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$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
$1,785,000
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
$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 Ninth Street Unit #43, Greenport
$1,095,000
3 Beds ⋅ 2 Baths ⋅ 1021578 MLS
Charming 1920's farmhouse located in the heart of Greenport Village. Three blocks from Jitney/LIRR, restaurants, shops, galleries and Greenport's historic waterfront. 3 beds, 2 full baths, wide plank hardwood floors, updated kitchen, plumbing and electric. Attractive backyard with southern exposure. Ready to move right in and enjoy all Greenport and the North Fork has to offer. Close to town, beach and public transport.

217 Center Street, Greenport
$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 4,544 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
$949,000
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
$799,900
3 Beds ⋅ 2 Baths ⋅ 1010914 MLS
Renovated 1910 Colonial with Open Floor Plan. Down the Road From Town Beach. Just a Short Bike Ride to Down Town Greenport and Wineries !! Possibility of Selling Fully Furnished !! Large Back Building Could Be Turned into a Pool House, Garage or Shed, Additional information: Appearance Diamond, Interior Features: Living Rm, Dining Area, Spacious Eat in Kitchen with Large Island, Breakfast Nook, 3 Bedrooms(Small one on First Floor, 2 On 2nd Floor), 1.5 Renovated Bathrooms. Separate Hotwater Heater, 2 Separate Driveways SELLER IS APPLYING FOR PERMIT AND VARIANCE FOR A INGROUND POOL, HE IS SELLING WITH PERMIT ONLY FOR IT NOT INSTALL.

275 Sound Road, Greenport
$1,579,000
3 Beds ⋅ 2 Baths ⋅ 1008089 MLS
A Turn of the century well preserved 3 BR 2 Bath period home in the sought after Greenport Village. A spacious parcel with a two car garage, a secluded peaceful garden, work shed and a large private rear deck. The interior features include a formal dining room, a large kitchen with cathedral ceilings, a newly renovated bath, original pine flooring, and a delightful sun room, plus the classic front porch. All In close proximity to the Village beaches, Peconic Bay and transportation to NYC. This property is ready to welcome the next resident.

311 5th Street, Greenport
$1,285,000
3 Beds ⋅ 2 Baths ⋅ 999868 MLS
Some houses get a coat of paint and call it a day, 611 aka 175 Maple Street got a full designer renovation! This charming house is just a short stroll from Greenport Village waterfront restaurants, boutiques & beaches. This home delivers the warmth of classic architecture with a modern flair. Enter through the front door and the character hits first: hardwood floors throughout, recessed lighting overhead, and high-end finishes that make every room feel curated rather than constructed. The first floor flows easily between a thoughtfully designed living space and a kitchen equipped with stainless steel high end appliances and clean lines. Enjoy a cozy sun-room overlooking the backyard and a bonus space off the kitchen, which could have many uses including an office or flex space. Up-stairs, the entire second floor is dedicated to a spacious primary suite removed from the rest of the home in the best way possible! The primary suite spans the full upper level...a genuine retreat with vaulted ceilings with wood beams and its own en-suite bathroom including radiant heat in the floors and designer finishes. Two additional bedrooms on the main floor keep family and guests comfortable without compromise. Outside, the transformation continues. Bluestone pavers trace the front walkway and wrap the back patio. There is a detached cedar shake garage that is also freshly renovated. The ample driveway, which is crushed natural stone handles guests effortlessly- a rare feature for Greenport! Every system, the electric, plumbing, HVAC is brand new. Truly a turnkey getaway in one of the best locations in Greenport!

175 AKA 611 Maple Street, Greenport
$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
$879,000
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
$1,377,000
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
$1,849,000
4 Beds ⋅ 3 Baths ⋅ 942025 MLS
Greenport Gem - Renovated American Square. Gated and Nestled Behind Tall Hedges for Privacy on a Large Corner Lot with Room for Pool, You Will Find This Fully Restored (2012) and Gently Lived-In Stately 1930's Classic. The Original Woodwork, Doors and Flooring are Preserved Throughout the Home. Take a Step Back in Time but With All the Modern Conveniences (including Central Airconditioning). Close to the 4th, 5th and 6th Street Bay Beaches and Parks, Village Shops and Restaurants and NYC Bus and Train. See Photos or Attachment for Floor Plan.

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
$1,199,000
4 Beds ⋅ 2 Baths ⋅ 985147 MLS
Welcome to this charming cape, a true gem with its private beach and inviting swimming pool. This sweet home features 4 bedrooms and 2 full baths, combining easy living and casual comfort . Spacious, sunlit rooms provide ample living space for relaxation and entertaining. Cozy up by the fireplace in the living room, or retreat to the den for a quiet evening with a book or movie. The open-concept kitchen seamlessly connects to the living room. Large bedrooms, convenient first-floor laundry and home office complete the interior. The breathtaking backyard steals the show, with a stunning inground pool perfect for hot summer days, lush landscaping ensures privacy, making the firepit area a perfect spot for unwinding and enjoying outdoor serenity. The private community beach offers peaceful moments by the water. This location is ideal for sunset strolls or weekend fun., Additional information: Appearance:very good

130 Tasker Lane, Greenport
$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
$1,297,000
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
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 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 with the "prettiest backyard in Greenport", 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
$2,999,999
4 Beds ⋅ 7 Baths ⋅ 968387 MLS
"Precision In Every Detail. Elevated Living Throughout" - Set within a private enclave moments from the Peconic Bay, this newly constructed home delivers a refined living experience defined by custom craftsmanship, scale, and seamless indoor-outdoor flow. Every element has been thoughtfully curated, blending clean architectural lines with bespoke materials and elevated finishes throughout. At the heart of the home, a striking chef’s kitchen anchors the main living space—appointed with quartz countertops, custom white oak cabinetry with lighting, Kohler workstation sink and a full suite of Miele appliances. Designed for both everyday living and elevated entertaining, the open-concept layout transitions effortlessly into expansive living and dining areas, where soaring ceilings, abundant natural light, solid white oak wood 6" plank floors and a custom stone fireplace anchored by bookcases create a warm yet sophisticated atmosphere. Bedrooms and bathrooms are designed as private retreats, featuring refined finishes, generous proportions, and a calm, modern aesthetic. A first floor primary ensuite offers the ultimate in convenience and privacy, creating a true main level retreat with exceptional finishes, flawless primary bathroom, expansive custom finished walk in closet and all with a well proportioned layout. The outdoor setting is equally compelling, offering a resort-inspired setting complete with a heated saltwater pool with custom waterfall, expansive bluestone slate patio, and built-in fireplace—ideal for hosting or unwinding in total privacy. The offering is further elevated by private association beach access to the Peconic Bay, perfectly suited for effortless trips by golf cart, which is included, creating a seamless connection between home and shoreline. Every detail, from the curated landscaping to the integrated lighting, enhances both ambiance and usability from day to evening. The home is equipped with a fully integrated custom home automation system, delivering intuitive control over lighting, climate, sound, and security. A generator hook up will ensure uninterrupted comfort, while thoughtful additions such as a golf cart—perfect for easy access to nearby waterfront and community amenities—further elevate the lifestyle offering. Each space reflects the same level of detail and intention found throughout the home. An unmatched opportunity to own a turnkey, showstopping residence where design, technology, and lifestyle converge—crafted for those who value both precision and presence.

250 Osprey Nest Road, 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
$2,500,000
976851 MLS
Built in 1894 by Charles Corwin for the remarkable Sara Adams, who financed it to bring culture and community to Greenport Village, this Queen Anne auditorium is one of the North Fork's most significant historic structures. For over four decades, it served as the center of village life, hosting drama, vaudeville, and live music before quietly transitioning to commercial use. Situated on a prime corner lot in Greenport's commercial district, the building offers over 6,000 square feet of interior space with an extraordinary degree of historic integrity: the original stage, basement dressing rooms, and curved balcony with ornate metal grillwork all remain intact, a rarity for a building of this age and type. This is a genuine opportunity to steward a piece of Greenport's identity and write the next chapter for a building that was always meant to be at the heart of the community.

434 Main Street, 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
$559,000
1 Beds ⋅ 1 Baths ⋅ 969086 MLS
This can be your piece of paradise on the East End of Long Island - Welcome to 31 Sage Boulevard! This one-of-a-kind, exquisite and picturesque gated community consists of 89 prime acres surrounded by the waters of the Little Peconic Bay. Upon entering the community, it will bring you back to the historical dwelling of beach cottages that have their own private beach, marina and club house. The Breezy Shores beachfront community is a co-op consisting of 31 individual and unique dwellings some of which have been modernized and expanded upon. Upon entering the front door of 31 Sage Boulevard you enter a versatile room that has plenty of space to be used as a bedroom to include a queen size bed. The dwelling has a full bathroom, a galley kitchen, ample storage and an outside shower. From all rooms in the house you have unobstructed views of the bay. While sitting in the yard, capture the beautiful setting, sea breezes and the scenic arena that a small bayfront community has to offer. The property is within close proximity to both Southold and Greenport Villages, LIRR, Vineyards and exceptional beaches. The property is in a seasonal community open from April 1 through November 1. A piece of paradise awaits you here at 31 Sage Boulevard for the Summer of 2026!

31 Sage Boulevard Unit #31, Greenport
$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
$1,325,000
3 Beds ⋅ 3 Baths ⋅ 950921 MLS
Experience the pinnacle of refined living in this completely reimagined home, boasting a comprehensive renovation and redesign led by a professional interior designer. Every square inch has been thoughtfully curated, starting with the custom front door featuring openable screened sidelights that welcome you inside. Premium oak hardwood flooring flows seamlessly throughout the main living areas, grounding the home in natural warmth and elegance. The heart of the home, the great room and large kitchen, is an entertainer's dream, featuring gas fireplace, a dry bar with a wine fridge, premium lighting and plumbing fixtures, quartz countertops and custom window treatments including blinds and valances. First floor also includes a light filled den and separate office space for working at home. Retreat to the spectacular owner’s suite, a true sanctuary defined by architectural ceilings with shiplap details and a custom walk-in closet. The en-suite bathroom is clad in Italian marble and featuring premium fixtures. Indulge in the luxury of radiant floor heating—which extends into the large, curbless spa shower with its sleek infinity drain. Your guests are treated to equal luxury; guest baths feature premium fixtures and their own radiant floor heating. The guest bedrooms offer cozy carpeting and custom woodworking with the twin room featuring blackout and light-filtering shades for perfect rest. Behind the walls, the home is just as impressive. A whole-house water softening and purification system, smart irrigation system, and 2-zone heat/AC with smart thermostats ensure comfort and peace of mind. This is more than a renovation; it is a complete lifestyle upgrade. Located close to the heart of downtown Greenport Village and its bayfront beaches and transportation hub.

55 Brown Street, 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.