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$1,595,000
6 Beds ⋅ 2 Baths ⋅ 1043177 MLS
Introducing an exceptional opportunity to own a truly turnkey, fully restored farmhouse-style two-family home in a prime Greenport Village location. 430 First Street features two meticulously updated residences, each offering three bedrooms, one full bathroom, and thoughtfully designed living spaces. The upper-level residence encompasses approximately 850 square feet and features soaring vaulted ceilings with decorative cross beams and an open-concept Great Room seamlessly connecting the kitchen, dining, and living areas. Three generously sized bedrooms, a full bathroom, and an in-unit washer and dryer complete the space. The main-level residence offers a similar layout with approximately 870 square feet of living space. Highlights include three bedrooms, one full bathroom, a spacious kitchen with vaulted ceilings, and separated living room, providing added flexibility and room to spread out. Outside, the property is equally impressive, with meticulously maintained landscaping, a newly installed crushed-stone driveway with Belgian block edging, a large rear lawn, full irrigation, and a charming front porch. A substantial 450-square-foot, two-car garage and additional storage shed further enhance the property's functionality. Whether you're an investor seeking a ready-made income-producing property or an end user looking to offset carrying costs with rental income, 430 First Street presents a compelling opportunity in the heart of Greenport Village. Located just two blocks from Greenport's vibrant business district, the property offers convenient access to public transportation, shops, restaurants, grocery stores, local farm stands, parks, and beaches—all while providing the space, condition, and versatility that make this a truly special offering.

430 1st Street, Greenport
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 1040676 MLS
What stands out about this home is how established and inviting it already feels. Mature trees and thoughtful landscaping surround the property, creating a beautiful setting from the moment you arrive. The covered front porch is a perfect place to sit and take in the changing colors of spring and summer, including the striking blue blossoms of the mature Vitex that become a highlight of the landscape each season. Inside, the home has an easy, open flow with wood floors, a spacious hallway leading to the bedrooms, and a living room and kitchen that connect naturally for everyday living and entertaining. Just off the garage, the laundry room and mudroom create a practical drop zone for shoes, bags, beach gear and everything else that helps keep the main living spaces organized. The fenced backyard has its own personality, with an outdoor fire pit, established vegetable gardens, a huge fig tree and an additional garden shed for tools, bikes and outdoor storage. It is the kind of yard that already feels lived in, cared for and ready to enjoy. Location adds another layer to the lifestyle. Iconic 67 Steps Beach is within walking distance for those incredible sunsets over Long Island Sound, while Greenport's coffee shops, restaurants and village destinations are close enough that grabbing your morning coffee does not always have to involve getting in the car. It is a home that combines comfortable everyday living with gardens, outdoor spaces and one of the things that makes Greenport so special: the ability to enjoy the beach, the village and the North Fork lifestyle right outside your door.

435 Sound Road, Greenport
$599,000
2 Beds ⋅ 2 Baths ⋅ 1038348 MLS
Welcome to easy North Fork living in Pheasant Run. This spacious 2-bedroom, 2-bath condominium offers a comfortable single-level layout with vaulted ceilings and abundant natural light. The home features a bright kitchen with ample cabinetry, a dining area with built-in window seating, and a generous living room with direct access to the rear deck and lawn. The primary bedroom includes a private full bath, while a second bedroom and full bath provide flexibility for guests or a home office. A full basement offers substantial storage and additional possibilities. Enjoy central air, a private outdoor space, and the ease of condominium living, all just minutes from Greenport Village, beaches, wineries, restaurants, shopping, and everything the North Fork has to offer.

1235 Calebs Way Unit #G25, Greenport
$1,175,000
4 Beds ⋅ 3 Baths ⋅ 1037504 MLS
Pool, private beach access and the North Fork lifestyle—all in one Greenport property. Set on approximately one-third acre, this spacious Cape offers 4 bedrooms, 2 full baths and approximately 2,400 square feet of above-grade living space, surrounded by mature landscaping and exceptional outdoor amenities. The private backyard is designed for summer living and entertaining, centered around an in-ground swimming pool, expansive outdoor areas and a secluded firepit setting. Just beyond home, enjoy private community beach access (Sterling Eastern Shores)—an increasingly rare amenity and the perfect setting for swimming, relaxing by the water and unforgettable Greenport sunsets. Inside, generous living spaces include a fireplace living room, separate den, open kitchen and dining areas, large bedrooms, first-floor laundry and flexible home-office space. The layout provides room to gather as well as plenty of space to spread out. A substantial finished lower level with separate exterior entrance provides additional flexible-use space, including laundry, a renovated bath and additional finished rooms. An oversized workshop adds even more versatility for hobbies, projects and storage. Whether you’re looking for a year-round North Fork home or a weekend retreat, this home offers a combination that’s difficult to duplicate space, privacy, a swimming pool, private beach access and the Greenport lifestyle.

130 Tasker Lane, Greenport
$629,900
1038007 MLS
Welcome to 400 Aquaview Ave, East Marion, a rare opportunity to create your own North Fork retreat in desirable East Marion. Situated on approximately 0.56 acres, this vacant parcel offers a wonderful setting for those looking to establish a home in one of the East End’s most charming coastal communities. The lot sits around 150ft x 175ft affording ample space for a generous sized home, pool and outdoor entertainment space. The property fronts Aquaview Ave but also extends to Circle Dr W for if creating a nice private drive is in your vision. Surrounded by the natural beauty and relaxed atmosphere that define the North Fork, the property provides an exciting opportunity to bring your dream home to life. Just a short walk away you'll find access to sound beaches at the top of Rocky Point Road, Kontokosta Winery, Greenport Village, Orient Point Ferry and all the beauties of the North Fork.

400 Aquaview Avenue, East Marion
$825,000
3 Beds ⋅ 2 Baths ⋅ 1037952 MLS
Charming Greenport Village Getaway Enjoy the best of the North Fork from this inviting 3-bedroom, 2-bath home, perfectly located near all that Greenport Village has to offer. Stroll to Mitchell Park, waterfront dining, restaurants, shops, and the Shelter Island Ferry, or spend the day exploring nearby vineyards and Greenport Harbor Brewing Company. A wonderful opportunity to enjoy the relaxed charm, walkability, and vibrant lifestyle of Greenport Village—close to everything, yet your own peaceful retreat.

429 Kaplan Avenue, Greenport
$799,000
1 Beds ⋅ 1 Baths ⋅ 1035656 MLS
A rare opportunity to own an early 20th-century Adirondack-style cottage in Greenport, ideally situated just 0.12 miles from a beautiful Sound beach and only one mile from the heart of Greenport Village. This charming cottage showcases many of the home’s original details starting with a screened-in front porch spanning the full width of the facade, creating a welcoming indoor/outdoor retreat. Inside, the open floor plan includes a living/dining room with a wood-burning stove, an eat-in kitchen, full bath, laundry, and access to a rear deck. The second floor offers a cozy loft-style bedroom. Two additional accessory structures, each with electricity and water, provide flexible space for a home office, studio, or creative workspace. Surrounded by trees creating privacy and offering open vineyard views, this distinctive cottage compound captures the relaxed character and timeless appeal of the North Fork.

44 (1180) Sound Road, Greenport
$1,499,000
3 Beds ⋅ 2 Baths ⋅ 1031857 MLS
Experience waterfront living at its finest, in this exceptional cottage located directly on the Bay. This turn-key, one of a kind property, offers gorgeous water views and open concept living. The dramatic vaulted ceilings with exposed beams, create a stunning focal point, adding warmth, texture, and character throughout the living space. Step outside to your own private beach; perfect for swimming, kayaking, paddle boarding, boating, entertaining, or simply relaxing with your feet in the sand. The panoramic views create an unmatched open-bay lifestyle. Wake up each morning to the soothing sounds of the bay and breathtaking sunrises over the water, just steps from your door. This 3 bed 1.5 bath is waiting for you. Located in peaceful East Marion, this home has close proximity to the Jitney, LIRR, amazing restaurants, and the best vineyards the North Fork has to offer. Simply arrive, unwind, and enjoy the waterfront lifestyle you've been dreaming of.

80 Rabbit Lane, East Marion
$795,000
1026672 MLS
Life's better on the sound! This sound-front lot boasts 50’ of waterfront and approved plans for a 3-bedroom, 2-bath home. Imagine mornings on the porch, afternoons on the water, and evenings with a front-row seat to the most spectacular sunsets around. Whether you're building your forever home, a weekend retreat, or an investment property, this lot is ready when you are and offers the best of North Fork living—just minutes from beautiful beaches, award-winning vineyards, marinas, renowned restaurants, farm stands, boutique shopping.

55915 County Road 48, Greenport
$799,000
3 Beds ⋅ 1 Baths ⋅ 1028101 MLS
Super Cute Greenport Village home packed with charm and character. Walking distance to downtown. 3 bedrooms, 1 bath, diving area, kitchen and living area all on 1st floor with 3 bedrooms and a full bathroom above. Full walk out Basement and fenced in yard. Close to downtown Greenport, Marinas, Golf, restuarants and wineries.

308 Monsell Place, Greenport
$1,695,000
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
$295,000
1 Beds ⋅ 1 Baths ⋅ 1026077 MLS
Enjoy easy living in this 1-bedroom, 1-bath co-op, located just a short walk from the charming Village of Greenport. This move-in-ready home features a newly updated kitchen with modern appliances, a renovated bathroom, and fresh finishes throughout. Perfectly situated to enjoy everything the North Fork has to offer, you'll be just minutes from beautiful beaches, award winning wineries, boutique shopping, restaurants and waterfront attractions.

1000 9th Street Unit #43, Greenport
$1,375,000
3 Beds ⋅ 2 Baths ⋅ 1024020 MLS
Perfectly positioned between Greenport and Southold, this classic cedar-shingled Cape offers an easygoing North Fork lifestyle with beaches, restaurants, and village amenities just minutes away. Inside, the first-floor open plan is anchored by a fireplace and a large kitchen flooded with natural light. Multiple sliding doors lead to a generous wraparound deck, outfitted for dining, lounging, and entertaining. An expanded second floor is devoted to a spacious primary suite with seperate office and a large ensuite bathroom. The backyard invites summer afternoons around the bocce court, and peekaboo water views across the street subtly remind of the home's coastal setting. A full basement provides great utility and flexibility. Comfortable, stylish, unpretentious, and exceptionally well-located, this home is as well-suited to weekends as it is to everyday living.

1050 Bayview Avenue, Southold
$999,000
2 Beds ⋅ 1 Baths ⋅ 1017744 MLS
The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by. Located on a dead-end street on Hashamomuck Pond, this home offers a private dock, 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy boating, kayaking, paddleboarding, fishing, and swimming right out your back door. Surrounded by the gorgeous Southold beaches, over 40 wineries, and local farms, the North Fork has it all. Make it a vacation or year-round home, this is the lifestyle you have thought about, why not make it happen now!

136 Bayview Avenue, Southold
$2,995,000
7 Beds ⋅ 7 Baths ⋅ 1016379 MLS
UNDER CONSTRUCTION - IN PHASE 3 - PROPERTY IS CLOSED IN, ROUGHED IN AND CLOSING IN WALLS - NOW AVAILABLE FOR PRIVATE IN PERSON VIEWINGS - Introducing an exceptional opportunity to own a brand new construction home in Greenport’s coveted Eastern Shores where North Fork charm meets modern luxury living. Don't miss this opportunity to claim for yourself this thoughtfully designed, currently under construction and anticipated to be completed summer 2026 in time for your East End getaway. This stunning seven bedroom six and half bath residence offers 4,310 sqft of refined living space designed with no desire left unrecognized. From the moment you arrive, you’ll appreciate the timeless architectural detail, modern farmhouse feel with a blend of contemporary finishes throughout. The open concept is ideal for entertaining featuring a chefs kitchen with oversized island, premium appliances, abundant cabinet space and butler pantry all flowing effortlessly into the spacious living room, formal dining room or out to the rear covered porch. Seven generously sized bedrooms include an expansive primary suite with oversized bathroom, walk in closet and private second story deck overlooking the backyard. Four of the bedrooms including the primary are on the second level, one bedroom on the main level and two bedrooms are located in the lower level all situated with their own respective bathrooms with the mindfulness around a main level bedroom with en suite full bath. Additional features in the build include a finished walk out lower level with recreational room, in ground vinyl pool and a detached two car garage. This beautifully crafter modern farmhouse is situated between the tranquil Inlet Pond and the beloved Kontokosta Winery also just minutes from the vibrant downtown of Greenport Village. This property is located on the north end of Tasker lane alongside a cleared public pathway with just a 2 minute walk to the famed 67 Step Beach of Greenport. Whether you’re seeking a year round residence, a second home or a vacation rental investment, 1050 Tasker Lane delivers a rare combination of location, luxury, and lifestyle on the North Fork.

1050 Tasker Lane, Greenport
$5,695,000
4 Beds ⋅ 5 Baths ⋅ 1012436 MLS
Introducing a stunning waterfront estate on the Long Island Sound, now available for the first time from its original owners. This coastal gem, located in the North Fork, is situated in one of the most sought-after and picturesque areas on the East End. Nestled on nearly 2 acres, this 4,500 sq. ft. residence offers exceptional views and over 200 feet of private waterfront. The spacious open floor plan includes a junior primary ensuite on the first floor, featuring a separate entrance, a wrap-around covered porch, and direct access to the backyard. The gourmet kitchen is designed to capture breathtaking coastal views, boasting custom cabinetry, high-end appliances, beautiful granite countertops, and a spacious island with seating. Al fresco dining is made easy through the breezeway, which leads to the inviting patio and outdoor decks. The living room and dining room, enhanced by a central fireplace, are filled with natural light and feature beautiful wood floors. Tucked behind the fireplace and accessed through sliding barn doors, the home office offers water views and separate access to the yard. Upstairs, the primary bedroom features a balcony and an ensuite bathroom, showcasing stunning views. Additional bedrooms with balconies, a full bathroom, and a bonus space ensure privacy and comfort for guests. An oversized lounge, also with a waterside balcony and fireplace, connects to the kitchen below via a private staircase, creating an ideal space for a quiet retreat. The spacious art studio, built as part of the expansion, has cork flooring and a wall of windows overlooking the outdoor entertaining space, which includes a fully equipped custom kitchen, dining area, stunning pool, and spa amenities. The yard's mature landscaping and expansive lawn create a welcoming atmosphere for gatherings, with curated spaces for relaxation, including Adirondack chairs nestled along the coastline to enjoy the breathtaking sunsets. Additional amenities include an attached garage, greenhouse, a full unfinished basement with side yard access, and a generator. This property is conveniently located near Greenport Village, wineries, farms, and the bucolic landscape that exemplifies the essence of the North Fork region.

160 Sound Drive, Greenport
$929,000
1 Beds ⋅ 1 Baths ⋅ 1004839 MLS
Charming Cedar Shake Cottage on a Desirable Corner Lot. Enjoy it Now, and/or Expand Extensively in the Future with Proper Permits. The Spacious Deck, Brick Patio, Mature Landscaping, and Lush Shrubbery Create a Private and Secluded Backyard Retreat. Just 3–4 blocks to Beautiful Bay Beaches and 6 Blocks to Greenport Village, Marina, Shops, Restaurants, and NYC Transportation. Start Living the Good Life in Greenport Now. 1100 7th Street, Greenport is also known as 702 Linnet Street, Greenport.

1100 7th Street, Greenport
$935,000
3 Beds ⋅ 2 Baths ⋅ 1004231 MLS
Just a stone's throw from the sands of Town Sound Beach, this bright and airy retreat offers the perfect blend of coastal proximity and quiet privacy. Freshly painted inside and out, the home feels crisp and modern, anchored by a stunning living room featuring cathedral ceilings, a cozy wood-burning fireplace, and oversized windows that flood the space with natural light. The layout is designed for easy flow, boasting a large open kitchen and a formal dining room where sliders lead out to a brand-new deck—perfect for morning coffee or evening hosting. Three strategically placed skylights ensure the interior stays sun-drenched all day long. For those working from home, the dedicated office provides a quiet, professional sanctuary. The primary suite serves as a true escape with its own ensuite bath, complemented by two additional spacious bedrooms and a second full bathroom. Downstairs, the massive basement with 10-foot ceilings and Bilco doors offers incredible potential for a gym, media room, or extra storage. Outside, the .78-acre property is a total dream. The manicured gardens and park-like setting create a lush backdrop for the expansive wood deck, offering a serene environment to relax after a day at the beach. It’s a rare find that perfectly balances large-scale rooms with a warm, inviting soul.

100 Bayberry Lane, Southold
$2,399,000
4 Beds ⋅ 4 Baths ⋅ 1000563 MLS
Welcome to your luxury retreat on the North Fork, ideally located in the hamlet of Greenport. This brand new residence offers the perfect blend of sophisticated design, modern comfort and effortless indoor-outdoor living - all just moments from the Long Island Sound with deeded beach rights to a private community beach. Your days can begin with morning walks along the shoreline and end with memorable sunsets. This 2,250 square foot home features an airy open concept floor plan anchored by a gourmet chef’s kitchen with premium finishes and generous entertaining space. The first floor includes a beautifully appointed junior suite, ideal for guests or multigenerational living. Upstairs, the primary suite offers a spa inspired bath, accompanied by two additional bedrooms and a full bathroom. Designed for effortless indoor outdoor living, the backyard is an entertainer’s dream with a spacious patio and a heated saltwater pool. A rear basement entrance adds convenience and flexibility for storage, recreation, or future expansion. Experience refined coastal living in one of Greenport’s most desirable locations—where luxury, comfort, and the Sound’s natural beauty come together. Currently under construction with completed in Fall 2026

1760 McCann Lane, Greenport
$839,000
3 Beds ⋅ 3 Baths ⋅ 926613 MLS
Spacious Cape with Garage, Nice Yard and Inground Pool, Ideally Located Near a Memorable Long Island Sound Beach. The Property Backs Up to a Scenic Waterfront Vineyard with Tasting Room, While Greenport Marinas, Boat Launches, Village Shops and Restaurants Are All Nearby.

28 (aka 710) Sound Road, Greenport
$1,276,000
3 Beds ⋅ 3 Baths ⋅ 998976 MLS
Welcome to 550 Madison Avenue in Greenport, a thoughtfully designed New Construction farmhouse that feels comfortable from the moment you arrive. The covered front porch is more than an architectural detail. There is actually room for a chair and side table, creating the perfect spot for a quiet morning coffee. Inside, wide 6-inch oak floors connect the bright, open living spaces. The powder room is conveniently located near the front entrance, but it is tucked far enough away from the open living room, dining area, and kitchen to give everyone a little privacy when the house is full. The custom kitchen design brings together the features buyers keep asking for, including a paneled refrigerator, a full pantry closet, open shelving, generous cabinetry, and a kitchen sink positioned beneath a window overlooking the backyard. Even doing the dishes comes with a view of the established maple trees. A full glass slider in the dining area fills the back of the home with natural light and creates an easy connection to the outdoor entertaining spaces and grill. The backyard views can also be enjoyed from the living room, making the surrounding landscape feel like part of the interior design. Upstairs, the primary bedroom features a peaceful en-suite bathroom with distinctive tile flooring and calm, carefully selected finishes. Even the first-floor powder room has beautiful wallpaper, adding personality and making this New Construction home feel intentional rather than predictable. The fully fenced backyard is surrounded by established maple trees, creating a quiet and private setting that feels like a hidden corner of Greenport. The newly installed stone patio includes an outdoor cushioned conversation area, a separate outdoor dining patio, and a dedicated fire pit for evenings under the trees. There is also room to explore the possibility of adding a pool without making the yard feel crowded. The location brings the North Fork lifestyle within easy reach. The Greenport LIRR station and Hampton Jitney stop are approximately half a mile away for convenient transportation to New York City. Aldo’s Coffee is about a three-minute bike ride or a ten-minute walk, with Greenport Village shops, restaurants, waterfront destinations, and local beaches all close enough to enjoy without always getting back into the car. New Construction, a custom kitchen, paneled appliances, wide oak floors, en-suite bathrooms, a fenced backyard, mature trees, outdoor entertaining spaces, and easy access to Greenport Village. This might be the one you have been waiting for. You really need to come see it. In the evening it sparks with fireflies to capture summer vibes in Greenport Village.

550 Madison Avenue, Greenport
$1,849,000
4 Beds ⋅ 3 Baths ⋅ 942025 MLS
Greenport Gem — Timeless Elegance & Coastal Living Tucked privately behind tall hedges on a beautifully landscaped, gated corner property, this stately 1930s American Square offers an exceptional blend of historic character, refined comfort, and the coveted Greenport lifestyle. Meticulously restored in 2012 and gently lived in since, the home retains its original woodwork, doors, and flooring, preserving the craftsmanship and character of a bygone era while offering modern comforts, including central air conditioning. A spacious kitchen flows effortlessly into the inviting living areas, creating a warm and sophisticated setting for entertaining and relaxed everyday living. Outside, the lush grounds create a private oasis with mature landscaping, generous outdoor space, and ample room for a pool. A detached 440-square-foot garage offers additional flexibility and convenience. Just moments from Greenport’s sandy 4th, 5th, and 6th Street bay beaches and parks, and close to the Village’s celebrated shops, restaurants, marinas, and NYC transportation, this distinctive property presents a rare opportunity to enjoy timeless architecture, exceptional privacy, and effortless coastal living in one of the North Fork’s most desirable destinations. See Photos or Attachment for Floor Plan and Survey.

1025 9th Street, Greenport
$2,700,000
3 Beds ⋅ 3 Baths ⋅ 995366 MLS
A Rare Opportunity!!! This incredible property boasts 1.75 private acres on the Long Island Sound. Enjoy spectacular unobstructed views, from an elevated position, of the pristine shoreline, the beautiful waves, and the Connecticut coast, private access to your own beach, and much much more. The long driveway brings you to an almost secluded hideaway with some of the finest water views on Long Island. The home itself offers a sun-filled living room with a fireplace and dining area, both featuring floor to ceiling windows which show off the magnificent seascape. The home also hosts an eat-in-kitchen, 3 bedrooms, 3 baths, a large basement, an oversized 2 car garage, and a large deck to enjoy the breathtaking scenery. If being on the water is for you, you've arrived. Don't miss this one time opportunity.

100 Sound Drive, 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
$1,297,000
4 Beds ⋅ 2 Baths ⋅ 980655 MLS
Prime location legal 2-family featuring 2 separate 2-bedroom units. An exceptional opportunity for an end user seeking supplemental rental income or for an investor pursuing a desirable multi-unit asset. Set amid the charm of sought-after Greenport Village, this versatile property features a porch, deck, patio, and 1-car garage, along with additional outdoor amenities including a cabana and hot tub, all conveniently located near local restaurants, shopping, and transportation.

407 Wiggins Street, Greenport
$1,297,000
4 Beds ⋅ 2 Baths ⋅ 980657 MLS
Prime location legal 2-family featuring 2 separate 2-bedroom units. An exceptional opportunity for an end user seeking supplemental rental income or for an investor pursuing a desirable multi-unit asset. Set amid the charm of sought-after Greenport Village, this flexible property offers central air conditioning, front porch, deck, and patio, all conveniently close to local restaurants, shopping, and transportation. Turnkey appeal and income-producing potential enhance this compelling offering.

401 Wiggins Street, Greenport
$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
$485,000
977929 MLS
Wonderful opportunity to build a Residential Home in the highly-desirable and sought-after Town of Greenport! Greenport offers a vast array of Art Galleries, Museums, Fishing Charters, Boutique Shops, Breweries and Cideries, Waterfront Dining and other Entertainment Venues. This generously sized .67 Acre Level Parcel is just waiting for you to create that special home you've always been dreaming of! Live the lifestyle you so richly deserve on the beautiful North Fork of Long Island! Take advantage of this exciting offering today!!

620 Kerwin Boulevard, 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

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.