Greenport Real Estate

Welcome to Greenport, New York – a charming coastal village nestled in the heart of Suffolk County. Known for its picturesque waterfront views and vibrant community, Greenport is not just a great place to live; it also boasts an exceptional school district that prioritizes educational excellence.

The Greenport School District serves students from pre-kindergarten through high school, providing a nurturing environment that fosters both academic and personal growth. With a commitment to small class sizes, dedicated educators, and a diverse curriculum, the district ensures that each child receives the attention and resources they need to thrive. The schools are equipped with modern facilities and technology, enhancing the learning experience and preparing students for future success.

In addition to a strong academic foundation, Greenport School District emphasizes the importance of extracurricular activities. Students are encouraged to explore their interests through a variety of sports, arts, and clubs, promoting well-rounded development and community engagement. The district also values parental involvement, creating a collaborative atmosphere that strengthens the bond between families and schools.

Located just a stone's throw away from the scenic beaches and quaint shops of Greenport, families can enjoy a rich lifestyle that combines education and leisure. The community is known for its welcoming spirit, making it an ideal place for families to settle down and grow.

If you’re considering a move to Greenport, you’ll find not just a home but a supportive community and an outstanding educational environment for your children. Discover the charm of Greenport and the exceptional opportunities that await in its school district!

Newest Listings in Greenport

$945,000

3 Beds ⋅ 3 Baths ⋅ 1022960 MLS

Tucked away at on a quiet side street, this well-maintained East Marion residence offers a thoughtful layout and a peaceful setting just moments from everything the North Fork has to offer. Set on a generous half-acre parcel, the property provides ample outdoor space for entertaining, gardening, and recreation. Inside, the well-planned layout features three bedrooms and two-and-a-half baths, including a desirable first-floor primary suite that offers flexibility and convenience. The main living spaces flow comfortably while abundant natural light enhances the home's inviting atmosphere. An attached two-car garage adds valuable storage and functionality, while the quiet location enhances the home's sense of privacy. Ideally situated just moments from East Marion's beaches, farm stands, wineries, and the shops, restaurants, and waterfront of nearby Greenport Village, this home presents an exceptional opportunity to enjoy all that the North Fork has to offer.

345 Cemetery Road, East Marion

$949,000

2 Beds ⋅ 2 Baths ⋅ 1029495 MLS

Located in the sought-after Orient by the Sea community, this charming cottage is just a short walk 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

$1,785,000

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 Ninth Street Unit #43, Greenport

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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.