Orient Real Estate

Welcome to Orient, New York—a hidden gem nestled at the eastern tip of Long Island in Suffolk County. This quaint hamlet is a picturesque blend of stunning natural beauty and rich history, making it a perfect destination for those seeking a tranquil lifestyle or a weekend getaway.

Orient is renowned for its breathtaking waterfront views, charming farms, and lush vineyards. The area boasts a unique coastal charm, with sandy beaches and serene bayfronts that invite you to unwind and embrace the beauty of nature. The Orient Beach State Park is a local favorite, offering miles of pristine shoreline for swimming, picnicking, and birdwatching, while the nearby Orient Point Lighthouse stands as a historic sentinel overlooking the waters.

The community in Orient is tight-knit and welcoming, with a strong emphasis on preserving the area's natural and historical heritage. You’ll find a delightful mix of local shops, artisanal markets, and cozy eateries that reflect the region's agricultural roots. The Orient Point Ferry provides easy access to New England, making it a convenient spot for travelers and commuters alike.

For those who appreciate outdoor activities, the nearby vineyards and farms offer opportunities for wine tasting and farm-to-table dining experiences. Whether you’re biking along scenic routes or enjoying a sunset stroll along the beach, Orient is a place where you can truly connect with nature.

If you’re considering a move to a serene and picturesque community, Orient, NY, beckons with its charm, natural beauty, and rich heritage. Experience the tranquility and warmth of this enchanting hamlet, where every day feels like a vacation.

Newest Listings in Orient

$949,000

2 Beds ⋅ 2 Baths ⋅ 1029495 MLS

Located in the sought-after Orient by the Sea community, this charming ranch is just a short walk from the Association Sound Beach. The .437-acre property includes a spacious fenced backyard with mature specimen trees and three sheds. Interior highlights include an exposed-beam living room ceiling, solid hardwood doors and cabinets, oak and tile floors, a wood-burning stove, and an updated kitchen. Enjoy one floor living in this well-built home.

700 Plum Island Lane, Orient

$8,400,000

6 Beds ⋅ 7 Baths ⋅ 964447 MLS

Rare opportunity to own a uniquely private 7.49-acre bay front estate in Orient Village. This exceptional waterfront property features a spacious 5700 sq ft main residence with 6 bedrooms, 7 baths, three wood burning fireplaces, three bay garage, expansive front and rear covered porches and panoramic bay views. The 20 x 44 heated pool is complemented with a 860 sq ft pool house featuring open common area, kitchenette, full bath, laundry, two changing rooms, outdoor shower, & porch – creating an ideal setting for entertaining and summer living. A fully fenced clay 60 x 120 ft tennis court is expertly sited, so sun glare is never an issue. The property offers an additional free-standing two-bay garage with second floor bonus space providing flexible options for recreation, boat/bike storage or studio space. The 195 ft wide private walkout bay beach offers sweeping Harbor views of Long Beach State Park, Bug Light House and Orient Yacht Club. The property is ideally located within walking or biking distance to the Village of Orient, Orient Yacht Club, local marinas, Post Office, the Country Store, Oysterponds Historical Society and all village amenities.

1600 King Street, Orient

$6,000,000

3 Beds ⋅ 3 Baths ⋅ 1015950 MLS

Set on 9.1 remarkably private acres in one of Orient's most scenic and protected landscapes, this distinctive residence offers a rare combination of architectural character, beautifully developed grounds, and sweeping pastoral views across meadows, Hallock Bay, and Gardiners Bay beyond. Originally part of the historic Hallock farm, the property has been thoughtfully cultivated over decades. Specimen trees, extensive landscaping, and a pond create a setting that feels both intentional and deeply connected to the surrounding natural environment. The elevated position captures expansive vistas while preserving a remarkable sense of privacy. The cedar-clad home was designed to maximize natural light and take full advantage of its extraordinary surroundings. Floor-to-ceiling windows frame the landscape, while more than 1,000 square feet of porches and decking create a seamless relationship between indoor and outdoor living. Classical proportions are balanced by a contemporary coastal sensibility, resulting in a residence that feels timeless, comfortable, and distinctly North Fork. Outdoor amenities are equally compelling. A large gunite pool is set within a bluestone surround and complemented by a brick patio and pergola-covered terrace. The accessory building immediately adjacent incorporates a pool house, substantial loft space, and a two-car garage, providing flexibility for storage, recreation, or studio use. Located within the coveted Narrow River corridor, the property offers easy access to quiet beaches, exceptional wildlife viewing, and the marina, while remaining moments from Orient Village. Properties of this scale and setting rarely come to market, particularly in a location where protected landscapes and enduring views define long-term value.

4725 Orchard Street, Orient

$2,100,000

1019090 MLS

Build your North Fork Sanctuary on the Sound. This is your opportunity to bypass years of time in the application process. Trustees approval already in place allowing a magnificent 2 story Custom Built home with expansive decks and outdoor spaces and a waterside pool overlooking the Sound. A low bluff with just enough elevation and natural steps to the beach located in a cove allows protection and privacy. Just imagine yourself enjoying the quiet days taking in this spectacular view in the home you have always envisioned escaping to on the North Fork. Floor Plans and Site plan available. Contact Agent

75 Pettys Drive, Orient

$4,250,000

4 Beds ⋅ 5 Baths ⋅ 1007919 MLS

Orient, North Fork - For buyers ready to trade city noise for salt air, open sky, and space to truly exhale, 1640 Grand View Drive in Orient offers the kind of North Fork escape that feels both elevated and completely livable. Set above the shoreline with sweeping, cinematic views over Long Island Sound, this Nantucket-inspired coastal estate combines privacy, scale, craftsmanship, and direct waterfront beauty in one rare offering. With approximately 130 feet of private beach and more than 5,000 square feet of upscale, finely crafted living space, the home is designed around what city life often lacks: light, quiet, room to gather, room to work, and a constant connection to nature. From nearly every principal living area, the setting frames wide-open views of water, sky, and shoreline, creating an everyday backdrop that feels more like a retreat than a residence. A spacious covered porch entry opens to a gracious foyer and sets the tone for the home’s relaxed coastal character. The dramatic living room, with soaring vaulted ceilings, clerestory windows, and expansive Sound views, is made for both slow weekends and effortless entertaining. It is the kind of room that can host a holiday dinner, a laid-back summer gathering, or a quiet night in with multiple fireplaces, a record playing, and the water just beyond the glass. The large dining room offers an elegant setting for dinners with friends and family, while the immaculate kitchen with breakfast area overlooks the lush landscape of this private coastal retreat. The open-plan family room, complete with a gas fireplace, flows naturally to the waterside terrace, blurring the line between indoors and out. Morning coffee, golden-hour cocktails, long summer lunches, and late-night conversations all find their place here, with the Sound as the view. The main level includes a thoughtfully designed owner’s suite with fireplace, sunroom/sitting room, and serene private spaces that make the most of the home’s waterfront orientation. A dedicated home office with private en suite bath adds the flexibility modern buyers want, whether used as a true work-from-home setup, creative studio, guest suite, or potentially a fifth bedroom. Upstairs, the home continues to offer room for everyone and everything: a large sitting room, billiard/family room, sewing or craft room, junior owner’s suite with full bath, and two additional bedrooms connected by a Jack-and-Jill bath. The layout is ideal for hosting weekend guests, extended family, or friends escaping the city for beach days, dinners outside, and slower mornings. Immaculate and exceptionally well-maintained, the estate includes a wine cellar, full-house generator, outdoor shower, and many quality details throughout. The grounds also offer room for a potential waterside pool (permits required), adding the possibility of creating a full resort-style experience at home. For city-area buyers looking for a more grounded way to live without sacrificing style, comfort, or design, 1640 Grand View Drive offers a rare balance: sophisticated coastal architecture, true privacy, direct beach access, and the natural beauty of the North Fork. It is a place to host, recharge, work remotely, spend summers, or simply step into a quieter rhythm of life.

1640 Grandview Drive, Orient

$1,100,000

1006014 MLS

Beautiful .6 acre, waterview building lot on Willow Terrace in Orient. Deeded bay beach a few doors down. Walking distance to Orient village and Yacht Club. Close to sound beaches and North Fork amenities. Design plans in place for a 4 bed, 4.5 bath cedar shingled home. Septic design complete and Health Department permits in process.

1115 Willow Terrace Lane, Orient

$699,000

998459 MLS

Level .919-acre lot in Hillcrest Estates, Orient, NY. Beautiful site with electric and natural gas in the street. Close to Orient State Park, Orient Village, Truman’s Beach, Sound and Bay Beaches. A short drive to Greenport Village for shopping and restaurants.

405 Hillcrest Drive, Orient

$1,625,000

4 Beds ⋅ 3 Baths ⋅ 999463 MLS

Orient Village- located on a quiet street in the coveted coastal village of Orient, this beautifully maintained 4-bedroom, 2.5-bath home borders preserved land, offering exceptional privacy and a serene natural setting. A welcoming wide front porch sets the tone before entering the foyer, which opens to a spacious living room with a wood-burning fireplace. The home features a large eat-in kitchen, formal dining room, and a sun-filled sunroom overlooking the backyard and gardens. In addition, the first floor includes a generously sized primary bedroom, an additional guest bedroom, and a full bath, providing convenient main-level living. Upstairs, a large loft area offers flexible space for a home office or family room, along with two additional guest bedrooms, a guest bath, and a bonus room ready for your creative expansion ideas. Additional highlights include gleaming wood floors throughout, a large unfinished basement with abundant storage space, and a two-car garage. Ideally located just moments from the Orient Yacht Club, all village amenities, beaches, and the Jitney, this special property presents a rare opportunity to enjoy relaxed North Fork living in one of the area’s most sought-after communities. This is the very special home you have been waiting for.

1060 Navy Street, Orient

$1,395,000

4 Beds ⋅ 2 Baths ⋅ 995799 MLS

Wake up to the sound of gentle waves and breathtaking sunrises over Gardiner Bay in this charming four-bedroom, two bath coastal retreat. Nestled in the heart of Orient, this home blends classic North Fork charm with modern comforts. Step inside to find a bright, airy interior with open-concept living spaces, hardwood floors, and windows that capture stunning water views. The spacious kitchen offers ample counter space and flows seamlessly into the dining and living room areas, perfect for entertaining. Outside, enjoy a private porch overlooking the bay and a short stroll to a private sandy beach and Orient’s quaint village. Whether as a year-round residence, weekend escape or investment property, this gem offers the best of the North Fork.

295 Willow Terrace Lane, Orient

$2,375,000

987619 MLS

Rare 17.4-Acre Estate in Orient, NY With a 2.5 Acre & 3 acre single and separate residential building lots separated by 11.9 acres of development rights sold land. This exceptional property offers a unique opportunity to own a versatile, three-part estate in the coveted hamlet of Orient, NY, boasting approximately 20,209 square feet of interior space across multiple structures. Situated in a picturesque North Fork setting, the estate perfectly blends agricultural functionality, equestrian potential, and two opportunities to build a new residence on the 3 acre parcel and/or build a new residence on the 2.5 acre lot or convert an existing 4,578 sq. ft. barn to a residence, with existing architectural plans. Parcel 1 (2.5 Acres – Residential Use) The property's entrance on the main road leads into a thoughtfully arranged 2.5-acre parcel featuring four distinctive buildings. This parcel is also setback form the Main Road by approximately 250 feet. • 1,485 sq. ft. Storage Building: • 4,578 sq. ft. Multi-Use Building: Recently renovated, featuring new Anderson doors and windows, framed interior ready for customization, and a spacious second-floor loft spanning the building’s full width with architectural plans in place to convert to a residence I• 5,015 sq. ft. Concrete Block Storage Building: Impressively designed with 25-foot cathedral ceilings, metal shelving, and a durable concrete slab floor for heavy-duty storage. • A Quaint Cottage Storage Building Parcel 2 (11.9 Acres – Development Rights Sold) Dedicated to equestrian excellence, this fully fenced and tree-lined 11.9-acre area includes: • 6,615 sq. ft. Former Indoor Riding Arena: With expansive 30-foot ceilings, suitable for equestrian training or adaptable for various agricultural uses. • 5,015 sq. ft. Stable Facility: Professionally designed with 20 spacious horse stalls. • Four Paddocks and Riding Area: Enhancing the property’s equestrian appeal with ample space for grazing, riding, and training horses. Parcel 3 (3 Acres – Residential Building Lot) Elevated above the property, this picturesque 3-acre residential lot offers panoramic views over the equestrian estate and stunning vistas of the Long Island Sound. The perfect canvas for a home or a private estate compound. The property is located less than a mile from Narrow River Marina, a perfect destination to keep a powerboat or a sailboat. In addition, there is access to Hallock Bay and Hallock Bay Beach. Additional Features & Potential Uses Electricity services each building, supplemented by generators to ensure uninterrupted lighting and water supply. Beyond equestrian pursuits, this property's potential spans broadly across agricultural uses—including vineyards, cattle farming, organic produce, or other livestock operations. The expansive layout ensures flexibility to match your vision and lifestyle. This Orient property is truly a rare find, combining extensive acreage, practical infrastructure, stunning views, and unlimited possibilities. A prestigious offering on the North Fork—ready to become your ideal agricultural and multi-residential sanctuary.

29525 Main, Orient

$2,850,000

3 Beds ⋅ 3 Baths ⋅ 972026 MLS

Nestled on a private 4-acre land, subdivided in 3 different lots (1,33 acres lot - 0,67 acres - 2 acres lot) with development rights intact, this attractive, 3 bedrooms, 3 bathrooms 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. Photos may include virtual staging and/or digital enhancements. Furnishings and décor shown are for illustrative purposes only. This is a co-listing with Susan Grella and Adrienne Wender of Nest Seekers International.

35335 Main Road, Orient

$2,499,999

5 Beds ⋅ 4 Baths ⋅ 828203 MLS

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 Road, Orient

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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.