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Private Rd, Orient

6 Beds, 5 Baths, 5,700 SqFt
Timeless, Sophisticated & Chic. 26 Spectacular Acres W/ 500' Feet Of Private Beach. Understated Elegance Hallmarks The Main House W/ 6 Brs Incl 2 Master Suites, 4.5 Ba & 3 Fpl. Property Features 2 Br Guest Cottage, Pool W/ Pool House, Tennis Court & 3 Car Gar. Unbeatable Setting, Spectacular Sunsets & Absolute Privacy.

Main Rd, Orient

Step Back In Time - Orient In Its Rural Simplicity. 33 Acres Of Prime Waterfront On Li Sound W/ Development Rights In-Tact Is Among The Last Vestiges Of A Lifestyle Rapidly Disappearing. 425' Of Private Beach Is The Perfect Backdrop For Both Sunrise & Sunset Views. Coveted & Pristine, This Is The Place To Let Your Vision Unfold. Less Than 1 Mile To The Cross Sound Ferry.

2440 Village Ln, Orient

3 Beds, 2 Baths, 1,344 SqFt
Historic Bayfront Victorian With 183 Ft. Of Sandy Beach & Large 200 Ft. Dock, In The Heart Of The Village. Charming & Original With Wood Burning Fireplace In The Living Room, Formal Dining Room, Eat-In Kitchen, 3 Bedrooms, 2 Full Baths. Water Side Porch And 1.5 Car Garage. Views Of Orient Harbor From Nearly Every Room. Bayfront Accessory Building. A Unique Property.

300 Latham Ln, Orient

4 Beds, 4 Baths, 3,800 SqFt
Stunning Sweeping Views Of Long Island Sound To Connecticut Including The Coffee Pot Light House Off Orient Point. This Home Adjoins Preserved Property Which Offers Forever Water-Views, Nature Trails And Beautiful Beachfront. This Shingled Style Home Was Built In 2002 Offering A Spacious Yard With In-Ground Pool, Patio And Cabana. Great Home For Entertaining.

420 Willow Terrace Ln, Orient

4 Beds, 5 Baths, 3,000 SqFt
Orient Village- New 3000 Sq Ft Water View Home To Be Built With Use Of Associations Deeded 3 Acre Private Deeded Beachfront Lot . 4 Bedrooms, 4.5 Baths, Fireplace, Kitchen, Seaside Waterfront 1st And 2nd Floor Water View Decks, 2.5 Car Garage, Full Basement. Beautiful Finishes Throughout. In Ground Gunite Pool.

25825 Main Rd, Orient

3 Beds, 2 Baths, 1,626 SqFt
Mint Condition 1830'S Farmhouse With Separate 2-Story Art Studio/Workshop With 2-Half Baths, Gas Heat & Ac. 20X40 Ft. In-Ground Heated Pool, 1 Gas Fireplace, 2 Wood Burning Fireplaces, Gas Hot Air Heat, Cac, Beautiful Original Woodwork & Hardware. Full House Generator.

675 Orchard St, Orient

4 Beds, 2 Baths, 1,786 SqFt
Beautifully Preserved 19th C Orient Village Historic House In The Heart Of Village On Coveted Orchard St. Set On Deep Lot Offering Unique Privacy & Room For A Pool. 4 Bedrooms & 2 Full Baths, Formal Dining Room, Front Porch & Rear Screened-In Porch, Updated Kitchen & Dining Patio Overlooking Large Pastoral Backyard. Close To Bay And Sound Beaches & Village Amenities.

35800 Main Rd, Orient

After 300 Years Of Family Ownership, 1 Of A Few Remaining Large Parcels In Orient For Sale. 23+ Acre Property W/Endless Potential. Adjacent To Main Rd Is A 4.7 Acre Building Site, Overlooks 8.5 Acres Of Farm Land, Currently Under Cultivation. 10 Acre Wetlands Parcel At The Southern Tip Borders Little Bay & Peconic River W/Views Of Orient State Park.

800 Village Ln, Orient

3 Beds, 1 Bath, 1,272 SqFt
Rare Village Lane Charmer. Early 19th Century Farmhouse With Two Story Barn. Potential For Artist Studio Or Use Your Imagination. Orient Yacht Club Is At The End Of The Road.

800 Village Ln, Orient

3 Beds, 1 Bath, 1,272 SqFt
19th C Classic Cape Cod On Village Ln In Orient With Large 2-Story Accessory Barn, Perfect For Artist's Studio/Workshop. Hand-Hewn Beams, Wide Floor Boards, Original Mantles & Privy Are Just A Few Of The Original In-Tact Historic Details Of This Property. Front Porch, Mud Room & Rear Deck Add To The Overall Charm Of The Property. Close To All Orient Village Amenities.

24065 Main Rd, Orient

3 Beds, 2 Baths, 1,500 SqFt
Adorable & Authentic Arts And Crafts Orient Farmhouse. Broad Porch W/Room For Swing, Large Living Room, Opens To Dinning And Eat In Kitchen W/Pantry Beyond. Den W/1/2 Bath Plus 3 Bedrooms And Full Bath Up. 2 Car Garage Building And Spacious, Level Partially Fenced Lawn. Moments To Village Lane And Greenport Amenities. New Roof And Freshly Painted Exterior.

300 Hillcrest Dr, Orient

Build Your Dream Home On Shy One Acre Lot With Vineyard Views And Plenty Of Room For A Pool. Near Historic Orient Village, Shopping, Farms, Wineries, Beaches And Ferry To Connecticut, Sail In Orient Harbor & Gardiner's Bay. Explore Lovely Wetlands In Your Kayak. Catch Stripers And Blues In Plum Gut.

2785 Grandview Dr, Orient

Level, Wooded 1+ Acre Lot. Build Your Dream Home In This Highly Desirable Beach Community In Orient. Property Being Offered With Or Without Mls 2934610. Private Sound Beach Access For Grandview Estates Community.

1600 Hillcrest Dr, Orient

Beautiful Corner Shy 1-Acre Lot At Top Of Hillcrest Dr. In Hillcrest Estates, Orient. Nicely Elevated With Specimen Trees And Native Shrubs. Conveniently Located In Peaceful Enclave Between Orient Village & Orient State Park & 10 Minutes To Greenport Village. Close To Public Sound & Bay Beaches And Marinas. Video Coming Soon.

1240 Latham Ln, Orient

5 Beds, 4 Baths,

32625 Main Rd, Orient

4 Beds, 3 Baths,
Enter Property Thru Tree Lined Drive Which Opens To Expansive Open Fields And Sound Front House! House Sits In The Middle Of 10 Landscaped Acres. House Is Open Floor Plan Of 4,000 Square Feet, Perfect To Enjoy And Entertain. Rear Deck Overlooks 500 Feet Of Private Sound Front Beach With Views To Connecticut.



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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