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$2,249,000
4 Beds ⋅ 4 Baths ⋅ 1032350 MLS
Welcome to this exceptional estate, just a short walk from a private deeded beach and dock. Designed for entertaining, this spacious property features an impressive outdoor living area complete with a covered, built-in bar and kitchen—perfect for hosting family and friends. Enjoy the quiet, peaceful surroundings while still being close to everything you need. With low taxes and move-in-ready condition, this home offers the ideal combination of comfort and convenience. Furniture is negotiable, and the property may be sold furnished.

705 Gus Drive, East Marion
$1,785,000
4 Beds ⋅ 3 Baths ⋅ 1027434 MLS
Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings, an elegant open staircase, and an inviting sense of scale that sets the tone for the home's thoughtfully designed interior. The main level offers an exceptional layout for both everyday living and entertaining, featuring a formal dining room, gracious living room, and an inviting media room anchored by a classic wood-burning fireplace. At the heart of the home, the spacious eat-in kitchen is appointed with abundant cabinetry, generous counter space, and a highly functional layout designed to accommodate everything from casual everyday meals to large-scale gatherings. Just beyond, a private home office overlooks the rear grounds, providing a peaceful and inspiring workspace. Occupying nearly 900 square feet, the second-floor primary suite serves as a true private retreat, complete with dual custom walk-in closets and a luxurious spa-inspired bath featuring double vanities, a walk-in shower, and a Jacuzzi soaking tub. Three additional guest bedrooms and a well-appointed full hallway bathroom complete the upper level, providing comfortable accommodations for family and guests alike. Another huge bonus is the expansive unfinished basement with 8' ceilings and walk-out egress already in place, making this ripe for another fully finished space which would add approximately 1400 additional sqft. Perfectly positioned within one of Greenport's most desirable beach communities, residents enjoy private access to the Rock Cove Estates association beach while remaining just minutes from the vibrant shops, acclaimed restaurants, marinas, and waterfront attractions of Greenport Village, as well as the renowned wineries, farm stands, and scenic beauty that define the North Fork lifestyle.

90 Caiola Court, Greenport
$1,299,000
4 Beds ⋅ 2 Baths ⋅ 1021286 MLS
This storybook circa 1858 cottage captures the very essence of North Fork living: cozy, charming, and effortlessly inviting. Rich in history and timeless appeal, this beautifully preserved home blends the simplicity of a bygone era with thoughtful modern updates, creating a warm and welcoming retreat. Inside, random-width wide plank flooring adds authentic character throughout. The first floor offers a spacious primary bedroom, a second bedroom or home office, an inviting living room, formal dining room, and an eat-in kitchen with a convenient laundry area. Upstairs, two additional bedrooms and a half bath provide comfortable accommodations. Architectural details enhance the home's enduring charm, from the welcoming semi-wraparound covered front porch to the side deck with a new retractable awning overlooking beautifully landscaped gardens. A pergola with a slate patio creates the perfect setting for outdoor dining, entertaining, or simply relaxing on a summer evening. Adding to the property's appeal is a detached 2-car garage and a delightful artist's or hobby studio, complete with its own pergola-covered sitting area nestled among lush gardens. Privately tucked behind a classic white picket fence, the beautifully landscaped .5-acre property is an exceptional outdoor sanctuary. The backyard features a heated free-form Gunite pool with a cascading waterfall, a pool shed with deck, two additional storage sheds, mature trees, and an abundance of seasonal flowering plantings, creating a peaceful and private oasis. Ideally located just minutes from pristine beaches, golf courses, marinas, renowned wineries and breweries, county parks, farm stands, Hampton Jitney and popular local eateries. This special property also enjoys close proximity to Historic Greenport, where waterfront dining, boutique shopping, and galleries await. The backyard abuts a nature preserve that leads to Marion Lake County Park. Nothing can be built behind it. Whether you're enjoying a quiet morning coffee on the porch, spending the afternoon poolside, or entertaining friends after a day at the beach, this one-of-a-kind North Fork treasure offers the perfect blend of historic character, modern comfort, and relaxed coastal living.

8440 Main Road, East Marion
$1,899,999
1017889 MLS
Very near the eastern tip of Long Island’s renowned North Fork, this exceptional 1.37-acre beachfront property presents one of the few remaining opportunities to create a legacy waterfront estate in one of Orient’s most breathtaking coastal settings. Surrounded by panoramic views of Gardiners Bay, Long Island Sound, Plum Island, and the Connecticut shoreline, this remarkable homesite enjoys direct access to a sandy beach and the added distinction of neighboring protected Suffolk County parkland, preserving the natural beauty and open coastal landscape that define this extraordinary location. With approximately 125 feet of private beachfront, the property offers an ideal setting for relaxed coastal living and entertaining. The grounds provide ample space for hosting weekend guests, extended family, or friends escaping the city for beach days, outdoor dining, and slow, restorative mornings by the water. There is also the potential for a waterside pool (permits required), creating the opportunity to design a true resort-style coastal retreat. Wake to spectacular sunrises over Long Island Sound and embrace the quintessential North Fork lifestyle. Spend your days boating, kayaking, paddleboarding, fishing, swimming, beachcombing, or exploring the scenic trails and shoreline of nearby Orient Point County Park. Walk along the beach to take in views of the iconic Orient Point Lighthouse, affectionately known as the “Coffee Pot,” or take the nearby Cross Sound Ferry to New London for a day trip before returning home to the peace and privacy of your waterfront escape. Just minutes away, enjoy the charm of Orient Village, award-winning North Fork vineyards, local farm stands, marinas, and the iconic Duryea’s, where waterfront lunches and unforgettable sunset dinners are part of everyday life. For buyers seeking a more grounded way of living without sacrificing style, comfort, or design, this property offers a rare balance of sophistication, privacy, and direct beachfront access. It is a place to host, recharge, work remotely, spend summers, or simply step into a quieter rhythm of life. For city-area buyers ready to trade noise for salt air, open sky, and space to truly exhale, 1890 Lands End Road offers a rare North Fork escape that feels both elevated and effortlessly livable, where cinematic water views, natural beauty, and true coastal privacy come together in one extraordinary offering.

1890 Lands End Road, Orient Point
$1,377,000
3 Beds ⋅ 3 Baths ⋅ 998976 MLS
Okay, so the first thing, you get out of the car and this farmhouse style has the front porch that actually has room for a side table and chair to have my morning coffee in peace that I have wanted so badly. Then inside, the half bath is right next to the front door, but it's tucked far enough away from the open living room and kitchen that it doesn't feel awkward when all of us are hanging out. The kitchen has the paneled fridge, a real pantry closet and open shelves that I have always liked. The kitchen sink is setup where I am staring out to the backyard when I am stuck doing dishes, so good. They even say there is room for a pool. Then the dining room has this full glass slider to the yard, so the whole back of the house is just filled with light, you can even see the view of the yard from the living room. Upstairs, the ensuite bathroom is honestly my favorite surprise, the floor is so interesting, and the whole space feels calm with the finishes they picked. Even the downstairs bathroom has this beautiful wallpaper that makes this new construction feel intentional, not an afterthought. What I love is this location makes you feel like you found a secret corner of Greenport. You're literally tucked up against the maple tree forest, so it's quiet and green in the best way. The backyard is fully fenced so if the decision is for the pool, it doesn't feel tight. They are putting in a stone patio for outdoor dining table and seating to bring the backyard views together. What a great idea. And because this one is New Construction, everything just feels solid and reliable. Best part, the house is also a half mile away from the LIRR train station and Hampton Jitney stop to get to NYC, then Aldo's coffee shop is a 3 minute bike ride or 10 minute walk. I think this might be the one, you have to come see it.

550 Madison Avenue, Greenport
$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
$1,300,000
3 Beds ⋅ 3 Baths ⋅ 982221 MLS
This ranch style home offers a blend of comfort, convenience, and opportunity. With three spacious bedrooms and three beautifully finished bathrooms, the home provides generous space for relaxation, work, or entertaining. The well-appointed kitchen features a stainless-steel appliance package, Quartz countertops, and a Thor range and hood, combining style with functionality. The homes’ living room with wood-burning fireplace, creates a warm and welcoming atmosphere throughout the seasons, while the enclosed sunroom fills the home with natural light and is the perfect setting for year-round enjoyment. Set on a generous .63 acre lot, the property also offers a detached garage that adds valuable storage and workspace as well as ample room for a pool. Located in the vibrant community of East Marion, this home is in close proximity to local eateries, parks, beaches and other recreational amenities. Do not miss the chance to explore all the possibilities this special property has to offer.

10940 Main Road, East Marion
$1,350,000
3 Beds ⋅ 2 Baths ⋅ 966420 MLS
This classic Greenport Village Craftsman has the kind of charm that is getting harder to find — bright, airy rooms, beautiful period detail, and an easy coastal feel just one block from the beach. Front and back porches provide multiple outdoor seating areas. Inside, the home features coffered ceilings, warm wood floors, and sun-filled living and dining spaces. Outside, the private, fully fenced backyard is well suited for summer living, w/wisteria-covered arbor for dining & entertaining. room for a pool. the detached garage with outdoor shower could work well as a pool house, studio, or additional entertaining space. This special property is close to a sandy Bay beach, the LIRR, SI Ferry, restaurants and the lively Village downtown. Perfectly located to explore the vineyards, farm stands, fishing spots and all that the North Fork offers.

210 5th Street, Greenport
$1,529,000
4 Beds ⋅ 3 Baths ⋅ 961091 MLS
Experience the beauty of coastal living with this young Colonial built in 2006 and set on 1.2 verdant level acres of privacy and seclusion. The expansive front yard, complemented by a grand circular driveway, creates a lasting first impression. The welcoming covered front porch is perfect for sipping your morning coffee while the equally expansive rear yard is ideal for star gazing on warm summer evenings or hosting large gatherings. An open floor plan connects the living, dining and kitchen spaces offering seamless daily living and makes entertaining a breeze. Four generously-sized bedrooms including a substantial primary ensuite with jacuzzi and an additional hall bath, complete the second floor. There is unfinished attic space above the attached two-car garage and a full unfinished lower level with high ceilings which may provide a blank slate for even more living space. Located just down the road from renowned Rocky Point Rd. Beach, a fresh vegetable stand and fragrant lavender farm, this home is also just a stone's throw from convenient ferries, a myriad of wineries and acclaimed Greenport with world class dining. This gem offers a fantastic opportunity to enjoy all the North Fork is so well known for and more!

2655 Rocky Point Road, East Marion
$2,195,000
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
$2,100,000
5 Beds ⋅ 5 Baths ⋅ L3579812 MLS
This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed and Breakfast (formerly Rubys Cove) with front and back staircases, large parlor rooms and an updated kitchen. Bay Avenue is an amazing location just steps to Main and Front Street shops, fine restaurants, and all transportation., Additional information: Appearance:Excellent,Interior Features:Lr/Dr,Separate Hotwater Heater:y

151 Bay Avenue, Greenport

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.