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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.

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

1790 Grandview Drive, Orient

4 Beds, 4 Baths, 3,900 SqFt
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 Drive, Orient

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

110 Soundview Road, 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

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

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 Street, 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.

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

220 Navy Street, Orient

3 Beds, 1 Bath, 1,166 SqFt
Mid 19th C, 2-story former Bayman's home with 3 bedrooms, & original out-building located in the heart of Orient Village. Beautiful, extra wide .25-acre lot, a short walk to Orient Harbor, Yacht Club, Bay & Sound beaches & all village amenities. This property is located in the Orient Historic District.

420 Willow Terrace, Orient

Orient Village half acre lot with waterviews and deeded sandy bay beach rights with BOH, Building & DEC permits in place. This village location is not in a FEMA flood zone and is shovel ready with approvals in place.

600 Youngs Road, Orient

3 Beds, 2 Baths,
Expanded Ranch Set on Private .46 Acres Near the Historic Village of Orient with its Beautiful Wharf Area, Quaint Shops and Orient Yacht Club. Perfectly Located Between Village Lane and Spectacular LI Sound Beach. Enjoy All that the North Fork and Quiet Coastal Lifestyle Offers.

45 Platt Road, Orient

3 Beds, 2 Baths, 1,722 SqFt
Charming and authentic, historic 18th C home in Orient. Wide floorboards, exposed beams, original built-in cabinets. Just a short distance from beautiful Hallock Bay Beach, Narrow River Marina & all Orient Village amenities. Charming rear deck off dining room & kitchen with mature grape arbor. Excellent rental history.

2420 Plum Island Lane, Orient

3 Beds, 1 Bath, 1,400 SqFt
Bright Open Concept Roomy Ranch in Coveted Community of Orient By They Sea! Perfect Location for Boaters and Water Lovers. Close to Cross Sound Ferry, Orient Beach State Park and Public Marina. Room For Pool & Access To Private Association Beach & Park.

1030 Uhl Lane, Orient

Level 1-acre lot with mature trees in Orient-By-The-Sea, just a short walk to a beautiful association park & sound beach. Close to local marinas and Orient State Park, offering hiking trails & 45,000 ft. of frontage on Gardiner Bay.



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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