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Main Rd, 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.

22540 Main St, 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.

22540 Main Rd St, Orient

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.

110 Soundview Rd, Orient

5 Beds, 8 Baths, 4,800 SqFt
Contemporary gated home in Orient-By-The-Sea in mint condition. New construction with 4800 sq. ft. of gracious entertaining/living space & dramatic Sound views from many rooms. Featuring gourmet kitchen with gas fireplace, 5 en-suite bedrooms, private porches. Outdoor space has large in-ground pool with outdoor cabana/bar. 3-car detached garage, terraced plantings surround the house & outdoor patios. Short walk to association Sound front

2395 King St, Orient

5 Beds, 4 Baths, 4,338 SqFt
Exquisitely restored and renovated 19th C home, located on coveted King St. in Orient Village with open field views. Main house has gourmet kitchen, 2 fireplaces, original hardwood floors, sunroom, CAC, upper balcony. Restored year-round guest house has 2 bedrooms & large common space, fully heated with AC. Gunite heated swimming pool, sep. garage/studio, large deck with pergola, outdoor shower, potting station & so much more. SQ Ft Main

1110 Orchard St, Orient

3 Beds, 2 Baths, 1,792 SqFt
Quintessential 19th C Orient Farmhouse located on coveted Orchard Street, in the heart of Orient Village. Main house has three bedrooms, two full baths, two fireplaces, formal dining room and garden room. Private rear garden has Gunite pool, separate pool house/studio with half bath and outdoor shower. Walking distance to all village amenities, marina, bay and sound beaches.

2720 King St, Orient

3 Beds, 2 Baths,
Located in a quiet seaside part of Orient Village; This newly renovated cedar shingled home overlooks acres of estuary and salt marshes and is only steps to the beach. Its open floor plan includes a New Chefs kitchen, dining and living area with fireplace. First floor master bedroom with new Lux bath en suite and 2 additional bedrooms with New lux Bath, a fireplace, & CAC. New in-Ground Unite pool, pool house and outdoor shower. New cedar

715 Willow Terrace Ln, Orient

3 Beds, 3 Baths, 2,100 SqFt
This Post-Modern Home is spacious and bright with 3 bedrooms and 3 baths on Willow Terrace in Orient Village. Just a short walk to private deeded bay front beach. Offering wood burning fireplace, bay views from second floor, large sun room, outdoor shower and carport. This .56-acre lot offers unique privacy and room for a pool.

560 Grandview Dr, Orient

4 Beds, 3 Baths, 2,856 SqFt
Winter waterviews and a short distance to Orient Village in a quiet seaside Estate enclave, this thoughtfully built home offers relaxed living space w/open kitchen, dining and living area w/large wood burning fireplace and is perfect for entertaining. There are 4 bedrooms and 3 baths. The master bedroom with fireplace and en suite bath w/sep shower & spa tub. Sep laundry room, Large basement and 2 c/garage with high ceilings. All set upon a

845 Orchard St, Orient

4 Beds, 2 Baths,
Price Reduced! Now $899,000. Solid Cape with Large Rooms on Large Lot in Great Orient Village Location Awaits Your Personal Touch! Four Bedrooms! 2 Car Garage plus Additional Out Building with Electric. Room for Pool!

26700 Main Rd, Orient

4 Beds, 3 Baths, 2,430 SqFt
19th C Farmhouse on .75 acre. Stunning views of open farmland. 4 fireplaces, country kitchen, dining room, front parlor, library, brick patio w/grape arbor. 2nd floor master w/bath & fireplace. Original architectural details. 38 windows provide sunny exposures. Detached 1-car garage. 550 sq ft barn with 2 bay garage, workshop, 2nd floor storage. Room for pool.

435 Narrow River Rd, 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.

39405 Main Rd, Orient

3 Beds, 2 Baths, 2,000 SqFt
Beautifully Restored 3-Bed, 2-Bath Farmhouse On .83 Acres. Inviting Entry With A Light & Bright Living Room To The Left And A Spacious Formal Dining To The Right. Through The Dining Room Is The Gourmet Eat-In-Kitchen And Den W/ Wood-Burning Fireplace Which Leads To A New Wrap Around Trek Deck. Wood Floors Throughout, Cac, Gas Heat, And Large Attic With Potential For Studio Space. Add'l 2 Story Garage With Studio Above. The Grounds Allow

650 Three Waters Ln, Orient

3 Beds, 4 Baths, 2,300 SqFt
Orient By The Sea Contemporary Home- Features An Open Floor Plan With Soaring Ceilings, 2 Story Stone Fireplace, 3 Bedrooms/3.5 Baths - Master On Each Floor Plus 2 Car Garage With Loft. Relax By The Pool Or Soak In The Hot Tub. All This Down The Road From Your Private Sound Beach And Around The Corner Orient State Park And Cross Island Ferry.

39695 Main Rd, Orient

3 Beds, 2 Baths, 1,500 SqFt
Stylish Orient Ranch w/ Legal Apartment Above 2 Car Garage! Main Residence Features Hardwood Floors Throughout w/ Custom Built Cabinets In Both Bedrooms, Kitchen & Living Area. Legal Apartment Offers 1 Bedroom, 1 Bath, Living Area & Kitchen. The Grounds Are Expansive w/ Views Of Orient State Park, Room For Pool or Tennis Court & Could Accommodate Horses Or Perhaps A Recreational Farm. Beach Rights To Truman Beach & Narrow River

23530 Main Rd, Orient

3 Beds, 2 Baths, 1,370 SqFt
Classic Arts & Crafts bungalow style home in Orient. Three bedrooms, updated kitchen and baths, new appliances throughout. Finished accessory outbuilding, currently used by the owner for "home occupation". Beautifully maintained with large rear yard that has room for a pool. Short walk to Orient Village, Country Store, Post Office beaches and marinas.



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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