Refine Search
Map
Sort by
$699,000
2 Beds ⋅ 1 Baths ⋅ 1047466 MLS
Tucked away on one of the most coveted streets in Greenport Village, 216 Broad Street is a classic two-bedroom farmhouse just waiting for its next chapter to begin. If you’ve been dreaming of a creative project where you can build equity and put your personal stamp on a piece of North Fork history, this is the "diamond in the rough" you’ve been searching for. Stepping inside, you’re greeted by the warmth of original wood floors and the kind of architectural character that simply can't be replicated in new builds. The layout feels cozy yet functional, featuring a large pantry that offers incredible potential for a custom culinary space. Out front, the adorable porch is the perfect spot to sit with a morning coffee and soak in the breeze, while the expansive, private backyard serves as your own secret garden. The property even includes an accessory building—a blank canvas waiting for your imagination to turn it into a studio, workshop, or a unique garden retreat. Opportunities like this in the heart of Greenport are few and far between, so don't let this one slip away.

216 Broad Street, Greenport
$789,000
3 Beds ⋅ 2 Baths ⋅ 1043515 MLS
Opportunity knocks in Southold, one of the North Fork's most desirable locations. Bring your vision and unlock the potential of this well positioned home. Set on .60 acres, with room for a pool and just a short stroll from Southold Town Beach, this 3 bedroom, 2 bath home has good bones and offers the perfect foundation for a stunning North Fork transformation. Highlights include a dramatic sunken living room with vaulted ceilings and a wall of windows, a wood burning fireplace, dining area with access to a wrap-around rear deck, a main floor primary with ensuite, bonus room with closet, wet bar, sunroom, and walk-out basement offering a ton of potential and access to the garage. Hardwood flooring throughout the main level. While the kitchen and baths are original, the roof and electrical box are new and the home's appealing layout creates an exceptional opportunity for investors, renovators, or buyers seeking to create their dream North Fork retreat. Enjoy easy access to beaches, wineries, farm stands, marinas, and Greenport Village. Offered as-is.

455 Stony Shore Drive, Southold
$1,675,000
4 Beds ⋅ 3 Baths ⋅ 1047439 MLS
Located in the quaint town of East Marion this beautifully appointed ranch offers effortless one level living. Set on an acre property, bordering preserved land, this renovated home has been thoughtfully designed with four bedrooms, two of which are ensuite and three full bathrooms. Step inside to an open, light-filled layout where the kitchen flows seamlessly into inviting living room with fireplace and a dining room with vaulted ceiling. There is also a seamless flow between indoor and outdoor spaces-Step outside to a manicured yard with a Gunite heated saltwater pool, a serene private fenced backyard bordering preserved land - a peaceful and tranquil retreat-just moments to Rocky Point Beach, Greenport Village’s shops, restaurants, transportation and the North Fork’s best wineries and farm stands. This is North Fork living at its finest.

2737 Rocky Point Road, East Marion
$2,200,000
5 Beds ⋅ 4 Baths ⋅ 1043780 MLS
Immeasurable charm in the heart of Greenport Village. Beautifully updated while retaining much of its historic character, the main house features three bedrooms and three full baths, a handsome kitchen flooded with natural light, high ceilings, restored pocket doors, and original period moldings. At the rear of the property, a charming two-bedroom guest cottage with a full bath and kitchen provides wonderful flexibility for hosting or additional living and work space. Outside, the pool is tucked into beautifully established gardens, complemented by a bluestone patio and extensive mature landscaping that give the property a remarkable sense of privacy and place. All of this just moments from Greenport's downtown waterfront and some of the North Fork's best restaurants, shops, and waterfront destinations, with beaches, farm stands, and vineyards all within a mile.

611 1st Street, Greenport
$4,500,000
3 Beds ⋅ 2 Baths ⋅ 1047292 MLS
At the end of a secluded, private one-mile road, where the land meets the Long Island Sound, this newly renovated modern beach house offers breathtaking views, refined design, and total privacy. Set on two-thirds of an acre and surrounded by two 30 acre privately owned parcels of land, one of which is entirely vacant, the home features over 100 feet of private beachfront with a naturally sloped path leading to the shore. Every inch of this residence is bathed in natural light and designed to celebrate its stunning surroundings—from the expansive great room with white oak flooring and gas fireplace to the vaulted dining area and sleek kitchen with a gas stove and integrated workspace. The primary suite includes a spa-inspired bath with a sauna, shower, and bidet, while the additional first floor bedroom has an en-suite bathroom with a second floor bedroom as well. There is a full fitness center in a finished basement with heat and central air conditioning with walk out stairs to the pool area. All new Pella black-framed windows perfectly frame the Sound, with nearly every room offering unobstructed water views. Outside, lush landscaping and vibrant hydrangeas surround a 50’ x 8’ heated saltwater gunite pool with an automatic cover and stone patio, creating a peaceful outdoor retreat ideal for both entertaining and everyday living. The white board and batten siding, matte black metal roof, and detached one-car garage complete the clean, modern aesthetic. With porcelain tile sunroom floors, low taxes, and deeded road rights with private gate, this is a rare opportunity to own a fully renovated waterfront home with unrivaled serenity, where the sunsets, sea breeze, and silence feel like your own private oasis.

38099 Main Road, Orient
$864,200
3 Beds ⋅ 2 Baths ⋅ 1041851 MLS
Built in 1910, this classic Greenport Village farmhouse offers something that is becoming increasingly hard to find in the Village by having an extra wide, extra deep lot with the space to truly create the backyard lifestyle you have been wanting. With an outdoor fireplace under the stars, long summer dinners, gardens, entertaining space, and afternoons spent soaking up the sun before heading down to 6th Street Beach at the end of the road to cool off with the breeze off the water. Inside, the home retains original woodwork and that inviting farmhouse feel. With a surprisingly adaptable floor plan this house has an open layout. The front living room flows through the dining room and into the large farmhouse kitchen, creating a direct sightline all the way to the backyard. Morning light fills the kitchen, which opens naturally to the outdoor space and makes the yard a great space for outdoor dinners after having lunch at the beach. A generously sized bedroom on the main floor is in demand, while the second level offers an excellent opportunity to create a modern primary en-suite. That adaptability is one of the property's strongest features. Many homes from the early 1900s have floor plans that can be difficult to rework, but this home offers a layout and lot size that provide far more freedom to personalize and improve. Then there is the location. From here, Greenport Village is yours to enjoy, with easy access to the movie theater, IGA, restaurants, shops, Mitchell Park and Marina, the waterfront, and the energy that makes this Village such a special place. For someone who appreciates original character but wants the opportunity to create a home around today's lifestyle, this is an exciting chance to reimagine a classic Greenport farmhouse and make it entirely your own.

410 6th Street, Greenport
$2,250,000
3 Beds ⋅ 2 Baths ⋅ 1035595 MLS
Located in the heart of Orient Village, across the street from the Yacht Club and near all Village amenities, this fully updated nineteenth-century home features a wrap-around front porch, original hardwood floors, three bedrooms, first & second floor full baths, and a large eat-in kitchen with original pantry. The home has a front and rear staircase and a glass pocket door between the living room and formal dining room. A pathway leads through the rear garden to a two-story accessory structure of approximately 1,714 square feet, currently used as an artist's studio and art storage. The grounds are professionally landscaped with mature plantings, a dining patio, and multiple seating areas. Rarely does a property this unique come to market in Orient Village, the crown jewel of the North Fork.

1945 Village Lane, Orient
$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
$1,100,000
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
$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
$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
$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
2 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 façade, 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 equipped with electricity and water, and one including a bedroom — offer flexible space for guests, 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
$1,499,000
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
$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
$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
$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
$999,000
2 Beds ⋅ 1 Baths ⋅ 1017744 MLS
The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by. Located on a dead-end street on Hashamomuck Pond, this home offers a private dock, 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy boating, kayaking, paddleboarding, fishing, and swimming right out your back door. Surrounded by the gorgeous Southold beaches, over 40 wineries, and local farms, the North Fork has it all. Make it a vacation or year-round home, this is the lifestyle you have thought about, why not make it happen now!

136 Bayview Avenue, Southold
$5,695,000
4 Beds ⋅ 5 Baths ⋅ 1012436 MLS
Introducing a stunning waterfront estate on the Long Island Sound, now available for the first time from its original owners. This coastal gem, located in the North Fork, is situated in one of the most sought-after and picturesque areas on the East End. Nestled on nearly 2 acres, this 4,500 sq. ft. residence offers exceptional views and over 200 feet of private waterfront. The spacious open floor plan includes a junior primary ensuite on the first floor, featuring a separate entrance, a wrap-around covered porch, and direct access to the backyard. The gourmet kitchen is designed to capture breathtaking coastal views, boasting custom cabinetry, high-end appliances, beautiful granite countertops, and a spacious island with seating. Al fresco dining is made easy through the breezeway, which leads to the inviting patio and outdoor decks. The living room and dining room, enhanced by a central fireplace, are filled with natural light and feature beautiful wood floors. Tucked behind the fireplace and accessed through sliding barn doors, the home office offers water views and separate access to the yard. Upstairs, the primary bedroom features a balcony and an ensuite bathroom, showcasing stunning views. Additional bedrooms with balconies, a full bathroom, and a bonus space ensure privacy and comfort for guests. An oversized lounge, also with a waterside balcony and fireplace, connects to the kitchen below via a private staircase, creating an ideal space for a quiet retreat. The spacious art studio, built as part of the expansion, has cork flooring and a wall of windows overlooking the outdoor entertaining space, which includes a fully equipped custom kitchen, dining area, stunning pool, and spa amenities. The yard's mature landscaping and expansive lawn create a welcoming atmosphere for gatherings, with curated spaces for relaxation, including Adirondack chairs nestled along the coastline to enjoy the breathtaking sunsets. Additional amenities include an attached garage, greenhouse, a full unfinished basement with side yard access, and a generator. This property is conveniently located near Greenport Village, wineries, farms, and the bucolic landscape that exemplifies the essence of the North Fork region.

160 Sound Drive, Greenport
$929,000
1 Beds ⋅ 1 Baths ⋅ 1004839 MLS
Charming Cedar Shake Cottage on a Desirable Corner Lot. Enjoy it Now, and/or Expand Extensively in the Future with Proper Permits. The Spacious Deck, Brick Patio, Mature Landscaping, and Lush Shrubbery Create a Private and Secluded Backyard Retreat. Just 3–4 blocks to Beautiful Bay Beaches and 6 Blocks to Greenport Village, Marina, Shops, Restaurants, and NYC Transportation. Start Living the Good Life in Greenport Now. 1100 7th Street, Greenport is also known as 702 Linnet Street, Greenport.

1100 (aka 702 Linnett) 7th Street, Greenport
$4,250,000
4 Beds ⋅ 5 Baths ⋅ 1007919 MLS
Orient, North Fork - For buyers ready to trade city noise for salt air, open sky, and space to truly exhale, 1640 Grand View Drive in Orient offers the kind of North Fork escape that feels both elevated and completely livable. Set above the shoreline with sweeping, cinematic views over Long Island Sound, this Nantucket-inspired coastal estate combines privacy, scale, craftsmanship, and direct waterfront beauty in one rare offering. With approximately 130 feet of private beach and more than 5,000 square feet of upscale, finely crafted living space, the home is designed around what city life often lacks: light, quiet, room to gather, room to work, and a constant connection to nature. From nearly every living area, the setting frames wide-open views of water, sky, and shoreline, creating an everyday backdrop that feels more like a retreat than a residence. A spacious covered porch entry opens to a gracious foyer and sets the tone for the home’s relaxed coastal character. The dramatic living room, with soaring vaulted ceilings, clerestory windows, and expansive Long Island Sound views, is made for both slow weekends and effortless entertaining. It is the kind of room that can host a holiday dinner, a laid-back summer gathering, or a quiet night in with multiple fireplaces, a record playing, and the water just beyond the glass. The large dining room offers an elegant setting for dinners with friends and family, while the immaculate kitchen with breakfast area overlooks the lush landscape of this private coastal retreat. The open-plan family room, complete with a gas fireplace, flows naturally to the waterside terrace, blurring the line between indoors and out. Morning coffee, golden-hour cocktails, long summer lunches, and late-night conversations all find their place here, with the Sound as the view. The main level includes a thoughtfully designed owner’s suite with fireplace, sunroom/sitting room, and serene private spaces that make the most of the home’s waterfront orientation. A dedicated home office with private en suite bath adds the flexibility modern buyers want, whether used as a true work-from-home setup, creative studio, guest suite, or potentially a fifth bedroom. Upstairs, the home continues to offer room for everyone and everything: a large sitting room, billiard/family room, sewing or craft room, junior owner’s suite with full bath, and two additional bedrooms connected by a Jack-and-Jill bath. The layout is ideal for hosting weekend guests, extended family, or friends escaping the city or a hectic life for beach days, dinners outside, and slower mornings. Immaculate and exceptionally well-maintained, the estate includes a wine cellar, full-house generator, outdoor shower, and many quality details throughout. The grounds also offer room for a waterside pool (permits required), adding the possibility of creating a full resort-style experience at home. For buyers looking for a more grounded way to live without sacrificing style, comfort, or design, 1640 Grand View Drive offers a rare balance: sophisticated coastal architecture, true privacy, direct beach access, and the natural beauty of the North Fork. It is a place to host, recharge, work remotely, spend summers, or simply step into a quieter rhythm of life.

1640 Grandview 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.