ML# :3466461 Beautifully converted 19th C Barn - three story residence with 4 bedrooms, 3 full baths, Eat-in kitchen, deck off living room with sound views, and private beach access. Apr $5, 000; May $5, 000; June $8, 000; July $15, 000; Aug $15, 000; Sept $10, 000; Oct - Mar $4, 000/mo; yearly $6, 500/mo. Permit# 0774.
500 Stephensons Rd, Orient, NY, 11957
ML# :3529667 Spacious and grand, historic Terry Mulford House C. 1716, set on 5.8 private acres, fully renovated, with 5 bedrooms and 4 new full baths. New eat-in kitchen, living room with piano and flat screen TV. Relax on the wrap-around porch or rear courtyard. A short trip to Orient and Greenport Village, Orient State Park, marinas, sound, and bay beaches. Price includes all utilities, mid-term, and departure housekeeping. Offered May $9, 000; June $13, 000; July $15, 000; Aug $15, 000; Sept $10, 000; Oct $4, 000; yearly $3, 500/mo. Permit #0667.
30675 Main Rd, Orient, NY, 11957
ML# :3542413 Lovely, sunlight filled ranch in Orient by the Sea private community. Stellar vacation location just 4 houses from the community’s gorgeous private LI Sound beach. Eat in Kitchen, Dining & Living rooms, Ensuite primary, 2 add’l bedrooms & 2nd full bath. Front & back porches and spacious yard. Nearby Orient State Park offers miles of hiking, cycling trails, birding, wildlife viewing and a miles-long, sandy Bay beach. Rental permit # 1100 exp. 3/25/2026.
990 Three Waters Lane, Orient, NY, 11957
ML# :3527836 Step into summer in Orient this year. Relax and rejuvenate in the quiet soundfront beach community of Orient by the Sea. Sunny open concept floor plan incudes glass doors that lead out to the covered backyard deck and invites indoor and outdoor entertaining. Just a short drive away to Greenport’s many restaurants, the area’s popular wineries for a tasting. Or enjoy a bike ride to Orient Beach State Park for a peaceful day on the bay. MD-LD $20, 000 June $5, 000, July $8, 000 Aug $10, 000 Permit #0863
370 Uhl Lane, Orient, NY, 11957
ML# :3501346 Orient Village- Located in Orient at 944 Youngs Avenue, on a private country lane sits this perfect country cottage, oh so close to Orient’s favorite Youngs Road Beachfront. 3 bedrooms and 2 full baths, lovely outdoor deck, yard and overlooking a flower farm and just down the street from Village lane, the Orient Country Store and the Jitney. August $14K RP# 907
944 Youngs Rd, Orient, NY, 11957
ML# :3547141 Magical 1840’s Cottage in Browns Hills with endless views across Orient Bay. Beautiful south facing garden abutting farm fields. Three bedrooms 1.5 baths, outdoor shower, deeded sound beach. A private, tranquil natural sanctuary in bucolic Orient. Offered July $15, 000; Aug $15, 000; Sept $8, 000; year-round, furnished starting Sept $3, 200/mo. Permit #0308.
555 South View Drive, Orient, NY, 11957
ML# :3533473 This modern custom-built home, spanning 4200 square feet, is a masterpiece of architectural design, meticulously crafted with thoughtful details at every turn. Situated in the serene landscape of the North Fork, this property boasts breathtaking views that will captivate and inspire. Upon entering, you’re greeted by an open pavilion like great room maximizing natural light and panoramic vistas. The interior features sleek lines, high ceilings, and premium finishes, creating a contemporary yet inviting atmosphere. The kitchen is a chef’s dream, equipped with state-of-the-art, energy-efficient appliances that make cooking a joy. With ample counter space, custom cabinetry, and a spacious island, it’s perfect for both intimate dinners and entertaining guests. The tranquility of the North Fork surrounds this home, offering a peaceful retreat from the hustle and bustle of everyday life. Whether you’re lounging on the expansive patio, taking a dip in the pool, or strolling down to the Long Island Sound, you’ll find serenity and relaxation at every turn. Beyond the property’s boundaries, the North Fork offers an array of attractions to explore. From stunning beaches and charming farms to world-renowned vineyards, fine dining establishments, and boutique shopping, there’s something for everyone to enjoy. This architectural gem combines luxury, functionality, and natural beauty to create an unparalleled living experience. Whether you’re seeking a tranquil retreat or a sophisticated entertainer’s paradise, this custom-built home is sure to exceed your expectations.
290 Windward Rd, Orient, NY, 11957
ML# :3545613 Stunning Waterfront shingle style home overlooking Long Island Sound. Private beach access. Waterview, heated pool. Wrap-around porch. Original beach stone fireplace, vintage beadboard walls, large, updated gourmet kitchen, open common area, 5 bedrooms, 3 bathrooms, large master ensuite with private screen water view balcony. Beautiful interior furnishings, with teak rocking chairs, chaise lounges and picnic table on porch and pool area for entertaining. Close to Orient Village amenities, marinas, Country store, Yacht Club, and bay beaches. Offered Aug-LD $55, 000; Sept 5-30 $25, 000. Permit# 1108.
2100 Youngs Rd, Orient, NY, 11957
ML# :3538278 Spacious & immaculate Sound front Contemporary home sitting on a hilltop in Orient, overlooking Long Island Sound to the north & farm fields to the south. Meticulously renovated & professionally designed 4 bedrooms, 5.5 baths with 128 ft of private beach. The ground floor has a large family room with glass doors to a blue stone patio, lawn, & stairs to the beach. This level includes an ensuite bedroom, additional full bath, Malm fire drum, & infra-red sauna. The main floor offers an open floor plan with living/dining/den/kitchen, a 2-sided fireplace, new kitchen, new baths, waterside & farm view decks. A professional ping-pong table, CAC, & outdoor shower are additional amenities. The panoramic Sound and farm views on 1.84 acres offer unique privacy. Offered July 65, 000; Aug 75, 000. Permit# 1059.
1390 Demarest Rd, Orient, NY, 11957
ML# :3537227 Impeccably restored and updated 1850’s Farmhouse in the heart of Orient Village. Featuring a great room with open floor plan - gourmet kitchen/dining/living room, a second-floor master bedroom with sitting room, full bath, and walk-in closet for a total of 3-bedrooms 2.5 baths in the main house. There is a separate Cottage with kitchenette, bedroom, and full bath, perfect for guests. Lovely private grounds with gardens, grand lawn, and heated salt water gunite pool. Walking distance to all village amenities, beaches, and marinas. Offered June $20, 000; July $45, 000; Aug $45, 000; Sept $25, 000. Permit # 1019.
400 King Street, Orient, NY, 11957