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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.

1 Mulford Ct, Orient

4 Beds, 4 Baths, 3,698 SqFt
Stunning Contemporary Home Beautifully Set On 5.8 Artistically Landscaped Acres Near Orient Pt. Spacious, Light Filled Rooms With Panoramic Views From Most Rooms. Chic Design, Wrap Around Deck On 1st Floor, Gourmet Kitchen, 2 Fireplaces. Upper Balcony Off Master Suite. 20'X40' Vinyl Pool Overlooking Bluff. Clay Tennis Court. 179.4' Frontage On Sound Beach.

196 Willow Terrace Ln, Orient

3 Beds, 2 Baths, 1,704 SqFt
One Of A Kind Jewel On Orient Bay Offers Unparalleled Views Of Its Sailboat Races & Magnificent Sunsets. Loft Master W/Bath & Walkway Over Cathedral Ceiling In The Living Room To An Upper Deck. (Upper & Lower Decks, Ipe Wood.) Additional 2 Bedrooms W/Bath & Outdoor Playhouse Add To The Allure Of This Unique Home. Private Dock W/Running Water Will Accommodate A 22-Foot Boat. Cac, Lawn Sprinkler System, Pea Stone Gravel Driveway

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. Electric Fence Installed By Fido's Fences.

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.

320 North View Dr, Orient

4 Beds, 2 Baths, 1,800 SqFt
A Once In A Lifetime Opportunity To Restore This Enchanted Mid Century Modern In The Exclusive Waterfront Enclave Of Brown's Hills. Sweeping Waterviews Of The Long Island Sound Span The Entire Home; With Sound Facing Deck Along The Entire Northern Exposure. Rare Chance To Put Your Vision And Imagination To Work On This Waterfront Diamond In The Rough. Association Dues Upon Request.

455 Three Waters Ln, Orient

3 Beds, 3 Baths, 2,100 SqFt
Bright, Mint Condition Contemporary Home In Orient-By-The-Sea. 10' X 36' Saltwater Gunite Lap Pool. A Short Stroll To Association Sound Beach. Open Floor Plan W/Fireplace, 3 Bedrooms, 2.5 Baths, 2-Car Garage. Loaded With Luxurious Amenities: Radiant Floor Heat, Wolf & Sub-Zero Appliances, Franke Kitchen Sinks, Multi-Zone Irrigation, Front Loading Washer/Dryer & More.

1000 Soundview Rd, Orient

3 Beds, 4 Baths, 1,900 SqFt
3 Master Bedrooms With 3 Master Baths Ensuite, Open Floor Plan, Chefs Kitchen, Dining Room, Great Room With Fireplace, Separate Den, Guest Half Bath, Full Basement, Cac, Lovely Grounds With Patio And In-Ground Pool Only Steps To Private Association Beachfront In Great Orient Location.

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.

280 Greenway East, Orient

3 Beds, 2 Baths, 1,944 SqFt
Orient, Green Acres. Drive East And Head For For Your Own Piece Of Orient. Built In 2000, This Spacious And Light Cape Is Set On A Landscaped Half Acre Just Around The Corner From Your Deeded Sound Beach. 3 Br, 2 Ba Include A Master Suite On The 1st Floor. Expansion Potential In Unfinished 2nd Floor Space. Open Floor Plan, Wood Stove. Lovely Covered Rear Porch With New Cedar Decking Catches The Morning Sun. Near Orient State Park And Cross

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.



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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