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$4,000,000
6 Beds ⋅ 7 Baths ⋅ 918863 MLS
This Sound Front home at the edge of a quiet Orient cul-de-sac is more than a haven-it's a destination for those who appreciate the rare union of luxury, privacy, and personality. Here, drama is found in the sweep of panoramic water views and the hush of mornings on a private deck, just upstairs from your own sandy shoreline. Step into soaring, sunlit spaces designed for living boldly: a cathedral-ceilinged great room crowned by a Niamh Barry light sculpture, six uniquely serene bedrooms, and a media lounge fit for both celebration and retreat. Two grand spiral staircases anchor the heart of the home, while an elevator ensures every level is effortless. This is a house that thinks ahead-10-foot ceilings, custom red oak flooring, radiant heat where you want it, a climate-controlled wine room, a butler's pantry for flawless entertaining, and double laundry rooms for seamless living. Outside, a 34'x13' Gunite heated infinity pool and 8'x8' spa blend into Sound views, with private stairs leading to the beach for spontaneous escapes. Security, comfort, and modern ease are ever-present with remote cameras, central vacuum, a triple-car garage, a full-house generator, and avant-garde HVAC and audio systems-leaving you free to focus on what really matters: sunrises, open water, and time well spent. For those who believe a home should never feel ordinary-this Orient retreat awaits.

2670 Grandview Drive, Orient
$3,625,000
3 Beds ⋅ 4 Baths ⋅ 876008 MLS
This stately Dutch Colonial sound front, is the perfect blend of privacy, luxury and natural beauty. Sweeping water views, with generous interior and exterior living spaces that flow seamlessly. Warm rich natural wood finishes, multiple bedrooms, a den, a second floor loft, A private pool, leading to your outdoor patio, garden and stairs to your beach. Top it all off with a Full finished basement, gym, and an oversized two car garage. This is a must see!

215 Hillcrest Drive N, Orient
$3,150,000
3 Beds ⋅ 3 Baths ⋅ 924682 MLS
Designed by celebrated architect Richard Gluckman, this contemporary waterfront residence sits along one of Orient’s most coveted stretches of coastline in the enclave of Browns Hills. Perfectly positioned for privacy on a generous 1.25-acre lot, the land’s natural elevation affords sweeping Long Island Sound views from nearly every room. A great room with soaring ceilings and a wood-burning fireplace anchors the main level, flowing seamlessly into the kitchen and adjacent dining area—ideal for entertaining. The eastern wing features an en-suite bedroom, well-positioned as a quiet respite for guests. Upstairs, the primary suite includes an en-suite bath and a separate office providing additional flexible space. The expansive grounds offer ample room for a pool or future expansion and are home to a diverse array of birdlife and native plantings, enhancing the tranquility of this coastal retreat. Across the rolling lawn is access to a private beach for sunsets, swims, and picnic dinners. Ideally located minutes from Orient and Greenport Villages and the Cross Sound Ferry to New England, this is a rare opportunity to own a thoughtfully designed modern home in one of the North Fork’s most desirable settings.

900 N View Drive, Orient
$2,350,000
3 Beds ⋅ 4 Baths ⋅ 855576 MLS
Custom built contemporary home on coveted Narrow River Road in Orient. Unparalleled panoramic views of Peters Neck, Orient Harbor, Orient State Park and Long Beach. Three bedrooms, 3.5 baths, media room, office, open common space, gourmet kitchen, upper and lower water view decks.

305 Narrow River Road, Orient
$2,140,000
3 Beds ⋅ 3 Baths ⋅ 982490 MLS
The crown jewel of Orient Village, the Shaw House/ Revolutionary Cottage was built in 1730 and features 3 bedrooms, 2.5 baths, and an updated eat-in kitchen. Original exposed beams, wide-plank floors, period hardware, 3 updated wood burning fireplaces, custom cabinetry & woodwork. Two large decks span the back of the house overlooking Orient Harbor & Yacht Club. Located in the heart of Orient Village walking/biking to all village amenities. 48 hr notice for showings.

1970 Village Lane, Orient
$2,100,000
3 Beds ⋅ 3 Baths ⋅ 997654 MLS
Set in the heart of Orient’s bucolic Browns Hills, this light-filled contemporary residence offers an exceptional blend of privacy, design, and landscape. Expansive views stretch across open pastoral fields to the bay beyond, creating a setting that feels both peaceful and uniquely North Fork. Spanning three levels, the home features a highly functional floor plan with three bedrooms and three baths, thoughtfully arranged to provide flexibility and comfortable separation of space. Large windows and multiple exposures fill the interior with natural light while framing the surrounding scenery throughout the day. Outside, beautifully developed landscaping surrounds a heated saltwater gunite pool, expansive decking, and outdoor shower, creating an ideal environment for entertaining or quiet summer living. Association access to your Sound Beach completes the offering, adding easy waterfront enjoyment to this serene Orient retreat.

255 S View Drive, Orient
$2,100,000
4 Beds ⋅ 5 Baths ⋅ 828111 MLS
Here's a stunning new construction home, part of a thoughtfully designed series that blends quality craftsmanship with modern convenience. Wide oak floors set the stage for an open floor plan, where a professional kitchen with oversized island flows into a spacious dining area and beverage bar - perfect for beach house gatherings. The living room in anchored by a cozy fireplace with built in bookcases, creating an inviting space to gather after a day biking and experiencing the hiking trails. Designed for comfort, the main level features a primary suite, along with a mudroom, laundry room, and a covered back porch overlooking a beautifully contoured yard. Upstairs, an open sitting/office room adds another cozy retreat, accompanied by a secondary primary suite, two additional bedrooms and a full bath. Need even more space? The finished basement with an outside entrance offers a full bath, ideal for media room, gym or home office. Located in the private Orient By The Sea beach community, this home offers access to miles of beach, scenic picnic spot with grilling and tables and some of the best sunsets over the water on the North Fork. Adjacent to Orient Beach State Park , you'll have easy access to a playground, nature trails, a popular summer concession stand, even kayak rentals. Plus, the charter fishing boats, Orient Point Ferry with access to Foxwoods Casino and entertainment 20 minutes off the New London Ferry, entertainment options abound.

655 N Sea Drive, Orient
$1,900,000
4 Beds ⋅ 4 Baths ⋅ 956958 MLS
Treat yourself to the astounding panoramic waterviews afforded by this feature-rich luxury home set in the most-easterly enclave on Long Island’s beautiful North Fork. From the full-length living-level deck, Long Island Sound and the Connecticut shoreline beckon to the north; east and south are striking views of Plum Island and Gardiners Bay. Passing through stone pillars and an arched privacy gate, you will first behold this handsome spectacularly built home over the length of the vast brick driveway. Designed and crafted without regard to expense, the home’s deft use of space and robust construction maximize the remarkable water views, provide gracious living spaces, and yield exceptional pride of ownership. Lavish with amenities, including three fireplaces, Viking chef’s kitchen, and a cherry-panelled elevator, it is set on tastefully landscaped grounds of nearly an acre, with ample room for a large pool and tennis. Come home soon!

1680 Lands End Road, Orient
$1,800,000
4 Beds ⋅ 3 Baths ⋅ 844387 MLS
STYLISH & TRANQUIL: This designer's own home overlooks protected wetlands with panoramic views towards Orient Harbor and Hallocks Bay. The interior and exterior are repleat with custom architectural details. Ground floor open plan with living room, dining room and gourmet kitchen boasting Viking range, Sub Zero fridge and Bosch dishwasher. Imported terra cotta tile floors throughout, tumbled marble countertops. Rais wood burning stove ties the space together with flame view window. Also on ground floor, 2 bedrooms, 1.5 baths, mud room, ample screened in porch and extensive exterior decking. Upstairs primary bedroom with ensuite bath & dressing, additional bedroom/office and 2 working art/craft maker spaces with great natural light and access to back yard stairs to gunite, heated, salt water pool with bluestone patio and coping, outdoor shower & dining areas. Attached 2 car garage, whole house generator, full irrigation system. Very private fully fenced back yard. Wrap around cedar deck. Very close to Potato Dock & Orient Harbor beaches as well as all that Orient Village has to offer.

1075 Narrow River Road, Orient
$1,751,620
3 Beds ⋅ 2 Baths ⋅ 845202 MLS
Beautifully restored & maintained 18th C Village classic home located on coveted Village Lane in the heart of Orient Village. Private access to abutting open space of Poquatuck Field Park provides pastoral field and bay views in perpetuity. The home offers 3 bedrooms, 2 full baths, 2 fireplaces, and a gourmet kitchen that opens onto the dining/family room and 3-season screened sunroom. The 1,924 sf home features a ground floor master bedroom, full bath, pantry, laundry, mud room – offering the convenience of one floor living. The second floor has 2 additional bedrooms and a full bath. Included are two accessory structures – a vintage workshop, 1.5-car garage, and rear & side garden brick patios. Features include CAC, a new state-sanctioned septic system, new roofing, new cedar shingle siding on the south & east facing sides of the house, new driveway, and new brick back patio. Located walking distance to NYC Jitney, Country Store, post office, Yacht Club, marinas, bay and sound beaches. See the attached improvements list for more detail.

1620 Village Lane, Orient
$1,450,000
4 Beds ⋅ 4 Baths ⋅ 932673 MLS
Orient By The Sea — Sound front community with a deeded association beach and park. Two story, 4 bedroom, 3 1/2 bathroom Nantucket style residence in sought-after Orient By-The-Sea. Perfect for year-round or vacation living. Covered mahogany wrap porch welcomes you to this light, open and spacious home that is perfect for entertaining, holiday gatherings, and cozy family time. Living room, great room, formal dining room, large kitchen with informal dining area. Wooden floors, light-filled. Great room has a vaulted ceiling and floor to ceiling gas stone fireplace and hearth, huge windows and transoms. Great room opens to gracious rear covered porch with ceiling fan and skylights, providing shade and "cover" while also permitting natural light. Great room, kitchen, and porch overlook the gorgeous level rear yard. This home features two spacious primary ensuite bedrooms, one on the main level and a second primary ensuite on the second level. A laundry room and powder room complete the main floor. A balcony walkway overlooks the great room from the second floor. Primary ensuite, two additional bedrooms and a full hall bathroom with an additional bonus space with windows and skylights complete the second floor. Attached two-car garage. The level shy acre property offers a serene, private landscape of lawn, mature specimen plantings and plenty of room for a swimming pool. The Cross Sound Ferry, Orient State Park, and Duryea's Restaurant are close by. The beautiful, well-maintained association sound beach, with a stone path, picnic area, and brick barbecue is just around the corner. A very special opportunity to live and enjoy life on the North Fork, from a coveted Orient location.

815 Uhl Lane, Orient
$1,260,000
4 Beds ⋅ 2 Baths ⋅ 965468 MLS
Rare and truly spectacular, this protected water view setting is one of Orient’s most exceptional offerings. Perched atop the historic hill of the former Mount Pleasant Hotel — once a beloved East End vacation retreat — this remarkable property captures the very essence of North Fork coastal living. Set on 2.87 acres (.87 on Munn Lane combined with 2.0 acres at 20400 Main Road) stretching from Munn Lane to the shoreline of the Great Peconic Bay, the property enjoys sweeping, unobstructed water views — including Bug Light and the Orient Yacht Club — direct bay frontage, and unforgettable sunrises and sunsets that paint the sky in every season. Originally dating to the 1940s, the spacious, quintessential North Fork cape-style home offers 4 bedrooms and 2 baths with generous living space and timeless charm, plus a walk-out basement with garage providing storage, workshop space, or future finishing potential. Whether you envision restoring its classic character, thoughtfully updating and expanding to maximize the panoramic views, or creating a waterfront compound, the setting offers extraordinary flexibility and long-term value. Imagine mornings spent with coffee overlooking the bay as sailboats drift by, afternoons kayaking or paddleboarding from your own shoreline, and evenings gathered with friends for sunset dinners under open skies. With ample acreage and privacy, there is room for gardens, a pool, entertaining terraces, or simply quiet moments surrounded by coastal breezes and the soothing sound of the water. Located in the North Fork’s easternmost hamlet, Orient is cherished for its maritime heritage, preserved farmland, beaches, boating, wineries, farm stands, and ferry access to New England — a peaceful coastal escape sought by buyers seeking privacy, nature, and authenticity. Here, life moves at a different pace — where beach walks, vineyard afternoons, and sunset evenings along the shore become part of your everyday rhythm.

275 Munn Lane, Orient
$1,150,000
4 Beds ⋅ 2 Baths ⋅ 958425 MLS
You have to come back and see this house with me because it’s got that real “grandma’s classic 1940s winter weekend” energy in the best way that has been on the short list feeling. Picture this: it’s snowing outside, and we’re posted up in the big living room with the granite fireplace going. Knotty pine paneling, bookshelves built in on both sides of the hearth, and that warm glow that makes you feel settled. We’ve got Monopoly spread out on the coffee table, a huge bowl of popcorn (the legit kind made on the stove), and a record playing… then playing again… then somehow playing again because that’s what happens in houses like this. And of course there’s always that one person in our group who breaks out a slide projector, vacation slides from back in the day with the vintage clothing, the hair styles, taking in the moments. This house just fits that vibe perfectly. Then you walk into the sunroom and it changes gears: slate floors under your feet, water views straight out toward the beach, and it becomes the reading and lounging zone. Newspapers, magazines, tuna melts, tomato and rice soup. It’s basically the best relaxing room. Outside, it’s the kind of winter that makes you want to actually do stuff: we can go sledding down Munn Lane, then heading to the Causeway beach to see what the sea rolled in, perfect for seaglass collecting. That whole shoreline exploration where you come back with cold cheeks and a pocket full of little treasures. The layout is great too, wood floors through most of the house, and there’s that first-floor bedroom space (or den) with water views across the street that ties the whole country home feeling. It’s cozy, practical, and somehow still feels special. And the garage… three bays, but it doesn’t feel like “just a garage.” It feels like a workshop where projects are always in motion. The kind of place where sleds, bikes, paddleboards, clam rakes, fishing poles, beach chairs, and coolers all have a home. Here’s the kicker: it comes with two pieces of land, including the waterfront property across the street. So those water views? Protected. There’s about 50 feet of sandy beach, and the path to the water is right across the street, perfect for kayaking or paddleboarding in the summer. And sitting on the hill, the elevation is high enough that you’re not sitting stressing about flood issues. In the summer you’re up on the hill watching fireworks in Orient Village, with views from the living room, sunroom, and that main-floor bedroom/den. It’s peaceful, authentic, and it feels connected to the real local story—ice boat racing off Narrow River Road, oyster farming, clamming, fishing… all of it. This is what relaxation looks like when “country” means coastal, classic, and this is what we wanted.

20715 Main Road, Orient
$1,095,000
3 Beds ⋅ 2 Baths ⋅ 953196 MLS
Welcome to this lovely water-view ranch style home in the coveted Orient by the Sea community. A truly inviting home offering the perfect blend of coastal serenity and easy one level living. The front entrance opens to a bright living room with a wood-burning fireplace which graciously flows into the dining area. The eat-in kitchen has stainless steel appliances and connects conveniently to the mudroom and half bath. There are three sunny bedrooms- all with hardwood floors, and a full tiled hallway bathroom. The crown moulding adds a touch of classic detail on the freshly painted walls. A delightful three-season sunroom with authentic wainscoted ceilings, teak floors, and new windows is the perfect space to relax and enjoy the scenic backyard views, relax and read, or dine in style. Additional features include central air conditioning, two-car garage, full basement, and attic—offering abundant storage. This home has easy access to the community beach and park just down the road- a perfect setting for picnics and sunsets by the Sound. Also located close to Orient Beach State Park, Cross Sound Ferry, and the historic village of Orient. Oh, and you will love the low taxes! This home is a true North Fork retreat by the Sound!

350 Soundview Road, Orient
$1,010,000
3 Beds ⋅ 3 Baths ⋅ 849591 MLS
Craftsman style spacious updated 3-bedroom, 3 bath home in coveted Orient by the Sea. A short walk to stunning association sound beach. Private covered front porch, double sided wood burning fireplace in living room and family room, hardwood floors throughout, private rear garden, 2-bay garage with garage door opener, rear deck, shed. Close to Orient State Park.

555 Three Waters Lane, Orient
$968,000
2 Beds ⋅ 1 Baths ⋅ 942303 MLS
Well maintained private home in the beloved Green Acres beach community with sound beach at end of road. .63-acre lot that backs onto 63-acres of pastoral undeveloped preserved land. The home features oak floors throughout, 2 bedrooms, 1 full bath, 1-car garage, and shed. Full second floor bonus space and storage under roof eaves. Close to Orient Village and renowned Orient Beach State Park and Orient Ferry.

65 Greenway W, Orient
$875,000
3 Beds ⋅ 2 Baths ⋅ 879579 MLS
Spacious ranch on large level lot with beautiful mature trees located a very short distance to private association beach on Long Island Sound. Ample room for pool. Three bedrooms, two full baths, open plan kitchen to dining area with wood burning stove. Large living room, full basement, one car attached garage, mud room, hardwood floors and central air conditioning complete the package.

2000 Greenway East E, Orient
$870,000
1 Beds ⋅ 2 Baths ⋅ 848840 MLS
Village Lane charmer located a short walk to the bay and all village amenities. Gourmet kitchen, open common space, wonderfully bright and airy. Second floor master suite with window seat, bedroom, bath, sitting room, and rear balcony. Large accessory 2-story studio. Brick patio/garden connecting house and studio for outdoor dining and entertaining.

1740 Village Lane, Orient
$850,000
3 Beds ⋅ 2 Baths ⋅ 832086 MLS
This charming, well-maintained 3-bedroom, 2-bath Historic Landmark is on coveted Village Lane, a national historic district in the waterfront village of Orient. Known as The Hale House, this enchanting home, with it's handsome wide-plank and hardwood floors was originally built in 1781 and was reputed to be one of the first schoolhouses in Orient. A blacksmith and Justice of the Peace named Francis Young then took possession and in 1932 Herbert Hale purchased it and fully renovated and expanded it to its present state. It has been cherished and updated throughout the years. Just down Village Lane is a bustling General Store with its well-used front porch, the post office, an active Community Hall, Orient Yacht Club, and the wonderful Oysterponds Historic Society complex. Truman's Beach, a candy store, farmstands, wineries, golf, marinas, and Orient State Park are just down the road and the Village of Greenport is 5 miles west. Although you feel like you've time traveled to very special and bucolic place, the Jitney stop from Manhattan and the Ferry to New England are conveniently close by! Truly a delightful, quaint North Fork community!

200 Village Lane, Orient
$830,000
3 Beds ⋅ 2 Baths ⋅ 988496 MLS
Welcome to this meticulously maintained Craftsman home in the heart of Orient. A home where timeless character meets modern, move-in condition. This mint condition 3 bedroom, 2 bath offers a perfect blend of classic architectural charm with bonus modern amenities. Set on a private, landscaped yard, this property offers a serene outdoor retreat. Perfect for relaxing, dining alfresco, or enjoying the peaceful surroundings. Ideally located just moments from Village Lane, pristine Bay and Sound beaches, and Orient's beloved local amenities. This home places you at the center of one of the North Fork's most desirable coastal communities. Whether you're searching fora primary residence, weekend getaway, or investment property, this exceptional Craftsman delivers on location, condition, and lifestyle.

23530 Main Road, Orient
$825,000
2 Beds ⋅ 2 Baths ⋅ 893595 MLS
Charming and private home in Green Acres in Orient Point. Open floor plan with dining room/kitchen opening onto lovely second floor deck. The living room and rear deck have open views of 63 acres of pastoral undeveloped preserved land. Association sound beach down the road.

685 Greenway W, Orient
$770,000
4 Beds ⋅ 3 Baths ⋅ 947427 MLS
Stunning North Fork Colonial in Orient Welcome to your dream home on the beautiful North Fork. Situated on a flat spacious acre with mature specimen trees provide privacy in the desirable community of Orient by the Sea. This post modern residence offers the perfect blend of luxury and comfort with 4 generous bedrooms, including a remarkable 3-room primary suite on the main floor featuring a private sitting room, this home is designed for relaxation and privacy. The great room boasts soaring ceilings and a striking stone fireplace with gleaming hardwood floors and walls of glass fill the living area with natural sunlight and warmth throughout the year. Entertain guests with ease on the wrap-around covered porch, ideal for gatherings and enjoying the tranquil surroundings. The kitchen offers classic wood cabinets, stainless steel appliances and quartz counters and backsplash. As part of a private deeded beach community, you are minutes away from the beach with your own private park area -- pristine beach, kayak launch, swimming, fishing, picnic, entertainment area and outdoor grill. Watch the sunset on the Long Island sound or visit North Fork wineries, world-class golf courses, charming towns and villages, country farm stands, fine dining, shopping and more. Conveniently located near the Orient Point Ferry, Orient Beach State Park and dining, entertainment and marina at Duryea’s Beach Club. Experience the best of coastal living in an area celebrated for its beauty and vibrant lifestyle.

175 Uhl Lane, Orient

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.