All Listings Under $100,000 $200,000 - $300,000
$300,000 - $400,000 $400,000 - $500,000 $500,000 - $600,000
$600,000 - $700,000 $700,000 - $800,000 $900,000 - $1,000,000
Over $1,000,000
Refine your search to less than 500 properties to save.
Click on the map to draw your polygon search.
Click on the map to draw your radius search.
Search only mappable listings within the map's bounds.

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.

2830 & 2785 Grandview Dr, Orient

6 Beds, 4 Baths, 3,762 SqFt
Contemporary & Chic 3,762 Sq. Ft. Get-Away On 1.23-Acre Soundfront Lot With 147 Ft. Of Private Beach. Sale Includes 1.08 Acre Abutting Building Lot To The North, Totaling 2.31 Acres, Offering Privacy On Secluded Cul-De-Sac Location. Vaulted Ceilings, Open Common Space, Expansive Glass Walls Inform The House W/Stunning Light & Water Views. Professional Eat-In Kitchen, Wood Burning Fireplace, In-Ground Pool, Gracious Master Suite, 5

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.

860 Diedricks Rd, Orient

4 Beds, 5 Baths, 3,450 SqFt
This Newly Constructed And Methodically Laid Out 3,450+ Square Ft Modern Farm House Boasts 4 Bedrooms, 3 Full Baths, 2 Half Baths And A Salt Water Swimming Pool Outlined With Blue Stone Copping. Envisioned For Entertaining; Features Include A Gourmet, Eat-In, Chef's Kitchen Featuring Cambria Quartzite Counter Tops With Solid Custom Wood Cabinets And An Open Concept Living Room Complete With 17 Foot Ceiling And Double Height Slate Gas Fire Place.

196 Willow Terrace Ln, Orient

3 Beds, 2 Baths, 1,704 SqFt
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 Upper Deck. 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 & Outdoor Shower, Brick Grill, Copper Gutters &

1700 Youngs Rd, Orient

5 Beds, 3 Baths, 2,800 SqFt
Grand Waterview Cedar Shingled Craftsman Only Steps From The Long Island Sound. 5 Bedrooms, 2 Baths. 2 Fireplaces, Kitchen, Dining Room And Huge Porch Overlooking The 1.4 Acre Park Like Grounds Perched Above The Long Island Sound A Short Distance Away. Convenient To Everything.

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.

605 Latham Ln, Orient

5 Beds, 4 Baths,
Meticulously Remodeled Contemporary In Beautiful Orient With Endless Views Of Both The Bay And Sound.Close To Bay Marina And Orient St. Park. High End Details Throughout This 5 Br 4 Bath Home Include, Security System W/Camers, Centralized 5 Zone Audio System, Apple Tv 3 Zones. Plenty Of Room For Friends And Extended Family To Enjoy Themselves While Taking In The Beautiful Views.

170 Bay Ln, Orient

4 Beds, 2 Baths, 1,800 SqFt
Quintessential Early 20th C Bay Front Baybreeze Cottage Located On Coveted Bay Lane In Orient Village. .235-Acre Lot, 83.2 Ft. Of Private Bay Frontage, 4-Bedrooms, 2 Full Baths ,1-Car Free Standing Garage. Electric Car Charging Station. Outdoor Shower. Fabulous Views Of Orient Harbor & Yacht Club From The Front Porch & Second Floor Bedrooms.

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.

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.

1695 Greenway E, Orient

4 Beds, 4 Baths, 3,900 SqFt
Amazing Custom Built Home In Green Acres. 3800 Sq/Ft Of Living Space W/ Gourmet Kitchen: All Viking Appliances. First Floor Master Bedroom W/ Oversized Walk-In Shower & Soaking Tub. Open Living Concept Between Kitchen And Lroom. Separate Den & And Formal Dining Room. Second Floor Features 3 Large Bedrooms, 2 Full Baths And Bonus Room Above Garage. Giant Arborvitaes Line Entire Back Section Of The Property Surrounding In-Ground Swimming

560 Grandview Dr, Orient

4 Beds, 3 Baths, 2,856 SqFt
Charming, Victorian Style Home On 1-Acre In Grandview Estates Designed For Easy Entertaining. Relax On The Wrap Around Porch & Entertain In Large Open Common Area Which Opens Onto Rear Deck. Gracious Entry Hall & 2nd Floor Landing, Wood Burning Fireplace In Living Room & Master Bedroom, Hard Wood Floors, 1st Floor Bedroom, Back Yard Deck, 2nd Floor Balcony Off Master & 2nd Bedroom, Cac, Central Vac, Full House Generator, Room For

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.

650 Three Waters Ln, Orient

3 Beds, 4 Baths, 2,300 SqFt
Contemporary Home In Orient By The Sea, Built In 2002. 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.



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.

The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers' personal, non-commercial use.

Information Copyright 2018, Multiple Listing Service of Long Island, Inc. All Rights Reserved.