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38255 Main Road, Orient

Located in coveted Orient point, this 33 acre parcel has 425' of private Sound front beach, breathtaking sunsets and incredible sunrises. Full development rights, so you can create your family compound or a lifestyle subdivision! Let your imagination roam free! Close to Greenport and all the North Fork has to offer, bountiful farm stands, renowned restaurants, beaches, marinas, boating, award winning wineries and great shopping.
Status: Active

N/A, Orient

Breathtaking Views From This 11 Acre Waterfront Parcel. With Approximately 500 Feet On The Long Island Sound. A Low Bluff Allows You To Step Out And Stroll Down To The Water. Watch The Magnificent Sound Sunsets. A Quiet And Peaceful Spot To Build Your Dream Home. In Close Proximity To The Cross Sound Ferry From Connecticut. A Short Drive To The Best Farm stands And Vineyards On The Island As Well As Delicious And Award Winning Restaurants.
Status: Active

1790 Grandview Drive, Orient

4 Beds, 4 Baths, 3,900 SqFt
Welcome to 1790 Grandview Drive! This stately Sound Front Home (approx. 3,900 sf) features a welcoming foyer with soaring ceilings and front staircase, luxurious first floor primary suite w/new hardwood floors, kitchen w/ granite countertops and stainless steel appliances and second stair case, living room and den each having a fireplace, office, half bath and a formal dining room. Upstairs has an extraordinarily large landing leading to 3
Status: Active

1010 Bight Road, Orient

5 Beds, 5 Baths, 4,935 SqFt
FRAMING STARTED IN ORIENT! PRICE REDUCTION. Luxurious new build set in Pettys Bight Estates in Orient can be your dream come true. Secluded and private with beach access, this North Fork Nantucket-styled home will offer everything you could imagine with top-of-the-line finishes throughout. What better opportunity to own a brand-new construction with a luxurious feel and the opportunity to work with the builders to create your forever home on the
Status: Pending

1600 Hillcrest Drive, Orient

6 Beds, 7 Baths, 5,000 SqFt
This elegant new construction home sits high up in Hillcrest Estates in highly desirable Orient just minutes to the cross sound ferry, orient state park, local vineyards, farmstands, and beaches, and a short drive to downtown Greenport. Upon entrance, you are warmly greeted by hardwood floors, 10' ceilings, a bright open floor plan connects the kitchen to the living room with a gas fireplace, one of 3 in the home, and a breakfast room with views
Status: Active

80 Ryder Farm Lane, Orient

3 Beds, 5 Baths, 4,777 SqFt
Deceivingly Substantive, Stylish New Construction. Drawn, refined and executed with detailed plans by designer & custom build team. Elevate beach neighborhood living with texture as the primary design element. Sophisticated finishes incorporated into a work from home flexible floor plan that is sought after and not often found. Professional, expansive kitchen with custom crafted cabinetry in a color aesthetic specific to this property.
Status: Pending

1207 Birds Eye Road, Orient

5 Beds, 3 Baths, 2,400 SqFt
This home is located at 1207 Birds Eye Road, Orient, one of Orient's most premier, private and coveted estate enclaves known as "The Hill". Rare mid-century sound front home set on a shy 1.5 acre lot with 225 feet of private beachfront sits along miles of Long Island Sound with incredible water views, a seaside deck, and huge seaside screened porch. Offering 4/5 bedrooms, 3 full bath home with unparalleled views and absolutely stunning
Status: Active

150 Hillcrest Drive, Orient

5 Beds, 5 Baths,
Welcome to 150 Hillcrest Dr N. Opportunity knocks as purchasers have the ability to build to suit. The developer of this property are offering design plans ranging from 3500-5000 livable sqft w/ attached two car garage, chef's kitchen, open floor plan, multiple en-suite bedrooms, in-ground pool (w/options) and multiple balconies. The properties unique contour allows for sweeping country views and possible distant bay views as the property sits
Status: Active

28410 Main Road, Orient

Rare opportunity to live your best life on the ultimate North Fork Farmstead surrounded by NYS Preserved land with water proximity in every direction. 5 acre Parcel with Development Rights Intact to design the Country House of your dreams. Plus 29.5 acre working farmstead. This exceptional farm includes many acres of vegetables, an apple orchard, sunflower field, goats, sheep, chickens, horses and other animals as well as multiple farm
Status: Active

960 Willow Terrace Lane, Orient

4 Beds, 4 Baths, 2,700 SqFt
Introducing 960 Willow Terrace. An incredibly rare opportunity to own in coveted Willow Terrace Farms in Orient Village. This property features 130' of water front on Gardeners bay w/ unobstructed views of Shelter Island, Bug Light, Greenport Village, stunning sunsets and panoramic Bay views w/ a private association beach in very close proximity. The home's layout is open featuring a sun soaked great room over looking the Bay with formal dining
Status: Active

2205 Grandview Drive, Orient

5 Beds, 5 Baths, 4,785 SqFt
20x40 Pool & Patio Now Included. Stunning Orient New Construction In Grandview Estates w/ Private Beach Access. Enter through an impressive foyer w/ high sun soaked ceilings, and transition into a stunning great room w/ floor to ceiling glass, chef's kitchen and double sided fireplace. Addt'l main level features are formal dining room with butlers pantry connecting to kitchen, 1st floor en-suite bedroom and formal living room with fireplace.
Status: Active

22350 & 22420 Main Road, Orient

Orient Village, North Fork - NOT TO BE MISSED - two commercial properties each w/a building w/parking, side by side for a total of .42 acres (.21 each) ...Iconic location on Main Road just off of Village Lane. Zoned BUSINESS, which allows for a variety of uses including All uses in A/C zone (tasting room), retail, wholesale, warehouse, BAKING and FOOD PROCESSING, garden/nursery center, beverage distribution, residential 1& 2 family house,
Status: Active

735 Major Pond Road, Orient

4 Beds, 2 Baths, 2,800 SqFt
Private and incredibly peaceful, beautiful bay front community located in the sought after Orient Village. 735 Major Pond Road is set on 1.9 bucolic acres with mature specimen trees and only 200 steps to a 3 acre secluded deeded beach overlooking Orient Harbor. This Cape Cod home features 4 beds, 2 baths plus a 16x24 three season sun-room perfect for relaxing.
Status: Pending

335 Sound View Road Road, Orient

2 Beds, 2 Baths,
This traditional ranch-style home presents a gracious panorama of water and sky with views across the Sound to Connecticut. Nestled among some of the North Fork's finest real estate with forever sunsets is this lovingly cared for home with possibilities galore. Easy one floor living with two beds, two baths, a separate den, a living room and a main porch with wall to wall windows facing the sound opening onto a private stone patio and
Status: Pending

28775 Main Road, Orient

4 Beds, 3 Baths, 2,800 SqFt
Meticulously restored & maintained, the Young's family farmhouse is set on 1.6 acres in Orient, surrounded by preserved open space & farm views. Built in 1869, the house underwent a 1909 renovation, when it was " modernized" to the Greek revival style, expanding the porch, adding a wood burning fireplace, elegant staircase & curved wall enclosing the formal dining room. Original features include second staircase, walk-in
Status: Pending

885 Old Farm Road, Orient

3 Beds, 2 Baths,
Secluded North Fork Cape Situated On 1.27 Acres Featuring 3 Nice Size Bedrooms W/ One On The Main Level, 2 Full Bathrooms, Living / Dinning Room, Eat In Kitchen With Exiting Out To Deck to Back Yard, Unfinished Basement And A 1 Car Garage.
Status: Active



Orient is known as the “Gateway to New England,” because of its local ferry service to Connecticut. In fact, Ferry Service has connected Orient Point to southern New England for more than a century.

Orient is separated from the rest of Southold Town by the “Causeway,” which features some of the world’s most stunning views. Long Island Sound is visible to the north and the serene Gardiner’s and Peconic Bays to the south.

Along with nearby East Marion, Orient was once known as Oysterponds, because of the abundance of shellfish. In 1836 Oysterponds split, forming what is now known as East Marion and Orient. The name Orient was chosen to reflect its easternmost position on the North Fork.

The hamlet was originally settled by five families through a land grant from the King of England in the 17th century. Orient would later be used as a base of operations by British commanders such as Benedict Arnold during the American Revolution conducting raids on Yankee-held Connecticut. Among Benedict Arnold's headquarters was a local tavern owned and operated by the Vail family on what "Village Lane". Many of the hamlet's older structures are included in the Orient Historic District, which was added to the National Register of Historic Places in 1976.

Orient's winter population swells to well over 1000 during the summer months, with many calling Orient their second home. Besides a post office, a gas station, and a country store, Orient has no real business center and depends largely on nearby Greenport for every-day necessities.

Orient Point is home to the area’s largest beach, Orient State Park, featuring one of the most pristine maritime forests on the North Fork. It is a true nature lover’s paradise.

Students attend Oysterponds Elementary School, in Orient, until sixth grade. They then attend Greenport for the remainder of their school career.

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