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$1,459,000
3 Beds 2 Baths 983029 MLS
Water view meticulously renovated 3 bedroom 2-bath corner home in Greenport, offering privacy with a landscaped fenced-in garden. A true sanctuary, a large side open spacious garden with mature trees and an intimate private patio that overlooks the picturesque Sterling Harbor, alive with sailboats and fishing vessels. This thoughtfully renovated home has been thoroughly rebuilt, showcasing its architectural charm including pine flooring and a classic front porch. The lower level boasts an open-concept kitchen and living area, complemented by a sun-drenched room with water views, separated by pocket doors, ideal for a formal dining room or a versatile third bedroom. A full bath on this level adds convenience. Upstairs, you'll find two comfortable bedrooms and a dedicated small office area, all overlooking the serene rear garden and harbor. A second full bath completes the upper floor. There is also a full attic and a separate one car garage that is ideal for a possible future accessory housing unit and/or a great workshop equipped with its own 100 amp electric service. A pool or a rear extension are both possible options for a future owner. An Easy walk to the Greenport Village, or 15 minute walk to the Peconic Bay Manhasset Beach or to the LI Sound 67 steps Beach.

412 Atlantic Avenue, Greenport

$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

$859,900
3 Beds 2 Baths 960613 MLS
PRICE IMPROVEMENT!! Whether year-round living or a summer getaway, do not let this one "Get Away"! Located on the much-desired Gull Pond Lane, this classic ranch-style home presents a rare opportunity to create your North Fork Dream. Architectural design plans for renovation are available to view. This home features freshly refinished hardwood floors, 3 bedrooms, 1 newly updated full bath, one primary suite half bath, a formal dining room, a spacious and inviting living room with a wood burning fireplace, large picture window and custom built-ins, a whole house standby generator and a full basement with endless possibilities. Updates also include Hot Water Tank, CAC, Electrical Service and most windows. Set on a generous-sized private lot, it is the perfect setting for quiet times or outdoor entertaining. Conveniently located, this hidden gem is near Greenport Village shops, award-winning restaurants and wineries, marinas, farm stands, Island's End Golf & Country Club, Shelter Island Ferry and beaches. This fabulous home is being sold as-is. Make it the sanctuary where your history continues.

290 Gull Pond Lane, Greenport

$4,250,000
3 Beds 2 Baths 923793 MLS
Exceptional soundfront offering combining a beautifully maintained waterfront residence with a rare, separately buildable adjacent lot—creating a unique opportunity for legacy ownership or future development. The existing home sits on .75 acres with direct, no-bluff access to the Sound and showcases sweeping 180-degree panoramic water views. This 3-bedroom, 2-bath residence features a waterside gunite pool and an open-concept interior with modern finishes, designed for effortless indoor-outdoor living and year-round enjoyment. Expansive windows fill the home with natural light while capturing stunning sunsets over the water. Included in the offering is an additional .80-acre unimproved soundfront parcel, providing exceptional flexibility—whether to create a multi-generational compound, expand the existing footprint, or develop a second residence for investment or resale. Ideally located in Greenport near beaches, shops, and acclaimed dining, this rare dual-parcel property delivers a compelling blend of coastal lifestyle, privacy, and long-term value.

56875 Route 48, Greenport

$2,650,000
3 Beds 2 Baths 975674 MLS
Beautiful, expansive soundfront retreat offering rare, direct waterfront access with no bluff and sweeping 180-degree panoramic views. Set on .75 acres, this exceptional 3-bedroom, 2-bath home features a waterside gunite pool perfectly positioned to capture breathtaking sunsets over the Sound. The interior showcases modern finishes and an open-concept layout designed for effortless indoor-outdoor living, ideal for both relaxed summer getaways and comfortable year-round living. Large windows flood the home with natural light while framing the stunning water views throughout. Ideally located in Greenport, just moments from pristine beaches, charming shops, and renowned restaurants, this meticulously maintained property delivers a seamless blend of privacy, convenience, and coastal elegance.

56765 Route 48, Greenport

$1,950,000
4 Beds 3 Baths 970247 MLS
Built in 2021 and offered in like-new condition, this stylish four-bedroom residence pairs clean contemporary design with the relaxed ease of North Fork living. A semi-open floor plan creates natural flow across the main level, connecting the living, dining, and kitchen spaces in a layout equally suited for everyday living and effortless entertaining. Four spacious bedrooms offer comfortable accommodations, while a full unfinished basement presents excellent potential for additional living space, whether for a media room, gym, recreation area, or some combination. The primary bedroom enjoys vaulted ceilings, plenty of natural light and a generous ensuite bath. Outside, a heated saltwater pool is set within mature, thoughtfully designed landscaping that provides both privacy and a beautifully established backdrop for summer days. Deeded HOA access to a pristine Sound beach, Eastern Shores, completes this exceptional offering. Located less than a mile from the heart of Greenport Village, home to coveted restaurants, boutique shops, coffee shops, and marinas.

660 Sutton Place, Greenport

$3,195,000
6 Beds 6 Baths 971817 MLS
UNDER CONSTRUCTION - IN PHASE 1 - PROPERTY IS CURRENTLY BEING CLEARED FOR EXCAVATION - Discover an exceptional new construction in the beloved Pebble Beach Farms of East Marion. This stunning modern farmhouse build is thoughtfully designed with an open living space through generous quarters encompassing six bedrooms, five and half bathrooms and dedicated entertaining space inside and out. The design incorporates sought out features such as first floor bedroom with ensuite bath, large double shower with soaking tub in the master bedroom, a rear balcony off of the master bedroom overlooking the rear preserve and covered rear patio. A bright open concept layout highlights a chef’s kitchen with island, pantry and high end appliances with additional amenities including natural hardwood throughout, central air, smart thermostat technology, a finished walk out basement and detached one car garage across 4,175 sqft of interior living space. Outside, enjoy a lush landscaped yard with in ground vinyl heated pool backing the communities preserved land for plenty of privacy and tranquility. Pebble Beach Farms offers exclusive access to its own private beach, tennis courts, basketball, bocce ball and pickle ball in its own community park. In close proximity is the famed Kontokosta Vineyard, Islands End Golf Club and seconds from Greenport Village. East Marion is one of the North Fork’s best-kept secrets offering privacy, charm, and easy access to everything you love about the Northfork. Claim your Northfork getaway now for opportunities to still customize finishes, features, textiles and colors.

345 The Strand, 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

$2,400,000
4 Beds 2 Baths 945943 MLS
Modern Log Home Retreat with Deeded Water Access & ADU Potential | Greenport, NY Discover a truly distinctive single-family modern log home set within one of Greenport’s most coveted peninsula locations. Built in 2003 and thoughtfully renovated in 2021, this 2,396 sq. ft. residence offers 4 bedrooms, 2 baths, and 9 well-proportioned rooms designed for comfort, privacy, and effortless indoor outdoor living. Soaring, classic log home ceilings anchor the interiors, creating a dramatic yet warm atmosphere throughout. The main living spaces flow seamlessly to a sprawling, fully furnished deck—ideal for entertaining or unwinding in complete tranquility. A newly installed saltwater, heated in-ground pool (2025) and a 7-person hot tub elevate the property into a private resort-like setting. Stainless steel appliances, added during the 2021 renovation, have seen minimal use and remain in excellent condition. All Certificates of Occupancy for interior and exterior work have been recently updated (2024/25). Set on 3.88 serene acres and partially surrounded by over 30+acres of protected land and nature preserve, the property offers a rare sense of seclusion while remaining close to the best of the North Fork lifestyle. Enjoy a woodland retreat atmosphere paired with direct water access—including a deeded right of-way and dock rights to a shared deep-water floating dock just across the street on highly desirable Gull Pond. The dock can accommodate vessels approximately 30+ feet, offering the pleasure of dock access without the concerns of flood risk or the need for FEMA flood insurance for the main property. Adding exceptional flexibility, the property includes a 1,000 sq. ft. accessory building, ready for potential ADU transformation (subject to appropriate approvals), creating an opportunity for a true private compound, guest quarters, or additional living space. The location is equally compelling: walk to local favorites such as Portabello of Sterling Harbor, Billy’s on the Bay tiki-style eatery, Islands End Public Golf Course, and Sterling Harbor marinas. A quick bike ride brings you to the maritime village of Greenport, tranquil beaches, and all the charm the area is known for. Documented seasonal rental potential further enhances the property’s appeal. Property Highlights * 4 Bedrooms | 2 Baths | 2,396 Sq. Ft. * 3.88 Acres * Built 2003 | Renovated 2021 * Modern log home with tall, classic ceilings * New heated saltwater pool (2025) + 7-person hot tub * 1,000 sq. ft. accessory building with ADU potential * Deeded water access & dock rights with boat slip * No FEMA flood insurance required * Sold with all contents, if desired * Tax Map: 1000-035-00-03-00-012-001 This is a rare opportunity to own a private North Fork retreat that balances nature, water access, and proximity to Greenport’s vibrant lifestyle. Property can be sold with all contents ready for use if needed.

1710 Gull Pond Lane, Greenport

$1,249,000
4 Beds 2 Baths 940213 MLS
* low-maintenance North Fork lifestyle, * weekend retreat, * turnkey without renovation headaches, * walkability, * lock-and-leave second home, * income potential, * simpler ownership vs larger estates “Freshly repositioned for the spring market, this beautifully renovated Village home offers exceptional value and immediate enjoyment. Featuring a complete renovation including new roof, siding, HVAC, appliances, and hardwood flooring throughout. The property also offers potential for additional living space—please discuss possibilities . Seller welcomes serious inquiries and will consider all reasonable offers .This home is ideally located just minutes from the heart of Greenport Village, offering access to the harbor, Mitchell Park, mass transportation and the waterfront, shops, restaurants, cafes, galleries, and the LIRR station, making this a convenient locations in the village. The property sits close to marinas, beaches, and ferry service to Shelter Island, and is close to the North Fork’s vineyards and farm stands. This location provides the perfect blend of quiet residential living” with all of Greenport’s amenities just minutes close. All information provided should be verified by the buyer, all information including but not limited to taxes, location, permits, square footage, should be verified by buyers. Equal housing opportunity

336 2ND Street, Greenport

$1,499,000
4 Beds 2 Baths 934356 MLS
Scenic and bucolic, this 3+ acre country farm is steeped in classic North Fork charm. The property features an authentic 1800s four-bedroom, one and a half bath, farmhouse, a 2+ car garage (1976) with a workshop, office and mechanics pit, and a 1985 barn equipped with three horse stalls and ample space for tractors. Additional structures include a cinderblock chicken coop and a pig sty, offering true farmstead character. A large, established two thirds of an acre vegetable garden and an active farm stand highlight the property’s agricultural potential, while the watering hole rises and falls with the rains. This less than one-mile pastoral Greenport lane has over 130 acres of preserve land with another 50 plus acres of land on this lane soon to be preserved. Whether you choose to reimagine, repurpose, or simply enjoy this unique homestead as it is, the possibilities are abundant. A memorable bay beach just under one mile away. Please do not walk the grounds unattended.

1760 Albertson Lane, Greenport

$1,250,000
4 Beds 3 Baths 922473 MLS
Greenport - Historic Colonial Farmhouse in Peconic Bay Estates. Offered for the first time in decades is this rare slice of Long Island history. Step back in time without sacrificing modern comfort in this circa 1600s, Dutch Colonial farmhouse, gracefully set on .39 acres in the heart of the North Fork. With 4-5 bedrooms, 3 full baths, and over 400 years of character, this one-of-a-kind home blends heritage and warmth with beachy, coastal charm. Features include original wide-plank floors, five wood-burning fireplaces, a charming eat-in country kitchen, a spacious dining room & inviting living room, walk-in pantry, and an oversized laundry room with antique tub. Deeded beach access is just steps away. Enjoy the best of both worlds: secluded & serene, yet very close to historic Greenport Village, home to the iconic carousel, North Fork Arts Center at the Greenport Theatre, and artisanal shops. Explore the nearby charm of historic Southold Town, and spend weekends sampling world-class restaurants, seafood markets, vineyards, craft breweries, and farm stands. Live music & local culture make this a perfect year-round residence or getaway. Your North Fork dream awaits! Steeped in history, and surrounded by beauty.

240 August Lane, Greenport

$1,149,900
3 Beds 2 Baths 921412 MLS
Welcome to this beautifully appointed single-family residence ideally situated just minutes from the charming village of Greenport. Blending modern amenities with classic coastal charm, this property offers not only an exceptional retreat in one of Long Island’s most sought-after locations—but also a compelling opportunity as a fully functional or potential income-producing short-term rental. Whether you’re seeking a weekend escape, a second home that offsets its own costs, or a turnkey investment in the thriving North Fork vacation market, this home delivers versatility and value. INTERIOR FEATURES: The home showcases a thoughtfully designed open-concept layout. The gourmet kitchen features white cabinetry, granite countertops, subway tile backsplash, and premium stainless steel appliances. The spacious living area is anchored by a cozy fireplace, while hardwood floors flow throughout. Multiple bedrooms offer comfort and privacy, complemented by updated bathrooms featuring glass-enclosed showers, stone tile walls, and granite countertops—ideal for both personal use and guest accommodations. OUTDOOR LIVING: Set on over half an acre, the expansive property is designed for relaxation and entertainment. A stunning rectangular swimming pool, stone-paved deck, and extensive patio space create a resort-like atmosphere highly desirable for short-term guests and homeowners alike. Mature landscaping and privacy fencing provide a serene and secluded outdoor setting. ADDITIONAL AMENITIES: Unfinished basement offering excellent potential for recreation space or added value Dedicated laundry room Ceiling fans throughout Attached garage with paved parking INCOME & INVESTMENT POTENTIAL: Located in one of the North Fork’s most in-demand vacation destinations, this property is well-positioned for short-term rental use. With strong seasonal demand driven by wineries, beaches, and year-round tourism, buyers have the opportunity to generate income while enjoying personal use. Ideal for those looking to own a lifestyle property that can also serve as a revenue-generating asset. LOCATION & LIFESTYLE: Just a short drive from historic Greenport Village, this home offers easy access to boutique shopping, acclaimed restaurants, and waterfront activities. Enjoy proximity to award-winning wineries, pristine beaches, marinas, and a vibrant calendar of community events including the Maritime Festival and Winter Wonderland. The North Fork’s renowned farm-to-table dining, farmers markets, art galleries, and cultural venues are all within reach, along with convenient access to the Hampton Jitney and LIRR. This property offers more than just a home—it’s an opportunity to experience the best of the North Fork lifestyle while capitalizing on one of the region’s most desirable and in-demand markets. Whether for personal enjoyment, investment, or both, this is a rare offering in Greenport.

380 Homestead Way, Greenport

$2,150,000
4 Beds 4 Baths 915982 MLS
This beautifully renovated 4 bedroom + den and office waterfront home (house is not in a flood zone) offers a seamless blend of modern comfort and timeless coastal style. Walkable to the village, beach, restaurants and jitney pick up! Inside, the expanded floor plan opens into spacious, light-filled living areas designed for both everyday living and entertaining. A first-floor ensuite bedroom adds convenience and flexibility. High ceilings and expansive windows frame the water views, filling the space with natural light. The custom chef’s kitchen features top-of-the-line appliances and flows easily into both formal and informal dining areas. The large living room includes a gas fireplace, game area, and a striking marine-lacquered wet bar complete with fridge/freezer adjacent to both pool and living areas. An additional den with water views offers a quiet retreat or extra space for guests. Outdoors, cedar fencing encloses a private backyard with a heated saltwater pool, areas for al fresco dining, and space to relax. Upstairs features two guest bedrooms sharing a well-appointed designer bath, tub shower combo. The primary suite has stunning water views, cathedral-ceiling, a separate sitting room/office, spacious dressing room, and a spa-like bath with soaking tub, large shower, and separate water closet with bidet. Stone steps lead through beach grass to a private dock—perfect for boating, kayaking, or paddle boarding. Located a few blocks outside Greenport village, yet tucked away from the crowds, and near one of the North Fork’s best bay beaches, this home offers the ideal balance of serenity and convenience. Also available furnished.

980 Manhanset Avenue, Greenport

$1,695,000
4 Beds 4 Baths 909423 MLS
Modern Design Meets Coastal Living Welcome to your brand-new custom build in East Marion-crafted with an eye for detail and built for everyday luxury. This 4-bedroom, 3.5-bath home, complete with a spacious primary en-suite, balances timeless design with modern conveniences in a coveted beach community. Step inside to soaring ceilings, red oak select flooring, and Allwood custom cabinetry anchored by sleek quartz countertops. The kitchen is a chef's dream, featuring a Galiano Moena 36" gas range, double electric wall ovens, and a 24" wine cooler-because hey, why not! Light-filled spaces flow seamlessly to the outdoors, where a custom 18x36 Gunite saltwater pool (heated, of course) promises endless summers. Porcelain stone pavers and a generous patio set the stage for entertaining or unwinding after a swim. Additional highlights include cedar shake siding with a metal and asphalt roof, and a fully finished basement offering flexible space for media, fitness, or guests. It's not just a house-it's a backdrop for life at the beach. The right blend of craftsmanship, convenience, and coastal attitude. Could be you!

1900 Gillette Drive, East Marion

$749,999
5 Beds 4 Baths 898986 MLS
"Live Where Others Vacation" paired with "Approx. 2,800 Sq. Ft. of Finished Living Space" and "Minutes to LIRR". An exceptional opportunity to own in the highly sought-after Greenport / North Fork region, where lifestyle, flexibility, and long-term value come together. Whether you are seeking a "weekend getaway", "investment", "one of the North Fork's most desirable destinations", "year-round residence", "weekend retreat", "possibilities are endless", this well-maintained ranch offers outstanding versatility in one of Long Island’s most desirable coastal destinations. Welcome to 395 Linnet Street, also known as 806 Linnet Street. Designed for today’s casual lifestyle, the home features an open-concept layout, 3 bedrooms and 2 full baths, 1,400 square feet on the main level, along with an updated eat-in kitchen showcasing quartz countertops. The expansive backyard creates the perfect setting for entertaining, outdoor dining, or simply enjoying the peaceful North Fork atmosphere. The fully finished lower level [1,400 square feet] with outside entrance (OSE) offers additional bedrooms and baths (all on Certificate of Occupancy), creating exceptional flexibility for extended living, guests, private work-from-home space, recreation, or separate accommodations. Located just minutes from bay beaches, marinas, parks, vineyards, farm stands, acclaimed restaurants, boutique shopping, the historic Greenport waterfront village, LIRR, and Hampton Jitney, this property places you in the center of the North Fork lifestyle that continues to attract homeowners and weekend visitors alike. Minutes to Beaches, Vineyards & Greenport Village

395 Linnet Street, Greenport

$2,599,000
4 Beds 3 Baths 862263 MLS
Soundfront! Welcome to 2100 Sound Drive - offering water views from nearly every room, this unique property is part of the Eastern Sterling Shores community and is truly the Last of the Mohicans! Greeted by a welcoming circular driveway and situated atop a picturesque bluff, you'll enjoy captivating views and summer breezes. Stairs lead to an enchanting enclosed bungalow while your own private oasis awaits beyond and within just 40' of this pristine property are bountiful fish and lobster, ideal for the fishing enthusiast. At the center of this entertainer’s delight is an oversized living room accented with dramatic beamed ceilings, a stone wood-burning fireplace and custom built-ins. Four bedrooms, three full baths as well as an eat-in kitchen, formal dining room, all-season room, huge rear patio and attached 2-car garage, complete this special home. Located just a stone's throw to Greenport Village with fine-dining, shopping and ferry access, don't miss this incredible opportunity! Property sold as is.

2100 Sound Drive, Greenport

$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

$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.