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621 Main Street, Greenport

6 Beds, 4 Baths, 5,590 SqFt
Restored 1880 Church With Bell Tower, Balcony, Large Open Floor Plan With Gourmet Kitchen, 5 Bedrooms, 4 Full Bathrooms, Cac, Gym. Large 10,400 Sf Lot Leaves Plenty Of Private Outside Space - Rare For The Village. Stained Glass, Soaring Ceilings. Architectural Details In Tact!

3225 Main Road, Greenport

7 Beds, 5 Baths,
Style And Charm On 4.9 Acres Of Beautiful Land With Detached 2 Car Garage. Entrance Leads To A Spacious Center Hallway With Grand Staircase. 1st Floor Offers Living Room, Formal Dining Room, Eat In Kitchen, One Bedroom, Library, Sun Room And 2 Full Bath. 2nd Floor Offers Master Bedroom En Suite, Additional 5 Bedrooms And 2 Full Bath. Also A Full Basement And Full Attic.

18 South Street, Greenport

1 Bed, 3 Baths, 3,295 SqFt
Live/work in mint condition fully restored multi-use building in the heart of Greenport Village, close to all village amenities & public transportation to NYC. Offering a unique combination of 1st floor retail space, large gallery/work area & beautifully appointed living quarters with 2nd floor balcony. Street access front & rear, 2 parking spaces. Excellent rent history.

18 South Street, Greenport

1 Bed, 3 Baths, 3,295 SqFt
Rare Live Work opportunity an exceptional historic commercial building in the heart of Greenport Village. Totally renovated mint condition building is move-in ready. Upstairs beautifully renovated 1 BRM apartment with possible expansion of living space. Downstairs suitable for a gallery, showroom, retail or office space. Several configurations possible. Modern conveniences with historic charm; high ceilings, hardwood floors, 2.5 baths,

1015 Sound Drive, Greenport

3 Beds, 3 Baths, 2,300 SqFt
Contemporary & chic, mint condition home in Eastern Shores, Greenport on spacious half acre lot. Renovated with open light-filled floor plan, 18x36 pool, teak hot tub, surrounded by cedar deck with entertaining area. First floor sleeping, custom gourmet kitchen, hardwood Brazilian cherry floors, Indian stone polished kitchen counters & master unpolished floor, second floor master bedroom with bath & balcony, 2nd common space balcony.

152 Central Avenue, Greenport

3 Beds, 3 Baths, 2,342 SqFt
This worldly village gem, circa 1903 has been expertly renovated and restored with style and comfort in mind and has been impeccably maintained. First floor Den/Master suite with fireplace & separate entrance. Two second floor bedrooms one with an en-suite bath. Intimate slate courtyard with pergola invites outdoor entertaining. Accessory out building is ready for your imagination. Located in the heart of downtown Greenport Village. View

314 North Street, Greenport

2 Beds, 1 Bath, 576 SqFt
2 Bedroom, Full bath, Living room/Dining room quick walk to town and school

655 Flint Street, Greenport

4 Beds, 2 Baths, 1,700 SqFt
4 Bdrm, 2 Full Bath Greenport Colonial with Extended Outdoor Garage, Permitted For Scallop or Fish Shop, Large Shed, Two Staircases, Sun Porch and Expansive 420sqft Rear Deck Overlooking Large and Private Fenced In Back Yard. Refinished Hardwood Floors and Updated Kitchen on First Floor. Less Than A Half Mile Away From A Sandy Bay Beach, Park And Dock With Views of Shelter Island And near The Heart of Greenport Village.

21 Stirling Cove, Greenport

2 Beds, 3 Baths, 1,242 SqFt
Recently upgraded townhouse condominium in coveted Stirling Cove, with beautiful Harbor & Bay views and deeded boat slip in protected marina. Complex has heated in-ground pool, private beach & two tennis courts, all located just a short walk to Greenport Village. The 2 bedroom, 2.5 bath unit has wood burning fireplace, newly upgraded kitchen, renovated ground floor powder room, 2 ensuite bedrooms on second floor and full-time on-site

117 Sterling Street, Greenport

3 Beds, 4 Baths, 4,500 SqFt
Opportunity knocks! Classic 4500sf water view home on .68 in Greenport Village. Includes a gentleman's marina, 8-slips on Sterling Harbor w/ 8.5' MLT depth, producing $40K annually.Home & dock reconstructed in 2003.This home was rebuilt w/ the finest materials & modern amenities. Rosewood floors, custom kitchen, CAC, w/ a nod to the past incorporating antique built-ins & ornate fireplaces. Professionally manicured grounds, pergola

103 Sterling Street # B, Greenport

2 Beds, 2 Baths, 790 SqFt
Enjoy easy, breezy living at this turn-key ground floor co-op with stunning harbor front views. This beautifully updated unit features an open water view kitchen and living room with a relaxing waterside deck. Perfect as a pied a Terre or for year round living. Conveniently located near all of Greenport's fabulous dining, shops, and seaside historic charm. Keeping it simple never looked so good.

905 9th Street, Greenport

3 Beds, 3 Baths, 1,500 SqFt
This home has had a total renovation from the studs. Everything is new - the owner is relocating. This North Fork property is just a stone throw from Greenport Village. The home offers excellent vacation rental potential, and is a terrific, convenient summer retreat.

503 1st Street, Greenport

4 Beds, 2 Baths, 2,550 SqFt
Investment opportunity! 2 homes on 2 separate adjacent lots sold as a package, being offered for the first time after decades. 503 1st St offers a spacious two floor house that radiates with 4 cozy bedrooms, 1.5 bathrooms, Eat in Kitchen, Formal Dining room, Cozy Living room, Porch, Den, Parlor and an attached Work Shop and garage. 110 Center Street is a shell that can be restored or removed and offers the opportunity to rebuild creatively.

738 Conklin Road, Greenport

2 Beds, 1 Bath,
This gorgeous newly remodeled home is Ideally located in Greenport's private bay beach community, Peconic Bay Estates. Completely remodeled in 2020, this special home offers a brand new kitchen, stainless steel appliances, custom built in eating area, new floors, new HVAC, new 12x40ft deck with water views, new driveway, garage doors, & fresh sod/landscaping. Wonderful natural lighting throughout pristine home.

317 South Street, Greenport

4 Beds, 2 Baths,
Look No Further! Adorable 4 Bedroom Summer Rental In Historic Greenport Village. Easily Access All The Amenities That Village Life Has To Offer, Restaurants, Shops, Beaches, Wineries, Museums, And More!

42 Stirling Cove, Greenport

2 Beds, 3 Baths,
Beautiful immaculate lower level true waterfront Unit. Tennis heated pool, beach, Green area. Walk to town and all Restaurants



The hamlet of Greenport, which is in the Town of Southold and is also home to the incorporated Village of Greenport, is the most popular and well-known hamlet on the North Fork of Long Island.

Because of its deep and protected harbor, Greenport was a major whaling and ship building port in the 18th and 19th Centuries. By the mid 1800s, the fishing industry employed thousands. The Long Island Railroad arrived in 1844 and was a driving force in the development of Greenport and the North Fork, as local farmers used the railroad to ship their harvest to markets. Greenport became an oyster hub in the early 1900s and, at one time, there were more than a dozen oyster factories.

As the oyster industry began to shrink, Greenport transformed itself once again and became one of the premiere vacation destinations on the eastern seaboard. Historic homes, a nod to Greenport’s rich past, line the streets and avenues of the small village which features many boutiques, shops, restaurants, B & B’s, hotels and even its own micro-brewery. Mitchell Park, overlooking historic Greenport Harbor, features a marina, an antique carousel and public dock space. The park is also home to free concerts and theatrical performances.

Throughout its long history, Greenport has been known by several different names, including Winter Harbor, Stirling, and Green Hill. At a public meeting in 1831, residents officially adopted the name Greenport.

The Village of Greenport is the North Fork’s only incorporated village. It has its own mayor, as well as its own water, sewer and electric. Beyond the borders of the Village there are sound- and bay-front beaches, both public and private, as well as many beautiful homes.

Greenport Kids attend the K-12 school on a campus located on the west end of the village.

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