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.

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.

Beautifully restored and maintained Historic Orient Village Colonial located within walking distance to Orient Harbor, Orient Yacht Club, Country Store & Post Office. Four working fireplaces, one wood stove, original wide plank floors, large, vaulted sunny great room added in the 90’s with wood burning stove, formal dining room with fireplace, master ensuite with fireplace, wine cellar, on-demand natural gas generator, large glass doors open between common rooms and outdoor patio for easy entertaining – and so much more. Grounds include a rear brick patio landscaped with mature specimen trees. House is on the historic registry.

Welcome Home to your Oceanfront Paradise! Nestled along the sun-kissed shores of North Fork’s Orient Point, lies a haven cherished by one family for over two decades. Step into the warmth of tradition, where every sunset paints a new memory, and the rhythm of the waves serenades your soul. With spacious living areas, panoramic views, and direct access to the beach, this oceanfront home isn't just a property; it's a legacy of love, laughter, and endless summer days. As its next chapter unfolds, the owners hope it finds someone who will cherish it as much as they have, someone who will fill its rooms with their own dreams and memories. So, to the next custodian of this cherished home, It’s not just a property being offered but a piece of legacy, love and laughter waiting to be continued. Create your own story in this timeless retreat, where every day feels like a holiday. Where memories are made to last a lifetime. 
Features: One Owner. The offering presents a rare opportunity to acquire at a price point significantly below replacement cost. 
6-BR, 4.5-Baths & Office Room. The High-Ceilinged, Unfinished Basement offers endless possibilities: Entertainment Zone, Game Room, Home Gym, Creative Studio, Golf Simulator, or Wine Cellar. Seller Financing Available. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Attached,

Enjoy spectacular unobstructed vistas of the Long Island Sound from this exclusive 4 bedroom, 3.5 bath beachfront home! Experience coastal living at its finest with your very own private beach, beautiful inground pool and spa - making this the perfect summer retreat for the ultimate in luxury and relaxation. Convenient to all the North Fork has to offer...world class restaurants, vineyards, boating and more! July: $50,000 | August: $55,000 | July-Aug: $105,000

Travel down a private road to a Farmhouse on 2.13 acres of serene. park-like grounds. Featuring living room with wood burning fireplace, kitchen/dining area, 3 bedrooms, 2 full bathrooms, screened porch. Enjoy summer in this quiet, private home near North Fork beaches and amenities. Offered June $9,000; July $15,000; Aug $15,000; Sept $10,000.

Nestled on a private 4-acre lot, with development rights intact, this attractive, 3-bedroom, 3-bathroom historic farmhouse offers the ultimate in privacy. The expansive grounds have already been subdivided into three parcels, providing endless opportunities.

Built circa 1812 by one of the original Orient families, and now lovingly restored, this home masterfully combines classic elegance with modern amenities, such as striking wood beam ceilings with original pegs and hand-made nails and original pine floors, all offering a glimpse into the home’s storied past. The spacious family room with kitchen has a huge wood-burning fireplace and French doors leading out to a large bluestone patio area and the heated gunite pool, perfect for entertaining. The first level also includes a wonderful dining room, plus a parlor with a second wood-burning fireplace and also a full bathroom. The original staircase leads to the second floor and a large, bright hall off of which is the primary bedroom and bathroom.  There are two additional, generously sized bedrooms and a bathroom in the new addition to the house.

Set amidst mature trees and beautifully landscaped, the property is completely fenced in and lined with hedges for ultimate privacy.  The large barn which sits majestically on the property was built in 1925 using reclaimed lumber from a ship which washed up nearby, and adds versatile space for a variety of uses.  Located just moments from Orient Village and its surrounding beaches and farm stands, this peaceful retreat has it all, whether a full-time residence or a fabulous weekend haven.

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!

Back Yard, Historic District, Near Public Transit, Near School, Near Shops

Abutting  16 acres of picturesque vineyard, this stunning contemporary home offers a rare blend of natural beauty and modern potential. Surrounded by lush, mature landscaping, the property features a sparkling in-ground pool with breathtaking vineyard views stretching to the east—an idyllic setting for relaxation and entertaining. Step inside to a dramatic Great Room with soaring ceilings, setting the stage for a bright and airy living space. The flowing layout includes an eat-in kitchen, a formal dining room, and endless opportunities for personalization to make it your own. Upstairs, the second level features two inviting guest bedrooms with a shared full bath, while the spacious primary suite boasts vaulted ceilings, elevated vineyard views, and a generous en-suite bath. Beyond the home, experience the best of North Fork living with exclusive access to Truman Beach, charming local farms, world-class fishing, and renowned farm-to-table dining. Don’t miss this incredible chance to create your dream retreat in the heart of wine country!

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.

This exceptional property, once a Victorian firehouse built by Captain Vail in the 1800s, was replaced in 1938. The current owners have made thoughtful and significant upgrades, providing a rare opportunity for the discerning buyer to own a piece of history in coveted Orient Village. This historic firehouse residence stands proudly on Orchard Street, surrounded by beautifully planted, intimate gardens that create a private sanctuary.
Set behind a hedge just steps from Village Lane, the property is flanked by specimen trees and shrubs.  Meandering blue stone and slate patios, ornamental grasses, perennials, and an open lawn area lead to an outdoor shower and storage shed. From the garden, a wide staircase ascends to expansive mahogany decks and large screened porch on the second floor, offering water views and incredible sunsets. The second story decks are accessible directly from the newly renovated, light-filled chef's kitchen, creating an inviting space for dining and entertaining. The kitchen features Chefs appliances, ample storage, and plenty of counter space, making it ideal for hosting guests as you prepare meals. Whether dining inside in the spacious dining area, which easily accommodates dinner for 16, or on the deck, you’ll enjoy the perfect setting for every occasion.
Inside, the home boasts soaring 12-foot ceilings and an abundance of natural light flooding through large windows and an open floor plan. This coveted residence offers ample opportunities to personalize your living space to suit your lifestyle. The two-story home spans over 4,000 square feet, with four bedrooms and four full bathrooms. The ground level features an open living area with four sets of French doors leading to the lush garden, an open living area, three additional bedrooms, and two ensuite bathrooms and laundry. The attached garage and a second utility kitchen completes the first floor.
On the second level, you’ll find a large, light filed open floor plan with a large dining room and chef's kitchen, and plenty of space  for grand entertaining. Just off the open floor plan is a den, the primary bedroom suite which includes, a spacious ensuite bathroom, and a large walk-in closet that opens to a private screened porch and mahogany deck.
With its unique blend of historic charm and modern finishes, this property offers an extraordinary living experience located in one of the area's most desirable locations; ideally positioned near Village Lane, just steps from The orient country store, historical society campus, yacht club, marina, lovely shops, as well as nearby beaches and the jitney . All of this is set within the close-knit, highly sought-after Orient Village community that is truly one of a kind.

Entertain poolside in this stylish Mid-C Modern set on 2 acres, with views of Orient Harbor & the Sound. Handsomely furnished with master bedroom with full bath plus 2 additional bedrooms & full bath, large gourmet kitchen, den, spacious living room/dining room/common space opening to wrap-around deck overlooking pool. Walk to Village, Latham's farm stand. Aug $35,000. Permit# 0321.

Nestled on 2.84 acres of picturesque land, this stunning 1867 farmhouse offers the perfect blend of historic charm. With 7 spacious bedrooms and 3 full baths, this expansive home provides ample room for a growing family or anyone seeking a peaceful retreat.

Step inside to discover original details like hardwood floors, high ceilings, and charming built-ins that evoke the farmhouse's rich history. The heart of the home features a cozy living room, formal dining area, and a large kitchen that's ready for your personal touch.

The standout feature of this property is the former schoolhouse, beautifully converted into a light-filled art studio. Whether you're an artist looking for the perfect creative space or someone in need of a private office, this versatile building adds endless possibilities.

Outside, you'll enjoy the serene beauty of the surrounding property, with plenty of room for gardens, outdoor entertaining, or simply unwinding in nature. While the home offers privacy and space, the nearby community beaches provide a perfect spot for swimming, picnicking, or simply enjoying the waterfront lifestyle.

This one-of-a-kind home offers an incredible opportunity to own a piece of history while enjoying modern comforts and endless potential. Don't miss out on the chance to make this farmhouse your own! Being Sold As is.

Orient, The Hill. Perched high on a hill above the Long Island Sound, is this exceptional offering in the coveted "The Hill" historic estate enclave. Authentic, classic, grand. Architectural details include 5 fireplaces, 16/1 windows, front entry door with sidelight panes. Beautiful landscape, hardscape, paths and plantings adorn this rolling 1.3 acre property. Swimming pool. 6 bedrooms 4.5 baths. Generous size rooms and waterside screened porch. Stunning sunsets. Owned by the same family for 65 years. The next one could be yours.  A truly special Orient property. The possibilities are endless. Set above the stretch where the Sound meets the Bay, it doesn't get any more North Fork than this!

Part Wooded, Private, Sloped, Sprinklers In Front, Stone/Brick Wall

Stunning Orient retreat with a private heated gunite pool; enjoy an ideal location with a beach and village just down the block. This tranquil home features soaring ceilings, two fireplaces, four ensuite guest rooms, a private office, an enormous eat-in kitchen, a light-filled dining room, a hotel-like master suite with a second-floor balcony, charming front porch, two living rooms, and beautiful design details at every turn. This home is as stylish as it is comfortable and is the perfect summer rental to host family and friends. Mature trees and landscaping dots the exterior with a large outdoor shower. Garage with flex rec room space. Plenty of parking. Just minutes to Greenport Village and all the best amenities Orient and the North Fork has to offer. Aug-LD ren:45000, July ren:38000, June Rented

A rare opportunity to acquire one of Orient's oldest operating farms, held in the Terry family since 1730.  The farmhouse was built by Marcus Terry in 1850 and operated as the Orient Point Post office until 1913.  A large barn with loading dock and original outbuildings complete the offering.  Development rights for 14.4 acres have been sold, with development rights intact for an additional 5 acres.  There are sound beach rights.

Very spacious, sunlight filled custom built beauty just 3 minutes to gorgeous, private community LI Sound beach.  44' x 24' heated, saltwater pool. Bright & airy open concept design LR/DR/KI with sliders to expansive deck overlooking private, fully fenced, park-like grounds. Upstairs has a large, 2nd living room with billiards, foosball, large tv plus sliders to private deck. 2 primary ensuites  - one on each level.  2nd floor primary has its own entrance, living room, wet bar, refrigerator and wall of sliders to deck. Home is impeccably maintained and tastefully furnished throughout. Fine dining, marina & state park and Cross Sound Ferry just down the road.  A scenic 9 mile drive to Greenport with its fine dining, cafes, waterfront park, boutiques & galleries, golfing and more. Rental Permit #1117. Exp. 5.6.26.

Level, Sprinklers In Front, Sprinklers In Rear

STUNNING ORIENT WATERFRONT PROPERTY WITH CHARMING CAPE HOME – TWO LOTS BEING SOLD TOGETHER.
This unique property offers two parcels of land, blending the serene beauty of Orient with the comforts of a Classic Cape-style home. 
The 1.75-acre waterfront lot, features access to a shared gazebo on a tranquil creek that leads out over the meadow to your own private beach, and has stunning views of Orient Harbor. This scenic setting offers peace and privacy, making it a perfect retreat. 
 Across the street sits a charming 1940s Cape-style home with panoramic Waterview’s.  The first floor features a large living room with a wood burning fireplace, perfect for relaxing, formal dining room, a delightful three-season room with picturesque views, spacious kitchen with ample counterspace, a first-floor bedroom and full bath for added convenience.
Upstairs, you will find three more bedrooms, each offering ample space and natural light and Waterview’s, along with a full bath. Hardwood floors throughout the home add to the charm and character. 
This property offers a rare combination of waterfront living, charming history, making it an ideal escape or family home.
 Additional information: Location Features:Protected Wetland,Separate Hotwater Heater:Y

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.  Available July $8,000; August $9,500 2025 RP# 907

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