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Main Road, Orient

Rural Simplicity. 33 Acres Of Prime Waterfront Property On The Li Sound With Development Rights Intact. 425' Of Private Beach Is The Perfect Backdrop For Both Sunrise And Sunset Views. Coveted And Pristine. This Is Your Canvas To Let Your Vision Unfold.
Status: Active

1207 Birds Eye Road, Orient

5 Beds, 3 Baths, 2,400 SqFt
This home is located in one of Orient's most premier, private and coveted estate enclaves known as "The Hill". Rare Orient mid-century sound front home set on a shy 1.5 acre lot with 225 ft 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 bedroom 3 full bath home with unparalleled views and absolutely stunning sunsets from all rooms.
Status: Active

28410 Main Road, Orient

New to the Market! Be a Gentleman "Farmer" in your very own "Dell!" 34.5-acre farm with a mature apple orchard and multiple farm buildings and paddocks to house horses, and other livestock and vegetation to suit your fancy. There is also a large greenhouse and an approved plan to build an 8,600 square-foot agricultural building. The 34.5 acre farm is protected by deer fencing and consists of 29.5 acres of agricultural land
Status: Active

335 Village Lane, Orient

4 Beds, 3 Baths, 2,750 SqFt
Orient Village perfection offered for Sale! c1850 Beautifully curated, this meticulously restored spacious Orient village beauty is impeccably finished and designed through out. This Orient Village refined residence boasts elegant open living, 1st flr Bedroom w/ Bath ensuite, including 3/4 bedrooms, 2.5 baths, Chefs kitchen, formal dining, great room w/ fireplace, 4 season sun room with long Farm table for 12, exercise room, laundry room. Enjoy
Status: Pending

370 Munn Lane, Orient

3 Beds, 3 Baths, 2,151 SqFt
Stylish and chic Mid-Century Contemporary home on 1 plus acre with heated 15"x75" heated gunite pool offering exceptional privacy and distant bay views. 3 bedrooms, 3 full baths, CAC, sunroom, 2 bay garage, wood burning fireplace and wood stove, solar panels. Included in the sale is the addition abutting .75 acre vacant lot at 950 Maple Lane that has a fractional share of a private sound front beach.
Status: Pending

450 Hillcrest, Orient

5 Beds, 6 Baths, 4,700 SqFt
Exquisite NEW CONSTRUCTION In Orient- Location Location Quaint Picturesque appx.1 acre property Backing 23 acres of Vineyards. Exceptional Attention to Architectural Design and Details- Finest Craftsmanship & Materials Soaring Two level Entry Leads to Expansive Principle Rooms -High Ceilings-Tray & Coffered, White Oak Hardwood floors throughout, Impressive Millwork. Three Master En Suites PLUS two additional bedroom En Suites, Huge
Status: Active

450 Harbor Road, Orient

3 Beds, 2 Baths,
You will not want to leave this Bayfront beauty! Incredible location in coveted Orient Village with 100ft of beachfront, stellar sunrises and sunset views! Overlooking Orient harbor and Shelter Island. Lounge in the pool, or lie on your beach. Newly renovated with a full house backup generator, gourmet kitchen, 3 beds, 2 baths, fireplace, outdoor fire pit and a basement that can accommodate an office, gym and storage. Next to a preserved bird
Status: Active

1425 Orchard Street, Orient

4 Beds, 3 Baths, 2,300 SqFt
Orient Village C1800's designer's expertly renovated 4 bedrooms, 1 full & 1 plus half baths, set on 1.1 acres w/ large 2 story c1800's barn w/high ceilings restored into parking/work studio & art studio w/large deck, & outdoor Shower. This tastefully designed residence features large bright living room with impressive oversized wood burning fireplace, stunning chef's kitchen, dining area with large doors opening to lush 1.1 acre
Status: Pending

110 Soundview Road, Orient

5 Beds, 9 Baths,
New Construction Unique Contemporary over 4800 Sq. Ft. Home in Orient By the Sea. Hop, Skip and Jump to the Beach. Invite Your Extended Family and Friends to Enjoy the Dramatic Sound Views from Many Rooms While Maintaining Your Own Privacy. A True Country Club Lifestyle and an Entertainers Delight. Featuring Gourmet Kitchen with Gas Fireplaces, 5 Ensuite Bedrooms, a Panoramic Rooftop, Private Trex Porches, Multiple Garden Areas, Beautifully
Status: Pending

3480 Orchard Street, Orient

2 Beds, 3 Baths, 1,408 SqFt
Mid-Century style Ranch on 1.3 pastoral acre lot on Orchard Street in Orient. Land is cleared with gardens and many specimen trees. Open concept living room/dining room with wood burning stove, 2 bedrooms, 2 updated full baths and updated eat-in kitchen. There is a separate 2-car garage with 2nd floor workshop and half bath. Plenty of room for pool or accessory structures. Close to all beaches, marinas, and Orient Village amenities.
Status: Active

1000 Soundview Road, Orient

3 Beds, 4 Baths, 1,850 SqFt
Stunning 2020 newly renovated custom finished home built with precision and meticulous high quality finishings includes an inground swimming pool & private beach area with sound access steps away. This exquisite cedar shingled home boasts an open concept floor plan exuding natural light throughout including hi ceilings with exposed wood beams & solid wide planked oak flooring. The brand new kitchen includes an elongated quartz
Status: Pending

325 N Sea Drive, Orient

4 Beds, 4 Baths, 2,800 SqFt
Beautiful Home On Scenic Half Acre In Desirable Neighborhood of Orient By The Sea! Open Floor Plan, LR W/ Large Stone Fireplace, High-End Kitchen w/SS Pkg & Granite. 4 Bedroom, 3.5 Bath Home w/Master on First Floor. Large 2nd Floor Bonus Room!. Pool Permit In-Place. Community Private Beach For Residents. Perfect Year Round or Second Home!
Status: Pending

585 Orchard Street, Orient

4 Beds, 2 Baths,
Quintessential 19th Century Orient Farmhouse located on the coveted Orchard Street in the heart of Orient Village. Classic Front Porch, hardwood floors throughout, marble bathroom. Walking distance to Orient Yacht Club, village amenities, marina, bay beaches.
Status: Pending

1750 Orchard Street, Orient

1.41-acre lot on Orchard St in Orient Village. Included with the purchase are plans for a 4-bedroom, 3.5 bath innovative, custom built, contemporary home of approximately 3,700 sq ft, with pool and pool house. All structures are designed and sited within the established specimen trees and natural landscape. A test well is in place with Heath Department permit pending.
Status: Pending

285 Oyster Ponds Lane, Orient

2 Beds, 1 Bath, 900 SqFt
Just a couple of doors down from The Candy Man shop is this 2 bedroom, 1 bath cottage in historic Orient. Sitting on .30 acres on beautiful Oyster Ponds Lane and only moments from Village Lane restaurants and shops, Poquatuck Park and Orient Yacht Club, one can create their dream home in this peaceful neighborhood.
Status: Pending

435 Narrow River Road, Orient

3 Beds, 1 Bath, 1,020 SqFt
Enjoy unobstructed protected panoramic views of Gardiners Bay and Long Beach, across from preserved land. Close to beautiful beach and a short stroll to all village amenities. House and Property being sold as is.
Status: Pending



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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