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A view that can't be beat! Wake up to the sounds of waves crashing, and end your night with one of the most breathtaking sunsets on Long Island's North Fork. This ranch is located directly on the water, and features 2 bedrooms and 2 full bathrooms. The open concept kitchen and living area are surrounded by windows, where you feel as if you are floating in the water. The side door opens to a deck large enough for a grill, table and chairs. Truly the perfect spot to enjoy an outdoor summer dinner, with food sourced from the many local farm stands, and a bottle of wine from one of the North Fork's esteemed vineyards located less than a mile away. The side deck also has a staircase that allows direct access to your personal beachfront area - providing easy access to the water where you can swim, fish, kayak, paddle board and more!

2 Beds ⋅ 2 Baths ⋅ 931892 MLS

A view that can't be beat! Wake up to the sounds of waves crashing, and end your night with one of the most breathtaking sunsets on Long Island's North Fork. This ranch is located directly on the water, and features 2 bedrooms and 2 full bathrooms. The open concept kitchen and living area are surrounded by windows, where you feel as if you are floating in the water. The side door opens to a deck large enough for a grill, table and chairs. Truly the perfect spot to enjoy an outdoor summer dinner, with food sourced from the many local farm stands, and a bottle of wine from one of the North Fork's esteemed vineyards located less than a mile away. The side deck also has a staircase that allows direct access to your personal beachfront area - providing easy access to the water where you can swim, fish, kayak, paddle board and more!

58315 North Road, Greenport

$945,000

A unique opportunity set on 3.3 acres in the heart of Greenport. This two-bedroom residence was cleverly designed with future expansion in mind, while offering an easy-to-maintain home in its current form just minutes from the beach and Greenport’s commercial center. The house sits on a cleared 1.7-acre residential parcel with beautiful specimen trees and a vegetable garden, while the neighboring 1.6-acre wooded lot can be used for agriculture or preserved as a natural buffer to neighboring properties, providing exceptional privacy and a tranquil setting. Ideal for those envisioning a larger future project while still deriving immediate utility from the property, or for buyers seeking an easy Greenport pied-a-terre with acreage, privacy, and room to grow.

2 Beds ⋅ 1 Baths ⋅ 999762 MLS

A unique opportunity set on 3.3 acres in the heart of Greenport. This two-bedroom residence was cleverly designed with future expansion in mind, while offering an easy-to-maintain home in its current form just minutes from the beach and Greenport’s commercial center. The house sits on a cleared 1.7-acre residential parcel with beautiful specimen trees and a vegetable garden, while the neighboring 1.6-acre wooded lot can be used for agriculture or preserved as a natural buffer to neighboring properties, providing exceptional privacy and a tranquil setting. Ideal for those envisioning a larger future project while still deriving immediate utility from the property, or for buyers seeking an easy Greenport pied-a-terre with acreage, privacy, and room to grow.

427 Sound Road, Greenport

$940,000

Built in 1868, this historic Greenport Village home is brimming with character and ready for its next chapter. Set on a .25-acre lot, the home features large spacious rooms, 3 bedrooms, 1.5 baths, beautiful built-ins, and a wood-burning stove. The home presents an exciting opportunity for thoughtful restoration and personalization, allowing the next owner to enhance and reimagine the space while honoring its original details. A rear deck extends the living space outdoors, while a substantial barn at the back of the property opens the door to endless potential as a studio, workshop, or inspired retreat. The expansive yard provides room to entertain, garden, or simply enjoy the privacy and openness seldom found within the village. Ideally located just a short distance to Greenport’s vibrant shops, restaurants, park, waterfront, bay beach, LIRR & Hampton Jitney. A unique opportunity to own a piece of Greenport history with space, flexibility, and an unbeatable village lifestyle.

3 Beds ⋅ 2 Baths ⋅ 956373 MLS

Built in 1868, this historic Greenport Village home is brimming with character and ready for its next chapter. Set on a .25-acre lot, the home features large spacious rooms, 3 bedrooms, 1.5 baths, beautiful built-ins, and a wood-burning stove. The home presents an exciting opportunity for thoughtful restoration and personalization, allowing the next owner to enhance and reimagine the space while honoring its original details. A rear deck extends the living space outdoors, while a substantial barn at the back of the property opens the door to endless potential as a studio, workshop, or inspired retreat. The expansive yard provides room to entertain, garden, or simply enjoy the privacy and openness seldom found within the village. Ideally located just a short distance to Greenport’s vibrant shops, restaurants, park, waterfront, bay beach, LIRR & Hampton Jitney. A unique opportunity to own a piece of Greenport history with space, flexibility, and an unbeatable village lifestyle.

506 5th Street, Greenport

$940,000

Welcome to August Acres – A Tranquil Retreat Near Greenport Nestled just a short distance from the charming Village of Greenport. This colonial-style home offers a perfect blend of comfort and convenience. Situated in a quiet and serene location, this beautifully maintained property is move-in ready and ideal for both relaxation and entertainment. The first floor features a spacious living room, an inviting eat-in kitchen, a formal dining room, and plenty of closet space. A conveniently located laundry room and a half bath complete this level. Upstairs, the home boasts four generously sized bedrooms, including a primary suite with its own bath, along with an additional full bathroom. Step outside to enjoy a wonderful backyard—perfect for summer gatherings, outdoor dining, or simply unwinding in your own private retreat. The private association bay beach is a short distance from this home. It is wonderfully peaceful, with the soft sand beneath your feet and the waves gently lapping at the shore. The perfect spot to relax and soak in the beauty of the water. Don’t miss the opportunity to make August Acres your new home!

4 Beds ⋅ 3 Baths ⋅ 869285 MLS

Welcome to August Acres – A Tranquil Retreat Near Greenport Nestled just a short distance from the charming Village of Greenport. This colonial-style home offers a perfect blend of comfort and convenience. Situated in a quiet and serene location, this beautifully maintained property is move-in ready and ideal for both relaxation and entertainment. The first floor features a spacious living room, an inviting eat-in kitchen, a formal dining room, and plenty of closet space. A conveniently located laundry room and a half bath complete this level. Upstairs, the home boasts four generously sized bedrooms, including a primary suite with its own bath, along with an additional full bathroom. Step outside to enjoy a wonderful backyard—perfect for summer gatherings, outdoor dining, or simply unwinding in your own private retreat. The private association bay beach is a short distance from this home. It is wonderfully peaceful, with the soft sand beneath your feet and the waves gently lapping at the shore. The perfect spot to relax and soak in the beauty of the water. Don’t miss the opportunity to make August Acres your new home!

370 Pheasant Place, Greenport

$927,500

Enjoy the best of North Fork living in Greenport’s sought-after August Acres community. This meticulously maintained 3-bedroom, 2-bath ranch sits on a shy acre, offering exceptional privacy and ample room to create your own backyard retreat — including space for a pool. Thoughtful updates enhance the home’s comfort and appeal, including fresh interior paint (2026), a new deck, an updated kitchen, and a new heating system. The spacious den, featuring a wood-burning fireplace and sliding doors to the deck, provides an inviting setting for relaxing or entertaining. Additional highlights include a primary en-suite with a generous bath and walk-in closet, a bright living room, dining area, convenient laundry room, full basement and a 2-car garage. Residents also enjoy access to the association’s deeded bay beach — the perfect spot to experience the beauty of North Fork living. This house checks off all the boxes. Restaurants, shopping, farm stands, wineries, breweries, boating... you name it. It's all right there.

3 Beds ⋅ 2 Baths ⋅ 1015877 MLS

Enjoy the best of North Fork living in Greenport’s sought-after August Acres community. This meticulously maintained 3-bedroom, 2-bath ranch sits on a shy acre, offering exceptional privacy and ample room to create your own backyard retreat — including space for a pool. Thoughtful updates enhance the home’s comfort and appeal, including fresh interior paint (2026), a new deck, an updated kitchen, and a new heating system. The spacious den, featuring a wood-burning fireplace and sliding doors to the deck, provides an inviting setting for relaxing or entertaining. Additional highlights include a primary en-suite with a generous bath and walk-in closet, a bright living room, dining area, convenient laundry room, full basement and a 2-car garage. Residents also enjoy access to the association’s deeded bay beach — the perfect spot to experience the beauty of North Fork living. This house checks off all the boxes. Restaurants, shopping, farm stands, wineries, breweries, boating... you name it. It's all right there.

2675 Kerwin Boulevard, Greenport

$899,000

Exquisitely renovated, this charming cedarshake Craftsman, in the seaport village of Greenport, is filled with light. From the airy front sunroom porch, to the spacious living room, formal dining room, and eat-in kitchen, this enchanting Arts & Crafts Cottage also boasts a huge primary ensuite bedroom with walk-in closet on the 2nd floor, another large bedroom on the first floor and two more flex rooms that can be used as offices, dens, or overspill guest bedrooms. The laundry room is on the first floor as is the 2nd full bathroom. A sweet and private backyard, edged with Privet, backs up to the one-car garage. This lovely property is across the street from the Greenport School with its playing fields and track and a short distance from the 6th Street Beach, Village shopping and restaurants, and the transportation hub where you can catch the train or Jitney to Manhattan or the ferry to Shelter Island & the South Fork.

3 Beds ⋅ 2 Baths ⋅ 957568 MLS

Exquisitely renovated, this charming cedarshake Craftsman, in the seaport village of Greenport, is filled with light. From the airy front sunroom porch, to the spacious living room, formal dining room, and eat-in kitchen, this enchanting Arts & Crafts Cottage also boasts a huge primary ensuite bedroom with walk-in closet on the 2nd floor, another large bedroom on the first floor and two more flex rooms that can be used as offices, dens, or overspill guest bedrooms. The laundry room is on the first floor as is the 2nd full bathroom. A sweet and private backyard, edged with Privet, backs up to the one-car garage. This lovely property is across the street from the Greenport School with its playing fields and track and a short distance from the 6th Street Beach, Village shopping and restaurants, and the transportation hub where you can catch the train or Jitney to Manhattan or the ferry to Shelter Island & the South Fork.

803 Front Street, Greenport

$860,000

Greenport Colonial Close To Village. This inviting Greenport Colonial offers 4 bedrooms and 3 full baths, blending comfort with a prime location. Set on a spacious lot, the home features a welcoming front yard, a fenced backyard with newly refinished hardwood floors, and a new deck-ideal for summer gatherings. Conveniently located close to Greenport Village, you’ll enjoy easy access to shops, restaurants, public transportation, golf, beaches, vineyards, breweries, the North Ferry, and local schools. Whether as a year-round residence or a seasonal getaway, this property provides the perfect balance of lifestyle, location, and leisure in the heart of the North Fork.

4 Beds ⋅ 3 Baths ⋅ 916687 MLS

Greenport Colonial Close To Village. This inviting Greenport Colonial offers 4 bedrooms and 3 full baths, blending comfort with a prime location. Set on a spacious lot, the home features a welcoming front yard, a fenced backyard with newly refinished hardwood floors, and a new deck-ideal for summer gatherings. Conveniently located close to Greenport Village, you’ll enjoy easy access to shops, restaurants, public transportation, golf, beaches, vineyards, breweries, the North Ferry, and local schools. Whether as a year-round residence or a seasonal getaway, this property provides the perfect balance of lifestyle, location, and leisure in the heart of the North Fork.

210 Bennet Road, Greenport

$850,000

Welcome to this charming Farmhouse/Colonial in one of Greenport’s most desirable in-town neighborhoods. Just moments from sandy beaches, award-winning restaurants, boutique shops, and the harbor, this home offers the perfect blend of village lifestyle and quiet residential living.Enjoy 4 bedrooms all privately set on the second level, including a spacious primary bedroom with a cozy loft. Sunlight fills the home through classic windows that complement the warmth of wood floors throughout. The inviting first floor features an eat-in kitchen with granite countertops, stainless steel appliances, and a pantry, along with the convenience of a first-floor laundry room. Step outside onto the Trex front porch or unwind on the Trex back deck overlooking the backyard — ideal for grilling and casual entertaining. Practical upgrades include 3-zone heating, a security system plus Ring camera, generator, newer hot water heater, and oil furnace. An attic above the addition offers excellent storage, and off-street parking accommodates 2–3 vehicles. Perfectly suited as a primary home, weekend retreat, or investment property, this Greenport gem puts the best of the North Fork right at your doorstep.

4 Beds ⋅ 3 Baths ⋅ 942474 MLS

Welcome to this charming Farmhouse/Colonial in one of Greenport’s most desirable in-town neighborhoods. Just moments from sandy beaches, award-winning restaurants, boutique shops, and the harbor, this home offers the perfect blend of village lifestyle and quiet residential living.Enjoy 4 bedrooms all privately set on the second level, including a spacious primary bedroom with a cozy loft. Sunlight fills the home through classic windows that complement the warmth of wood floors throughout. The inviting first floor features an eat-in kitchen with granite countertops, stainless steel appliances, and a pantry, along with the convenience of a first-floor laundry room. Step outside onto the Trex front porch or unwind on the Trex back deck overlooking the backyard — ideal for grilling and casual entertaining. Practical upgrades include 3-zone heating, a security system plus Ring camera, generator, newer hot water heater, and oil furnace. An attic above the addition offers excellent storage, and off-street parking accommodates 2–3 vehicles. Perfectly suited as a primary home, weekend retreat, or investment property, this Greenport gem puts the best of the North Fork right at your doorstep.

735 aka 718 Wiggins Street, Greenport

$849,000

This charming Greenport cottage blends warmth, character, and easy coastal living just moments from Greenport Village. Located only a short stroll from Main Street, shops, restaurants, and the waterfront, it offers the rare combination of village-adjacent convenience while still feeling peaceful and residential. Full of natural charm, the home features a comfortable two-bedroom layout with a relaxed, inviting feel throughout. It’s the kind of space that immediately feels easy to settle into, with potential to enhance over time. Out back, a deck and separate patio create seamless indoor-outdoor living—perfect for morning coffee, summer dinners, or quiet evenings at home. The outdoor space becomes a true extension of the home and adds meaningful lifestyle value. Filled with character and opportunity, this is a special chance to enjoy the best of Greenport living—walkable to everything that makes the village so desirable, yet tucked into a quieter setting with a true North Fork charm.

2 Beds ⋅ 2 Baths ⋅ 995738 MLS

This charming Greenport cottage blends warmth, character, and easy coastal living just moments from Greenport Village. Located only a short stroll from Main Street, shops, restaurants, and the waterfront, it offers the rare combination of village-adjacent convenience while still feeling peaceful and residential. Full of natural charm, the home features a comfortable two-bedroom layout with a relaxed, inviting feel throughout. It’s the kind of space that immediately feels easy to settle into, with potential to enhance over time. Out back, a deck and separate patio create seamless indoor-outdoor living—perfect for morning coffee, summer dinners, or quiet evenings at home. The outdoor space becomes a true extension of the home and adds meaningful lifestyle value. Filled with character and opportunity, this is a special chance to enjoy the best of Greenport living—walkable to everything that makes the village so desirable, yet tucked into a quieter setting with a true North Fork charm.

335 Sterling Place, Greenport

$800,000

Unique opportunity to own a Main Street Retail shop the heart of Historic Greenport. Built in the 1800s and full of charm and history.

921718 MLS

Unique opportunity to own a Main Street Retail shop the heart of Historic Greenport. Built in the 1800s and full of charm and history.

425 Main, Greenport

$799,000

Desirable "West Dublin" locale - an absolutely ideal location in Greenport Village: only three short blocks to bay beach, four blocks to school and six blocks to the center of all the Greenport action - entertainment, fine and fun restaurants, shops and more! Classic Arts & Crafts, renovated but retaining the charm of the architectural style. Light and bright throughout, open plan that flows from the sunny fully closed-in porch to the living room, dining room and kitchen. Hardwood floors throughout, two bedrooms, full bath with a generous linen closet. Full basement that is only waiting for your imagination. Long driveway and detached garage affords off-street parking or possibly a great playroom! Back yard is deep and offers many outdoor possibilities including room for a pool.. Property sold"as is" ...$799,000

2 Beds ⋅ 1 Baths ⋅ 812808 MLS

Desirable "West Dublin" locale - an absolutely ideal location in Greenport Village: only three short blocks to bay beach, four blocks to school and six blocks to the center of all the Greenport action - entertainment, fine and fun restaurants, shops and more! Classic Arts & Crafts, renovated but retaining the charm of the architectural style. Light and bright throughout, open plan that flows from the sunny fully closed-in porch to the living room, dining room and kitchen. Hardwood floors throughout, two bedrooms, full bath with a generous linen closet. Full basement that is only waiting for your imagination. Long driveway and detached garage affords off-street parking or possibly a great playroom! Back yard is deep and offers many outdoor possibilities including room for a pool.. Property sold"as is" ...$799,000

401 6th Street, Greenport

$790,000

Design your ideal residence on this expansive 7.5-acre plot, once belonging to the historic North Road Dairy Farm. Embrace the 1.9-acre designated building area, alongside 5.6 acres of fertile agricultural terrain, perfect for realizing your equestrian ambitions. Discover a charming pond and the iconic original silo gracing this picturesque landscape. Enjoy membership in the esteemed Rock Cove Estates, granting privileged entry to the Long Island Sound private beach. HOA fee $500/year for beach clean up and maintenance of stairs to beach and beach path

L3546493 MLS

Design your ideal residence on this expansive 7.5-acre plot, once belonging to the historic North Road Dairy Farm. Embrace the 1.9-acre designated building area, alongside 5.6 acres of fertile agricultural terrain, perfect for realizing your equestrian ambitions. Discover a charming pond and the iconic original silo gracing this picturesque landscape. Enjoy membership in the esteemed Rock Cove Estates, granting privileged entry to the Long Island Sound private beach. HOA fee $500/year for beach clean up and maintenance of stairs to beach and beach path

67925 North Road, Greenport

$750,000

Charming Village Colonial in the Heart of Greenport! Nestled on one of Greenport’s most sought-after streets, this beautifully maintained Colonial blends historic charm with modern comfort. Featuring approximately 1,800 sq ft of living space, this home offers 5 bedrooms, 2 full baths, and inviting living areas filled with natural light. The updated kitchen boasts stainless-steel appliances, stone countertops, and custom cabinetry perfect for entertaining or everyday living. Enjoy a seamless flow from the dining area to the cozy living room, complete with original details and hardwood floors throughout. The home also includes a full basement, private driveway, and a detached garage for added convenience. Outside, the landscaped yard and patio provide the ideal setting for summer gatherings, gardening, or quiet relaxation. Located just moments from Greenport Village shops, award-winning restaurants, beaches, and the LIRR, this property offers the perfect North Fork lifestyle. Whether as a year-round residence or a weekend retreat.

5 Beds ⋅ 3 Baths ⋅ 931803 MLS

Charming Village Colonial in the Heart of Greenport! Nestled on one of Greenport’s most sought-after streets, this beautifully maintained Colonial blends historic charm with modern comfort. Featuring approximately 1,800 sq ft of living space, this home offers 5 bedrooms, 2 full baths, and inviting living areas filled with natural light. The updated kitchen boasts stainless-steel appliances, stone countertops, and custom cabinetry perfect for entertaining or everyday living. Enjoy a seamless flow from the dining area to the cozy living room, complete with original details and hardwood floors throughout. The home also includes a full basement, private driveway, and a detached garage for added convenience. Outside, the landscaped yard and patio provide the ideal setting for summer gatherings, gardening, or quiet relaxation. Located just moments from Greenport Village shops, award-winning restaurants, beaches, and the LIRR, this property offers the perfect North Fork lifestyle. Whether as a year-round residence or a weekend retreat.

35 Washington Avenue, Greenport

$739,000

Greenport Village Farmhouse Built in 2001, Featuring a New Roof (2020), a Welcoming Front Porch, and a Spacious Yard. This Three-Bedroom Home with One and Half Baths, Offers a Good-Sized Living Room and One Especially Large Bedroom with Double Closet Space. Located within One Block from a Park with Playground and a Park with Basketball Courts. A Waterfront Park and Beach is Just Eight Blocks Away and NYC Transportation is Approximately Five Blocks Away. Enjoy Easy Access to Village Shops, Restaurants, Mitchell Park Carousel, Mitchell Park Marina and So Much More from Your Comfortable Home.

3 Beds ⋅ 2 Baths ⋅ 983659 MLS

Greenport Village Farmhouse Built in 2001, Featuring a New Roof (2020), a Welcoming Front Porch, and a Spacious Yard. This Three-Bedroom Home with One and Half Baths, Offers a Good-Sized Living Room and One Especially Large Bedroom with Double Closet Space. Located within One Block from a Park with Playground and a Park with Basketball Courts. A Waterfront Park and Beach is Just Eight Blocks Away and NYC Transportation is Approximately Five Blocks Away. Enjoy Easy Access to Village Shops, Restaurants, Mitchell Park Carousel, Mitchell Park Marina and So Much More from Your Comfortable Home.

416 3rd Street, Greenport

$725,000

Nestled on a generous lot in the heart of Greenport Village, this charming farmhouse offers the perfect blend of character, convenience, and potential. The location is ideal, just blocks from the beach, the Jitney, LIRR, and the vibrant shops and restaurants of the village. A classic wrap-around porch welcomes you into a sun-filled home featuring four bedrooms, two baths, village utilities and room for a pool. A great opportunity to secure a timeless village home—ready for its next chapter.

4 Beds ⋅ 2 Baths ⋅ 857635 MLS

Nestled on a generous lot in the heart of Greenport Village, this charming farmhouse offers the perfect blend of character, convenience, and potential. The location is ideal, just blocks from the beach, the Jitney, LIRR, and the vibrant shops and restaurants of the village. A classic wrap-around porch welcomes you into a sun-filled home featuring four bedrooms, two baths, village utilities and room for a pool. A great opportunity to secure a timeless village home—ready for its next chapter.

416 West Street, Greenport

$725,000

Set in the desirable Stirling Eastern Shores just minutes from the heart of Greenport Village, this 3-bedroom, 2-bath offers incredible potential in a prime coastal setting. The home features a traditional single-level layout with a living room, kitchen, and dining area that invite your personal touch. Outside, a spacious backyard, with room for pool, and private patio provide the perfect canvas for outdoor living; think garden parties, fire pit gatherings, or simply soaking in the sunshine. Best of all - just a short stroll from your front door enjoy easy access to the private Stirling Eastern Shores beach or the iconic 67 Steps Beach, both offering wide open water views and amazing sunsets. Close to wineries, farm stands, restaurants, and all the charm of Greenport Village.

3 Beds ⋅ 2 Baths ⋅ 845624 MLS

Set in the desirable Stirling Eastern Shores just minutes from the heart of Greenport Village, this 3-bedroom, 2-bath offers incredible potential in a prime coastal setting. The home features a traditional single-level layout with a living room, kitchen, and dining area that invite your personal touch. Outside, a spacious backyard, with room for pool, and private patio provide the perfect canvas for outdoor living; think garden parties, fire pit gatherings, or simply soaking in the sunshine. Best of all - just a short stroll from your front door enjoy easy access to the private Stirling Eastern Shores beach or the iconic 67 Steps Beach, both offering wide open water views and amazing sunsets. Close to wineries, farm stands, restaurants, and all the charm of Greenport Village.

750 Tasker Lane, Greenport

$690,000

(Home address on google maps and GPS know as 817 Flint Street) Don't miss out on a chance to own a home on Long Island's North Fork. This home is nested close to Greenport Village, this two story home features 3 bedrooms, 2 baths, eat in kitchen, wood finished floors through out the house. Close to shops, restaurants, transportation, schools and beaches. Sale is "AS IS" Don't miss a chance in owning your home in the North Fork area. No Showing. Drive-by-only. Please do not disturb tenants.

3 Beds ⋅ 2 Baths ⋅ 828349 MLS

(Home address on google maps and GPS know as 817 Flint Street) Don't miss out on a chance to own a home on Long Island's North Fork. This home is nested close to Greenport Village, this two story home features 3 bedrooms, 2 baths, eat in kitchen, wood finished floors through out the house. Close to shops, restaurants, transportation, schools and beaches. Sale is "AS IS" Don't miss a chance in owning your home in the North Fork area. No Showing. Drive-by-only. Please do not disturb tenants.

110 Flint Street, Greenport

$675,000

Discover the rare opportunity to own a cleared 1.48-acre flag lot, ideally situated 331 feet off the Main Road, offering ultimate privacy while remaining close to everything the North Fork has to offer. This set-back parcel is enveloped by preserved land, creating a serene and secluded setting for your future home. With the potential to accommodate a 4,000+ square foot residence, complete with a pool and additional structures such as a barn/artist studio, pool house, or garage, this property offers exceptional flexibility for your vision. Utilities abut the property, streamlining the building process. Enjoy the best of both worlds—peaceful privacy and prime proximity—just minutes from Greenport Village, renowned beaches, and celebrated vineyards. Whether you’re planning a year-round estate or a luxurious weekend getaway, this is a canvas ready for your custom build. Don’t miss this unique opportunity to create your dream home in one of the North Fork’s most desirable locations.

863312 MLS

Discover the rare opportunity to own a cleared 1.48-acre flag lot, ideally situated 331 feet off the Main Road, offering ultimate privacy while remaining close to everything the North Fork has to offer. This set-back parcel is enveloped by preserved land, creating a serene and secluded setting for your future home. With the potential to accommodate a 4,000+ square foot residence, complete with a pool and additional structures such as a barn/artist studio, pool house, or garage, this property offers exceptional flexibility for your vision. Utilities abut the property, streamlining the building process. Enjoy the best of both worlds—peaceful privacy and prime proximity—just minutes from Greenport Village, renowned beaches, and celebrated vineyards. Whether you’re planning a year-round estate or a luxurious weekend getaway, this is a canvas ready for your custom build. Don’t miss this unique opportunity to create your dream home in one of the North Fork’s most desirable locations.

2365 Main Road, Greenport

$675,000

Opportunity to invest in and restore a Greenport Village oldie. This circa 1910 Farmhouse, situated on a .17-acre lot will require a complete and comprehensive renovation. Nestled on a quiet street, this location allows for the tranquility of village life while being just two blocks from Greenport's vibrant downtown and its lively waterfront. Property is being sold “as is”.

2 Beds ⋅ 2 Baths ⋅ 896689 MLS

Opportunity to invest in and restore a Greenport Village oldie. This circa 1910 Farmhouse, situated on a .17-acre lot will require a complete and comprehensive renovation. Nestled on a quiet street, this location allows for the tranquility of village life while being just two blocks from Greenport's vibrant downtown and its lively waterfront. Property is being sold “as is”.

330 2nd Street, Greenport

$654,000

Condo in Cliffside Sound Front Complex Featuring Sound Beach, Heated Gunite Pool & Beautiful Sound Views. Easy Access to the Pool and Wow Those Spectacular Sunsets. Complex is closed Jan 15-Mar 15. Cliffside is a full resort facility.

2 Beds ⋅ 2 Baths ⋅ 996367 MLS

Condo in Cliffside Sound Front Complex Featuring Sound Beach, Heated Gunite Pool & Beautiful Sound Views. Easy Access to the Pool and Wow Those Spectacular Sunsets. Complex is closed Jan 15-Mar 15. Cliffside is a full resort facility.

61475 Route 48 Unit #A105, Greenport

$645,000

Opportunity knocks! This rare farmhouse style cottage rests on an expansive double lot on the edge of Greenport Village and is prime to be revamped. Featuring 1700sqft of interior space, a large block foundation with full basement throughout most of the footprint, a 12x22 detached garage and a yard that will allow your imagination to run wild. Walk into town, walk to 5th and 6th street beaches and easy access to all that the North Fork has to offer.

5 Beds ⋅ 2 Baths ⋅ 992307 MLS

Opportunity knocks! This rare farmhouse style cottage rests on an expansive double lot on the edge of Greenport Village and is prime to be revamped. Featuring 1700sqft of interior space, a large block foundation with full basement throughout most of the footprint, a 12x22 detached garage and a yard that will allow your imagination to run wild. Walk into town, walk to 5th and 6th street beaches and easy access to all that the North Fork has to offer.

135 Corwin Street, Greenport

$640,000

Home Sweet Home! Discover the Comfort of One-Floor Living in this Neat and Tidy Well-Maintained Home. With a New Roof and a Lovely Yard, this Home is as Functional as it is Inviting. Ideally Situated near Shops, Restaurants, and Transportation, You Are Just Moments Away from All the Places You Want to Be. With Three Bedrooms, This Home is Ideal for Convenient and Comfortable Living.

3 Beds ⋅ 1 Baths ⋅ 805847 MLS

Home Sweet Home! Discover the Comfort of One-Floor Living in this Neat and Tidy Well-Maintained Home. With a New Roof and a Lovely Yard, this Home is as Functional as it is Inviting. Ideally Situated near Shops, Restaurants, and Transportation, You Are Just Moments Away from All the Places You Want to Be. With Three Bedrooms, This Home is Ideal for Convenient and Comfortable Living.

411 2nd Street, Greenport

$630,000

Traditional Cape Cod style home ready for your magic touch. Home features hardwood floors throughout, 2 bedrooms, 1.5 baths, bonus room, fireplace, large eat-in kitchen, spacious bedrooms and plenty of room for outdoor activities- situated in a quiet neighborhood moments from Greenport Village- shopping, restaurants and wineries. Street gas accessible.

2 Beds ⋅ 2 Baths ⋅ 873224 MLS

Traditional Cape Cod style home ready for your magic touch. Home features hardwood floors throughout, 2 bedrooms, 1.5 baths, bonus room, fireplace, large eat-in kitchen, spacious bedrooms and plenty of room for outdoor activities- situated in a quiet neighborhood moments from Greenport Village- shopping, restaurants and wineries. Street gas accessible.

1295 Washington Avenue, Greenport

$605,000

Welcome to 415 Sterling Place in charming Greenport—a property brimming with potential and possibilities! This 1-bedroom, 1.5-bath home greets you with an open floor plan, soaring ceilings, and the timeless beauty of original hardwood floors. A cozy den/office provides flexibility for remote work, hobbies, or even a guest space. Step outside, and you'll discover a 1 story utility building that offers exciting opportunities—it’s ready to be transformed into a one-bedroom apartment, perfect for a mother-daughter setup, a guest suite for your overflow, or as a Southold Town affordable year round rental unit. The options are endless! Nestled in the heart of Greenport, this property is more than just a home—it’s a chance to create the lifestyle you’ve been dreaming of. Whether you’re looking to settle into a quaint retreat near the water or invest in a property with potential for growth, 415 Sterling Place checks all the boxes. Don’t miss the opportunity to make it yours!

1 Beds ⋅ 2 Baths ⋅ 972269 MLS

Welcome to 415 Sterling Place in charming Greenport—a property brimming with potential and possibilities! This 1-bedroom, 1.5-bath home greets you with an open floor plan, soaring ceilings, and the timeless beauty of original hardwood floors. A cozy den/office provides flexibility for remote work, hobbies, or even a guest space. Step outside, and you'll discover a 1 story utility building that offers exciting opportunities—it’s ready to be transformed into a one-bedroom apartment, perfect for a mother-daughter setup, a guest suite for your overflow, or as a Southold Town affordable year round rental unit. The options are endless! Nestled in the heart of Greenport, this property is more than just a home—it’s a chance to create the lifestyle you’ve been dreaming of. Whether you’re looking to settle into a quaint retreat near the water or invest in a property with potential for growth, 415 Sterling Place checks all the boxes. Don’t miss the opportunity to make it yours!

415 Sterling Place, Greenport

$595,000

Welcome to 73175 Main Road, Greenport. Fully renovated and will instantly make you feel at home. The house features three generously-sized bedrooms and two well-appointed bathrooms, providing ample space for relaxation and privacy. The thoughtful design and layout ensure a seamless flow from one room to the next, creating a sense of harmony and unity throughout the property. Room for a pool. One of the standout features of this property is its limited business zoning. This unique attribute opens up a world of opportunities for those who wish to run a business from home or explore other commercial ventures. Step outside and find yourself in the heart of Greenport, a vibrant community known for its rich history, cultural diversity, and friendly locals. The area offers a wide range of amenities, from trendy cafes and gourmet restaurants to boutique shops and outdoor recreational facilities. Whether you prefer a quiet stroll along the picturesque streets or a lively night out, Greenport has something to offer everyone. Come and experience the charm and potential of this gem for yourself. This could be the perfect place to start your next chapter!

3 Beds ⋅ 2 Baths ⋅ 910480 MLS

Welcome to 73175 Main Road, Greenport. Fully renovated and will instantly make you feel at home. The house features three generously-sized bedrooms and two well-appointed bathrooms, providing ample space for relaxation and privacy. The thoughtful design and layout ensure a seamless flow from one room to the next, creating a sense of harmony and unity throughout the property. Room for a pool. One of the standout features of this property is its limited business zoning. This unique attribute opens up a world of opportunities for those who wish to run a business from home or explore other commercial ventures. Step outside and find yourself in the heart of Greenport, a vibrant community known for its rich history, cultural diversity, and friendly locals. The area offers a wide range of amenities, from trendy cafes and gourmet restaurants to boutique shops and outdoor recreational facilities. Whether you prefer a quiet stroll along the picturesque streets or a lively night out, Greenport has something to offer everyone. Come and experience the charm and potential of this gem for yourself. This could be the perfect place to start your next chapter!

73175 Main Road, Greenport

$585,000

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.

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

$585,000

This 3-bedroom, 1-bath home is well built with a functional layout, ample light, and hardwood floors throughout—making it a great opportunity for someone looking to put their own touches on a solid home with plenty of potential. The main level features an open living area, eat-in kitchen, bright sunroom, and a first-floor bedroom, with two large, bright bedrooms upstairs. A full basement and detached garage provide additional storage or workspace. Located close to all the amenities and attractions of Greenport, this home offers convenience and flexibility in a desirable setting.

3 Beds ⋅ 1 Baths ⋅ 935401 MLS

This 3-bedroom, 1-bath home is well built with a functional layout, ample light, and hardwood floors throughout—making it a great opportunity for someone looking to put their own touches on a solid home with plenty of potential. The main level features an open living area, eat-in kitchen, bright sunroom, and a first-floor bedroom, with two large, bright bedrooms upstairs. A full basement and detached garage provide additional storage or workspace. Located close to all the amenities and attractions of Greenport, this home offers convenience and flexibility in a desirable setting.

57 (aka 400) Wilmarth Avenue, Greenport

$560,000

Prime Vacant Land in Eastern Shores Association - Build your dream home in the sought-after Eastern Shores Association community, where members enjoy exclusive access to a stunning, private Long Island Sound beach. This vacant parcel offers the perfect opportunity to create your own slice of paradise on the North Fork. Located just moments from a picturesque waterfront vineyard and winery, golf course, and the vibrant shops and restaurants of Greenport Village, this property blends natural beauty with convenient access to the area's best amenities. Don’t miss this chance to design and build your ideal coastal retreat in one of the North Fork’s most desirable communities!

866836 MLS

Prime Vacant Land in Eastern Shores Association - Build your dream home in the sought-after Eastern Shores Association community, where members enjoy exclusive access to a stunning, private Long Island Sound beach. This vacant parcel offers the perfect opportunity to create your own slice of paradise on the North Fork. Located just moments from a picturesque waterfront vineyard and winery, golf course, and the vibrant shops and restaurants of Greenport Village, this property blends natural beauty with convenient access to the area's best amenities. Don’t miss this chance to design and build your ideal coastal retreat in one of the North Fork’s most desirable communities!

1760 McCann Lane, Greenport

$560,000

Don't miss your opportunity to build your very own custom home in Greenport's Eastern Shores! 1050 Tasker Lane is located on the Northside of town situated between Inlet Pond and the adored Kontokosta Winery. This parcel being offered is level throughout, partially wooded, on a quiet street ways away from any traffic noise with soothing sounds off the beach and walking distance to famed 67 Step Beach of Greenport. 1050 Tasker Lane is an ideal piece of property for most anyone to not only dream up your Northfork getaway but to make your real estate goals a reality! There has been no preliminary work fulfilled with Dept of Health, with the Town Planning Board or Building Dept at this time.

849087 MLS

Don't miss your opportunity to build your very own custom home in Greenport's Eastern Shores! 1050 Tasker Lane is located on the Northside of town situated between Inlet Pond and the adored Kontokosta Winery. This parcel being offered is level throughout, partially wooded, on a quiet street ways away from any traffic noise with soothing sounds off the beach and walking distance to famed 67 Step Beach of Greenport. 1050 Tasker Lane is an ideal piece of property for most anyone to not only dream up your Northfork getaway but to make your real estate goals a reality! There has been no preliminary work fulfilled with Dept of Health, with the Town Planning Board or Building Dept at this time.

1050 Tasker Lane, Greenport

$523,000

Discover this rarely available Pheasant Run Condo in Greenport. This desirable 2-bedroom, 2-bath, single-level condo features a bright eat in kitchen, a spacious living room with sliders opening to a private deck, and a full basement offering abundant storage. Features include a primary bedroom with an en suite bath, in addition to a comfortable guest bedroom and full guest bath. Ideally situated just steps from the community Clubhouse and pool, the condo also offers easy access to Greenport Village, beautiful beaches, local vineyards, and convenient transportation options. With low taxes and affordable monthly maintenance, this is an exceptional opportunity to own in one of Greenport’s most sought after condo communities.

2 Beds ⋅ 2 Baths ⋅ 995502 MLS

Discover this rarely available Pheasant Run Condo in Greenport. This desirable 2-bedroom, 2-bath, single-level condo features a bright eat in kitchen, a spacious living room with sliders opening to a private deck, and a full basement offering abundant storage. Features include a primary bedroom with an en suite bath, in addition to a comfortable guest bedroom and full guest bath. Ideally situated just steps from the community Clubhouse and pool, the condo also offers easy access to Greenport Village, beautiful beaches, local vineyards, and convenient transportation options. With low taxes and affordable monthly maintenance, this is an exceptional opportunity to own in one of Greenport’s most sought after condo communities.

1565 Calebs Way Unit #D15, Greenport