaxed coastal living.

8440 Main Road, East Marion
$1,899,999
1017889 MLS
Very near the eastern tip of Long Island’s renowned North Fork, this exceptional 1.37-acre beachfront property presents one of the few remaining opportunities to create a legacy waterfront estate in one of Orient’s most breathtaking coastal settings. Surrounded by panoramic views of Gardiners Bay, Long Island Sound, Plum Island, and the Connecticut shoreline, this remarkable homesite enjoys direct access to a sandy beach and the added distinction of neighboring protected Suffolk County parkland, preserving the natural beauty and open coastal landscape that define this extraordinary location. With approximately 125 feet of private beachfront, the property offers an ideal setting for relaxed coastal living and entertaining. The grounds provide ample space for hosting weekend guests, extended family, or friends escaping the city for beach days, outdoor dining, and slow, restorative mornings by the water. There is also the potential for a waterside pool (permits required), creating the opportunity to design a true resort-style coastal retreat. Wake to spectacular sunrises over Long Island Sound and embrace the quintessential North Fork lifestyle. Spend your days boating, kayaking, paddleboarding, fishing, swimming, beachcombing, or exploring the scenic trails and shoreline of nearby Orient Point County Park. Walk along the beach to take in views of the iconic Orient Point Lighthouse, affectionately known as the “Coffee Pot,” or take the nearby Cross Sound Ferry to New London for a day trip before returning home to the peace and privacy of your waterfront escape. Just minutes away, enjoy the charm of Orient Village, award-winning North Fork vineyards, local farm stands, marinas, and the iconic Duryea’s, where waterfront lunches and unforgettable sunset dinners are part of everyday life. For buyers seeking a more grounded way of living without sacrificing style, comfort, or design, this property offers a rare balance of sophistication, privacy, and direct beachfront access. It is a place to host, recharge, work remotely, spend summers, or simply step into a quieter rhythm of life. For city-area buyers ready to trade noise for salt air, open sky, and space to truly exhale, 1890 Lands End Road offers a rare North Fork escape that feels both elevated and effortlessly livable, where cinematic water views, natural beauty, and true coastal privacy come together in one extraordinary offering.

1890 Lands End Road, Orient Point
$2,795,000
5 Beds ⋅ 5 Baths ⋅ 1018538 MLS
Set on 2.3 private acres just off one of the North Fork's most desirable waterfront streets, this brand-new cedar-shingled residence offers timeless design, generous proportions, and an enviable combination of privacy and convenience. Spanning three finished levels, the home features five bedrooms and five baths, with thoughtfully designed living spaces that balance everyday comfort with an optimal footprint for entertaining. Outside, a gunite pool is positioned within the expansive grounds, creating a private retreat surrounded by mature landscaping. The prime location is just a few hundred yards from Sound beach access and less than five minutes from Greenport Village and Orient's Village Lane. With acclaimed restaurants, marinas, farm stands, wineries, and golf all minutes away, you have incredible access while maintaining the peace and privacy that make this corner of the North Fork so special.

205 Kats Court, East Marion
$2,100,000
1019090 MLS
Build your North Fork Sanctuary on the Sound. This is your opportunity to bypass years of time in the application process. Trustees approval already in place allowing a magnificent 2 story Custom Built home with expansive decks and outdoor spaces and a waterside pool overlooking the Sound. A low bluff with just enough elevation and natural steps to the beach located in a cove allows protection and privacy. Just imagine yourself enjoying the quiet days taking in this spectacular view in the home you have always envisioned escaping to on the North Fork. Floor Plans and Site plan available. Contact Agent

75 Pettys Drive, Orient

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.