Greenport Real Estate

Welcome to Greenport, NY – a charming village nestled in the heart of Suffolk County, where picturesque views meet a vibrant community and an exceptional school district. Greenport is not just a beautiful coastal destination; it’s also home to the Greenport Union Free School District, renowned for its commitment to academic excellence and holistic student development.

The Greenport School District serves a tight-knit community, providing personalized attention to each student. With small class sizes and dedicated educators, children receive the support they need to thrive both academically and socially. The district emphasizes a well-rounded education, offering a diverse curriculum that includes advanced placement courses, arts, and athletics, ensuring that every child can explore their passions and talents.

Parents can take comfort in knowing that Greenport schools prioritize not only academic achievements but also character development. Through various programs and community engagement initiatives, students learn the importance of collaboration, leadership, and civic responsibility. The district’s commitment to fostering a nurturing environment helps students build a strong foundation for their future.

Beyond academics, Greenport itself is a delightful place to live. Known for its charming waterfront, local vineyards, and rich maritime history, residents enjoy a blend of small-town charm and modern amenities. With easy access to beaches, parks, and recreational activities, families have plenty of opportunities to create lasting memories together.

Choosing Greenport means choosing a community that values education, growth, and a vibrant lifestyle. Discover the perfect place to plant your roots and watch your children flourish in this idyllic setting!

Newest Listings in Greenport

$1,350,000

4 Beds ⋅ 3 Baths ⋅ 1061683 MLS

This Traditional 4-bedroom, 2.5-bath home sits near Orient State Park and the Cross Sound Ferry. The private, landscaped backyard has a pool and patio, plus a large deck with glass doors to the open-plan kitchen and family room, making it ideal for entertaining. The first floor is completed with a private living room, a dining room, laundry, and a powder room. Upstairs, the primary ensuite has a full bath with views of the backyard and pool. Three more bedrooms and a full bath complete the second floor. The finished lower level offers a large recreation space. This home is ideal year-round living or for enjoying North Fork summers.

39595 Main Road, Orient

$749,000

1062908 MLS

Explore the possibilities at 320 Lands' End Road in Orient. This approximately 0.97-acre vacant parcel offers an opportunity to create a North Fork retreat, subject to all required approvals. Located in the Town of Southold and reported within the R-40 residential zoning district, the property provides space to explore a custom home design in this desirable East End setting. Buyers should independently verify zoning, permitted uses, buildability, utilities, septic requirements, and any environmental restrictions. All development is subject to applicable Town, County, and State approvals.

320 Lands End Road, Orient

$1,975,000

5 Beds ⋅ 2 Baths ⋅ 1056150 MLS

One of Greenport’s most iconic homes, the William Corey House was built circa 1882 and stands as a beautiful testament to the village’s rich maritime history. Built for William D. Corey of Webb & Corey, a prominent ship chandlery that supplied vessels passing through Greenport’s bustling harbor, this distinguished residence has a direct connection to the working waterfront that helped shape the village. Set on a generous double lot graced by magnificent mature beech trees and a charming carriage house, the residence is distinguished by its slate roof, scalloped shingles, and decorative brackets. A gracious wraparound porch framed by Ionic columns welcomes visitors, while a Colonial-style doorway with an arched transom and sidelights adds to its timeless appeal. Together, these beautifully preserved period details reflect the craftsmanship and prosperity of Greenport’s years as a thriving port. Long admired by residents and visitors alike, 440 1st Street represents a rare opportunity to own a meaningful piece of Greenport’s architectural and maritime heritage. Awaiting its next steward, this extraordinary property offers the chance to restore its beauty, honor its history, and write the next chapter of one of the village’s most recognizable homes.

440 1st Street, Greenport

$1,100,000

3 Beds ⋅ 2 Baths ⋅ 1040671 MLS

What caught my attention at 216 Monsell Place is how much of the original Greenport farmhouse feeling is still here, but the house has evolved into a layout that works really well today. You start with that wide wraparound porch. I can immediately picture sitting out there with coffee in the morning or having a drink at the end of the day. Then you walk inside and the pine floors, wood-burning fireplace and natural character remind you why these older North Fork homes are so appealing in the first place. The kitchen feels fresh and updated with new appliances, but what I really noticed was the light. There is a full-glass door at the side entrance, and in the afternoon the sunlight comes right into the kitchen. It gives the room a completely different feel and connects it visually with the backyard. Upstairs, there are three bedrooms, and one of them has some really interesting ceiling details that you just don't expect until you walk into the room. There are built-in closets, a second full bathroom, and another bright space with a great group of windows that I immediately thought would make an awesome home office. Then you walk outside and realize just how much yard there is. For Greenport Village, this is a really generous lot. You already have established trees and a great storage barn, but there is still plenty of space to have some fun with it. I can picture outdoor dining, gardens, a fire pit, lounge areas or simply a big backyard where everyone can spread out. And I like where it sits in the Village. Grab a bike and you can head over to Klipp's Park Beach, Smugglers Cove or Billy's By The Bay and spend an afternoon around the water and the marinas. For me, that's what makes this house interesting. A lot of the charm is already here, but there are still enough possibilities that you can start imagining what you would do with it.

216 Monsell Place, Greenport

$1,300,000

4 Beds ⋅ 2 Baths ⋅ 1058255 MLS

Welcome to 402 5th Street, a 4 bedroom, 2 full bathroom historic Victorian located in the heart of west Dublin on a double lot, with plenty of room for an in-ground pool and just 3 blocks to a sandy bay beach. The home is also zoned to be converted to a 2-family dwelling. The residence offers original wide plank flooring, a large back deck and private back yard with a large shed. On the first floor, a side entrance leads to a formal kitchen, dining room, den or reading area and living room with a colossal fireplace. The second floor primary bedroom has a cathedral ceiling with skylights and plentiful amounts of natural light. There are three additional bedrooms, a full bathroom and separate exterior staircase leading to the second floor. The home is located a few blocks from the heart of Greenport Village.

402 5th Street, Greenport

$1,990,000

4 Beds ⋅ 5 Baths ⋅ 1061404 MLS

Built in 2020, this 4-bedroom, 3.5-bath cedar-shingle home in East Marion pairs modern construction with extensive outdoor amenities, protected farmland views, and the Peconic Bay at the end of the street. Designed by landscape architects Marshall & Paetzel, the resort-style backyard features a 15x40 heated gunite pool with an electric cover and fiber-optic lighting, complemented by a private 5x15 foot spa with a soothing fountain and fully irrigated Zen garden. The custom poolside cabana offers motorized screens, a half bath, a bar with a sink, ice maker, and refrigerator, plus an outdoor shower that is served by its own tankless water heater. A 20x40 foot marble patio brings the outdoor entertaining space together with a built-in DCS grill and dedicated dining and lounging areas. Inside, a vaulted entry opens to the main level, where the dining room flows into the chef’s kitchen with an oversized island, Viking range, Sub-Zero refrigerator, Miele dishwasher, and wine refrigerator. The adjoining great room features built-in shelving and a marble-surround gas fireplace. The first-floor primary suite includes a walk-in closet and a double-vanity bath with an oversized shower. A laundry room, powder room, and two-car garage complete this level. Upstairs, a recently renovated second primary suite offers a private bath, lounge area, and walk-in closet. Two additional bedrooms, a shared bath, and a storage area complete the second level. The unfinished basement offers approximately 1,000 square feet with 9-foot ceilings and potential for future expansion. With thoughtfully designed spaces inside and out, this East Marion retreat offers a complete package, with golf, wineries, Greenport, and the North Fork's many other attractions just minutes away.

1165 Shipyard Lane, East Marion

$5,350,000

5 Beds ⋅ 5 Baths ⋅ 1059750 MLS

Perfectly positioned on a bluff overlooking the Long Island Sound, this Nantucket-style cedar-shingled home captures sweeping water views and spectacular sunsets from nearly every vantage point. Multiple waterside decks and balconies make the most of the setting, while a heated pool, outdoor kitchen, and stairs to a private beach create an exceptional environment for summer living and entertaining. Inside, beautifully appointed living spaces include en-suite bedrooms on both the first and second floors, offering flexibility for owners and guests alike. A finished lower level with a private theater provides additional space for recreation. Less than a mile from the heart of Greenport Village, this exceptional waterfront property combines coastal beauty, privacy, and proximity to one of the North Fork’s most desirable destinations.

1000 Sound Drive, Greenport

$1,890,000

3 Beds ⋅ 3 Baths ⋅ 1059854 MLS

Meticulously restored Craftsman on coveted Orchard Street in the heart of Orient Village. The private 0.55-acre lot offers an 18x40 heated in-ground pool, an original two-car garage and an outbuilding. A covered front porch opens to a welcoming foyer, which flows into a living room with a wood-burning fireplace and on to the dining room and eat-in kitchen. A mud room with laundry and a powder room complete the first floor. Upstairs is a primary suite with full bath and two additional bedrooms sharing a second full bath. Stroll to the village shops, country store, post office and yacht club, and enjoy the breezes off Orient Harbor.

845 Orchard Street, Orient

$840,000

1060295 MLS

Beautifully renovated historic building in the heart of Greenport Village’s commercial district. This light-filled, two-story property has been home to the well-established VSOP Projects art gallery for the past eight years and offers a versatile layout well-suited to a range of uses, presenting an exciting opportunity for its next entrepreneur or investor. Stunning original wide-plank floors and a large whimsical rear garden pair seamlessly with a full slate of recent upgrades, including new electrical, HVAC, windows, insulation, siding, and lighting, creating a truly turn-key space. Ideally situated just one block from the Jitney, LIRR, Shelter Island Ferry, multiple hotels, and municipal parking, and surrounded by Greenport’s vibrant shops, restaurants, and waterfront.

311 Front Street, Greenport

$2,795,000

7 Beds ⋅ 7 Baths ⋅ 1053367 MLS

Home Complete! Professional Photos Coming Soon. Exceptional new construction by well-known local builder set on .42 acres with approximately 4,600 sq. ft., offering 7 bedrooms and 6½ baths. Sophisticated design features include 10’ ceilings, 4” white oak floors, European windows, Cortizo doors, architectural roof, and Hardie Plank siding. Designer kitchen with Taj Mahal quartzite countertops, waterfall island, custom cabinetry, butler’s pantry, Thermador appliances, XO hood and wine refrigerator. Luxurious first-floor junior en suite and stunning second-floor primary suite with spa-like wet room, soaking tub, walk-in closet and mahogany balcony. Living room with gas fireplace, finished lower level, heated 18’ x 36’ in-ground pool, irrigation and professional landscaping. Detached two-car garage with overhead storage. A new construction offering space, style and sought after amenities. Close to 67 Steps Beach and moments from all that Greenport has to offer.

1050 Tasker Lane, Greenport

$599,999

1057890 MLS

HALF ACRE CLEARED AND FLAT LOT FOR SALE IN THE HEART OF THE VILLAGE! 150 FT X 145 FT is zoned R2. The lot size and 150 feet of road frontage meet the village building standard for a potential SUBDIVISION for two 1/4 acre buildable lots. Building standards also allow for a LARGE SINGLE FAMILY or MULTIFAMILY HOUSE WITH POOL. NO PLANS HAVE BEEN SUBMITTED AT THIS TIME AND ALL PLANS AND SUBDIVISIONS ARE SUBJECT TO BUILDING DEPARTMENT APPROVAL. NEW SURVEY available upon request.

264 6th Avenue, Greenport

$1,200,000

3 Beds ⋅ 2 Baths ⋅ 1053439 MLS

Located in the Stars Beach Community, this charming 3-bedroom, 2-bath cottage offers the perfect opportunity to create your own beach-town escape, weekend retreat, or year-round home. Chill in your backyard, lounge in your pool or enjoy the neighborhood beach and stay to watch the spectacular sunset then rinse off the sand in your outdoor shower. Enjoy cozy evenings by the wood burning fireplace or stay cool with central AC. Includes finished basement with outside access, garage, accessory shed, solar. Moments from North Fork's celebrated farm stands, restaurants, marinas, boating, award-winning wineries, and charming local shops. A true North Fork lifestyle opportunity in a wonderful beach community-come make it yours.

3825 Stars Road, East Marion

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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.