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120 Lands End Rd, Orient

4 Beds, 4 Baths,
Getaway to the North Fork and relax in this gorgeous Orient Point vacation home. Designed to capture the vast water views, this one has it all: 4 large bedrooms, large outdoor entertaining spaces, in-ground pool, jacuzzi, outdoor shower, water views, room to play and a gorgeous Sound beach at the end of the road. Close to dining, marina, state park, Greenport and more. Frequent repeat tenants; don't miss out on this one! Available Aug. 2-16 and

1010 Village Ln, Orient

1 Bed, 1 Bath,
Private apartment on historical Village Ln. in the heart of Orient Village. Features living room with 2 sofas that can become single beds, dining area, kitchen, 1-bedroom with queen bed, full bath, private garden. Pass to Truman's Beach. Walk to amenities, bay beach, Yacht Club, marina, farm stands & Jitney to NYC. Apr $2,400, June $3,000, Aug $5,000, Aug-LD $5,500, Sept $3,000, Oct $2,400

38195 E Main Rd, Orient

3 Beds, 2 Baths,
Enjoy the summer in charming Orient Point. Sunny & spacious expanded ranch features 3 BR, 1.5 baths, Eat in kitchen, formal dining & living rooms, office and large den with sleeper. Sliders to wrap deck facing fenced yard with country views. Minutes to Orient Beach Park (seasonal pass available) & popular restaurant. Owner open to shorter stay - minimum of 2 weeks. Cleaning fee additional. May consider house trained dog with

20615 Main Rd, Orient

3 Beds, 3 Baths,
Stunning Bay Views And A Spacious Light Filled Mid Century Home Offering In 3 Bd 2.5 Baths, Living Rm, Fireplace , Dining Room, Kitchen, Sunroom, Master With Bath En Suite And Walk In Closets. Wonderful Summer Or Fall Retreat, Bay Front Access.

790 Oyster Ponds Ln, Orient

3 Beds, 1 Bath,
Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored Village home on landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney to NYC. Available June $6,000; July $7,500.

22495 Main Rd, Orient

3 Beds, 2 Baths,
Charming 300-year-old Orient landmark home, impeccably restored & exquisitely equipped. Close to all Village amenities, NYC Jitney & beautiful Youngs Rd. Sound beach. House is surrounded by lush gardens and specimen trees. Guest pass to Truman's Beach.

925 Orchard St, Orient

4 Beds, 2 Baths,
Orient Village- Escape To The North Fork And Spend An Idyllic Vacation In This Newly Restored Historic Home On A Beautiful private 1 Acre Property with heated Pool, Just Down The Street From Orient Harbor. Inside- Is A New Gourmet Kitchen, Great Room With Dining, Living Room W/Fireplace, Den And 4 Bedrooms With 2 New Ensuite Lux Baths.. For Entertaining & Relaxing- A Large Outdoor Deck & Wrap Around Porch W/Nice Outdoor Furnishings. This

1055 Soundview Rd, Orient

3 Beds, 3 Baths,
Sun, Sand, Relaxation & Privacy...Have It All At This Beautifully Renovated Orient Soundfront Home With Waterside Pool And Expansive Deck For Entertaining, Including All New Furniture. Enjoy Panoramic Waterviews, Private Steps To Beach And Remarkable Sunsets! $8,000/week June, $12,000/week July & August, strictly 2 week minimum.

1135 North Sea Dr, Orient

2 Beds, 1 Bath,
Retreat and relax in this updated summer beach cottage by the sea with heated 20 x 40 in-ground salt water pool. Beach rights to association sound front beach just a few blocks away. June 15-30 $5,500, July $12,000 Aug 1-15 $6,500

560 King St, Orient

3 Beds, 2 Baths,
Wonderful mint condition 3 bedroom ranch, a bike ride to Orient Village, beaches, farm stands & marinas. Private rear garden, deck, gas grill, outdoor shower, open common space. Perfect for entertaining. Available Aug $10,000; Aug-LD $12,000.

590 Winward Rd, Orient

4 Beds, 3 Baths,
Orient waterfront home set on an acre of land with private beach features break taking water Views of the sound from both floors, balconies and all rooms. This European inspired home offers a fully Equipped Gourmet Kitchen, oversized dining room, Living Room, family room, office, 4 bedrooms and 3 full baths. Enjoy the privacy, tranquility, views and convenience to transportation, dining, vineyards and more. 2 miles to Orient ferry, 7 miles to

805 Navy St, Orient

4 Beds, 3 Baths,
Newly renovated Orient Village home complete with 20X40 pool. This stylish getaway features an open floor plan and gourmet kitchen with high end appliances, wine Cooler, wood burning fireplace and large outdoor entertaining area with grill, fire pit and pool lounge. Minutes from Orient Yacht Club, shops, and beach. The perfect north fork summer getaway! Goes quick every year, don't delay!

1970 Village Ln, Orient

3 Beds, 3 Baths,
Enjoy summer in the crown jewel of Orient Village. Restored & meticulously maintained with original exposed beams, wide-plank floors, period hardware, 3 updated wood burning fireplaces, custom cabinetry & woodwork. 2 large decks span the back of the house overlooking Orient Harbor & Yacht Club. June $14,000; July $22,000

530 Orchard St, Orient

3 Beds, 3 Baths,
Mint condition exquisitely restored 18th C home in coveted Orient Village. Main house has 3 bedrooms, 3 baths, gourmet kitchen, formal dining room, central air, private rear manicured garden overlooking open fields with hot tub & newly installed in-ground pool. Close to Orient Yacht Club, post office, Country Store & other village amenities. Additional bonus space with gym, writing studio, outdoor shower, and so much more. Available

1800 Village Ln, Orient

3 Beds, 3 Baths,
This Charming Village House Is One Of Orient's Premier Historic Homes. Sweeping Views Of Orient Harbor, Wide Planked Floors, Chic Interior Design Blending Old World Backdrop With Modern Interiors . A Very Special Listing For The Sophisticated And Discerning - Bike To Beach. First Floor Master With Fully Renovated Bathroom. A Summer's Dream.

1045 Orchard St, Orient

3 Beds, 3 Baths,
Enjoy July at this stunning Orient Village expertly designed and restored c 1860 classic Long Island farmhouse that reflects how we live and entertain today. Renowned Architect Elizabeth Robert's design and aesthetic's interwoven spaces, celebrating the historic with the unexpected, creating beautifully connected living spaces. Chef's kitchen, cooking rumford fireplace, Great room, 3 bedrooms with 2.5 baths, CAC, new heated in-ground pool, set



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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