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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.

38099 Main Rd, 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

1790 Grandview Dr, Orient

4 Beds, 4 Baths,
Stately, Solid, Approx. 3,900 square foot Sound Front home featuring Generous First Floor Master Suite, Updated Kitchen, Family Room, Den with Fireplace, Office and a Formal Dining Room. Large Waterside Yard with Patio and Room for Pool with Proper Permits. Roof is 3 Years Young. Stairs in Place to Your Own Beach. Located in Desirable Grandview Estates.

2830 Grandview Dr, Orient

5 Beds, 4 Baths, 3,550 SqFt
Updated contemporary split level 5/6 bedrooms home with sweeping views of the Long Island Sound and private stair to an amazing beach. Mature landscaping with a large in ground pool, outdoor shower and great entertaining space. Extremely quite and private setting, additional 1 acre adjacent (non water front) lot available and sold separately. Vaulted ceiling in open concept living room and dinning room, separate family room with pocket doors and

4065 Orchard St, Orient

4 Beds, 3 Baths, 3,144 SqFt
Exquisitely designed custom built home on 5 secluded acres in the heart of Orient. Property is landscaped with mature spruce & cedar trees, Russian olive groves & flowering beds. House has dramatic open common spaces and first floor master suite that open onto wrap around decks, pergola walkway & screened porches. New gourmet kitchen, updated baths, screened porches, expansive awning covered deck, large separate garage (access on two

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

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, 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.

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 additional bedroom with New lux Bath, a fireplace, & CAC. New in-Ground Unite pool, pool house and outdoor shower. New cedar Fence

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

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.

1115 Southview Dr., Orient

3 Beds, 2 Baths, 1,768 SqFt
Authentic & charming 18th C home, c 1720. One of the first to be moved (by barge from Southold) to coveted Brown's Hill Association. Beautifully restored & maintained with original wide board floors, original exposed beams, 2 fireplaces, updated kitchen & baths, CAC, professional outdoor wood pizza oven, beautiful private back yard. ... & so much more. Deeded association Sound beach a short walk from the house.

845 Orchard St, Orient

4 Beds, 2 Baths,
Price Reduced! Now $799,000. 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!

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.

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 2 bay barn w/1st floor storage, workshop, 2nd floor storage. Room for pool.

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



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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