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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.

825 Stephensons Road, Orient

9 Beds, 7 Baths, 5,800 SqFt
Rare Opportunity! Extraordinary Water views and Sunsets Orient Sound Front Estate C1860's Main and guest home situated on 5 sound front acres, restored with modern day luxuries using superb craftsmanship, the finest materials, lux and designer finishes, fixtures and appliances, and extraordinary details throughout; The Cedars is an Iconic 19th century Victorian with a rich history and placement in Orient and its seaside landscape. The main and

38099 Main Road, Orient

3 Beds, 2 Baths, 2,000 SqFt
This spectacular home located on .67 acres with over 100+ feet of sprawling private beach on the LI Sound. This unique and chic property is a rare gem on the North Fork. Newly renovated, this 2000+/-SF home has 3 bedrooms, including 2 first floor suites, 2 baths, a gas fireplace, high ceilings, custom panelled walls and a magnificent sunroom opening up to amazing views. The property also features a one car garage, Gunite Lap Pool with electric

22350 & 22420 Main Rd, Orient

Two single and separate business zoned properties located at the intersection of Main Rd and Village Lane, Orient. 22350 Main Rd is location of a third-generation family owned candy/ food production/ retail store (2,255 sq ft). 22420 Main Rd is a separate business office, potential retail space (296 sq ft). Both properties have ample parking and are walking distance to the village of Orient with excellent Main Rd exposure. Potential for outdoor

1055 Old Farm Road, Orient

4 Beds, 5 Baths, 4,000 SqFt
Exquisitely designed and custom built Orient Village 3,800+/- sf, 4-bedroom, 6-bath Modern Farmhouse, new construction and gunite pool, on a quiet Village 1.5 acre lot. Rarely will you find a 1.5+/- acre property in Orient Village only with the superb attention to design and detail that a well deserved buyer expects in a move-in-ready home. The home thoughtfully has 3 master bedroom suites, two on the first floor and one on the second floor,

25500 Main Road, Orient

7 Beds, 10 Baths, 3,358 SqFt
The Orient Inn, operating as a successful 5-star B&B, is a restored Arts & Crafts residence backing onto 74-acres of farmland. This majestic home has original details, original wood trim, modern chef's kitchen, 2 gas fireplaces, new mechanicals, new cedar siding, 7 bedrooms, 7 full baths, 3 half baths, 3rd floor attic bonus space & accessory building. 1st floor master bedroom with full bath, private rear entry with deck & private

110 Soundview Road, Orient

5 Beds, 9 Baths,
New Construction Unique Contemporary over 4800 Sq. Ft. Gated 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,

1600 Soundview Road, Orient

3 Beds, 3 Baths,
Beautifully appointed Victorian in desired Orient By the Sea Private Beach Association. Stunning LI Sound views, private beach literally steps away, across the street! Formal DR w/ water views, eat-in-kitchen, SS appliances, granite countertops, open to formal LR w/ gas, stone fireplace. The LR is open to a sitting area overlooking front porch w/ beautiful water views! Master ensuite w/ turret, overlooking Sound, bath w/ jac. tub & shower.

650 Soundview Road, Orient

3 Beds, 4 Baths, 2,500 SqFt
Located within a coveted private Sound front neighborhood in Orient, you will find this extraordinary water view home. This unique property is perfectly situated to take advantage of its beautiful Sound front views overlooking a sea side parcel across the road. The modern Craftsman features 2600 sqft of open living space, 3 beds, 3.5 baths, chef's kitchen, oversized great room with magnificent Rumford wood burning fireplace, master suite with

22540 Main Road, Orient

Prime Business or Residential zoned property, gateway to Orient Village, located at the corner of Village Ln. and Main Rd. Classic 19th C building with wrap around porch, open floor plan with potential for a variety of business uses and/ or habitable second floor. Established parking lot and large corner yard/ garden enclosed by privet hedge.

22540 Main Road, Orient

2 Beds, 2 Baths, 2,500 SqFt
Prime Business or Residential zoned property, gateway to Orient Village, located at the corner of Village Ln. and Main Rd. Classic 19th C building with wrap around porch, open floor plan with potential for a variety of business uses and/ or habitable second floor. Established parking lot and large corner yard/ garden enclosed by privet hedge.

730 Bight Road, Orient

4 Beds, 3 Baths, 2,300 SqFt
Sound view home in Petty's Bight at Orient. Private & serene mint condition, 4 bedrooms, 3 baths. 20'x40' pool on shy 1-acre lot. Private walk-out sound beach just a short walk from the house. Sunny and bright, with CAC, two sound view decks, ground floor bedroom, security system, attached 2-car garage & separate detached 1.5-car accessory garage with 2nd floor storage. Parklike setting, beautifully landscaped including a 30'x50' koi

1405 Village Lane, Orient

3 Beds, 2 Baths,
Beautifully preserved 19th C Home in the heart of Orient Village. Enjoy entertaining on the large screened 3-season porch that opens onto a picturesque rear garden. Recently updated sunny home, new CAC, gourmet stove, custom cabinetry, formal dining room, and original radiators. Walk to post office, Country Store, yacht club, marine, bay and sound beaches. Home is in the Orient Historical District.

155 Three Waters Lane, Orient

3 Beds, 4 Baths, 2,400 SqFt
Classic Orient Charmer. This Stylish Cape Home Features 3 Ensuite Bedrooms, Main Level Master, Two Fireplaces, Walk-In Pantry, Large Eat-In Gourmet Kitchen, Wide Plank Wood Floors, High Ceilings, Wired For Sound, Out-Door Shower, Room For Pool, Steps To Amazing Association Beach.

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.

39595 Main Road, Orient

4 Beds, 3 Baths, 2,400 SqFt
In the heart of Orient's country setting rests this traditional 4 bed 2.5 bath home.Enter property via horseshoe d-way leading to large front porch which flows into inviting foyer, FDR, den & open EIK/LR combo. Large deck off rear of the house enjoys privacy of meticulously landscaped yard compliments of established 10' privet.Second level features 3 guest bedrooms, 1 FB & Master En-suite with additional private bath.Commercial Marina



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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