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One of Greenport’s most iconic homes, the William Corey House was built circa 1882 and stands as a beautiful testament to the village’s rich maritime history. Built for William D. Corey of Webb & Corey, a prominent ship chandlery that supplied vessels passing through Greenport’s bustling harbor, this distinguished residence has a direct connection to the working waterfront that helped shape the village. Set on a generous double lot graced by magnificent mature beech trees and a charming carriage house, the residence is distinguished by its slate roof, scalloped shingles, and decorative brackets. A gracious wraparound porch framed by Ionic columns welcomes visitors, while a Colonial-style doorway with an arched transom and sidelights adds to its timeless appeal. Together, these beautifully preserved period details reflect the craftsmanship and prosperity of Greenport’s years as a thriving port. Long admired by residents and visitors alike, 440 1st Street represents a rare opportunity to own a meaningful piece of Greenport’s architectural and maritime heritage. Awaiting its next steward, this extraordinary property offers the chance to restore its beauty, honor its history, and write the next chapter of one of the village’s most recognizable homes.

5 Beds ⋅ 2 Baths ⋅ 1056150 MLS

One of Greenport’s most iconic homes, the William Corey House was built circa 1882 and stands as a beautiful testament to the village’s rich maritime history. Built for William D. Corey of Webb & Corey, a prominent ship chandlery that supplied vessels passing through Greenport’s bustling harbor, this distinguished residence has a direct connection to the working waterfront that helped shape the village. Set on a generous double lot graced by magnificent mature beech trees and a charming carriage house, the residence is distinguished by its slate roof, scalloped shingles, and decorative brackets. A gracious wraparound porch framed by Ionic columns welcomes visitors, while a Colonial-style doorway with an arched transom and sidelights adds to its timeless appeal. Together, these beautifully preserved period details reflect the craftsmanship and prosperity of Greenport’s years as a thriving port. Long admired by residents and visitors alike, 440 1st Street represents a rare opportunity to own a meaningful piece of Greenport’s architectural and maritime heritage. Awaiting its next steward, this extraordinary property offers the chance to restore its beauty, honor its history, and write the next chapter of one of the village’s most recognizable homes.

440 1st Street, Greenport

$1,100,000

What caught my attention at 216 Monsell Place is how much of the original Greenport farmhouse feeling is still here, but the house has evolved into a layout that works really well today. You start with that wide wraparound porch. I can immediately picture sitting out there with coffee in the morning or having a drink at the end of the day. Then you walk inside and the pine floors, wood-burning fireplace and natural character remind you why these older North Fork homes are so appealing in the first place. The kitchen feels fresh and updated with new appliances, but what I really noticed was the light. There is a full-glass door at the side entrance, and in the afternoon the sunlight comes right into the kitchen. It gives the room a completely different feel and connects it visually with the backyard. Upstairs, there are three bedrooms, and one of them has some really interesting ceiling details that you just don't expect until you walk into the room. There are built-in closets, a second full bathroom, and another bright space with a great group of windows that I immediately thought would make an awesome home office. Then you walk outside and realize just how much yard there is. For Greenport Village, this is a really generous lot. You already have established trees and a great storage barn, but there is still plenty of space to have some fun with it. I can picture outdoor dining, gardens, a fire pit, lounge areas or simply a big backyard where everyone can spread out. And I like where it sits in the Village. Grab a bike and you can head over to Klipp's Park Beach, Smugglers Cove or Billy's By The Bay and spend an afternoon around the water and the marinas. For me, that's what makes this house interesting. A lot of the charm is already here, but there are still enough possibilities that you can start imagining what you would do with it.

3 Beds ⋅ 2 Baths ⋅ 1040671 MLS

What caught my attention at 216 Monsell Place is how much of the original Greenport farmhouse feeling is still here, but the house has evolved into a layout that works really well today. You start with that wide wraparound porch. I can immediately picture sitting out there with coffee in the morning or having a drink at the end of the day. Then you walk inside and the pine floors, wood-burning fireplace and natural character remind you why these older North Fork homes are so appealing in the first place. The kitchen feels fresh and updated with new appliances, but what I really noticed was the light. There is a full-glass door at the side entrance, and in the afternoon the sunlight comes right into the kitchen. It gives the room a completely different feel and connects it visually with the backyard. Upstairs, there are three bedrooms, and one of them has some really interesting ceiling details that you just don't expect until you walk into the room. There are built-in closets, a second full bathroom, and another bright space with a great group of windows that I immediately thought would make an awesome home office. Then you walk outside and realize just how much yard there is. For Greenport Village, this is a really generous lot. You already have established trees and a great storage barn, but there is still plenty of space to have some fun with it. I can picture outdoor dining, gardens, a fire pit, lounge areas or simply a big backyard where everyone can spread out. And I like where it sits in the Village. Grab a bike and you can head over to Klipp's Park Beach, Smugglers Cove or Billy's By The Bay and spend an afternoon around the water and the marinas. For me, that's what makes this house interesting. A lot of the charm is already here, but there are still enough possibilities that you can start imagining what you would do with it.

216 Monsell Place, Greenport

$1,300,000

Welcome to 402 5th Street, a 4 bedroom, 2 full bathroom historic Victorian located in the heart of west Dublin on a double lot, with plenty of room for an in-ground pool and just 3 blocks to a sandy bay beach. The home is also zoned to be converted to a 2-family dwelling. The residence offers original wide plank flooring, a large back deck and private back yard with a large shed. On the first floor, a side entrance leads to a formal kitchen, dining room, den or reading area and living room with a colossal fireplace. The second floor primary bedroom has a cathedral ceiling with skylights and plentiful amounts of natural light. There are three additional bedrooms, a full bathroom and separate exterior staircase leading to the second floor. The home is located a few blocks from the heart of Greenport Village.

4 Beds ⋅ 2 Baths ⋅ 1058255 MLS

Welcome to 402 5th Street, a 4 bedroom, 2 full bathroom historic Victorian located in the heart of west Dublin on a double lot, with plenty of room for an in-ground pool and just 3 blocks to a sandy bay beach. The home is also zoned to be converted to a 2-family dwelling. The residence offers original wide plank flooring, a large back deck and private back yard with a large shed. On the first floor, a side entrance leads to a formal kitchen, dining room, den or reading area and living room with a colossal fireplace. The second floor primary bedroom has a cathedral ceiling with skylights and plentiful amounts of natural light. There are three additional bedrooms, a full bathroom and separate exterior staircase leading to the second floor. The home is located a few blocks from the heart of Greenport Village.

402 5th Street, Greenport

$5,350,000

Perfectly positioned on a bluff overlooking the Long Island Sound, this Nantucket-style cedar-shingled home captures sweeping water views and spectacular sunsets from nearly every vantage point. Multiple waterside decks and balconies make the most of the setting, while a heated pool, outdoor kitchen, and stairs to a private beach create an exceptional environment for summer living and entertaining. Inside, beautifully appointed living spaces include en-suite bedrooms on both the first and second floors, offering flexibility for owners and guests alike. A separate waterside office with balcony round out the second floor. A finished lower level with a private theater provides additional space for recreation. Less than a mile from the heart of Greenport Village, this exceptional waterfront property combines coastal beauty, privacy, and proximity to one of the North Fork’s most desirable destinations.

5 Beds ⋅ 5 Baths ⋅ 1059750 MLS

Perfectly positioned on a bluff overlooking the Long Island Sound, this Nantucket-style cedar-shingled home captures sweeping water views and spectacular sunsets from nearly every vantage point. Multiple waterside decks and balconies make the most of the setting, while a heated pool, outdoor kitchen, and stairs to a private beach create an exceptional environment for summer living and entertaining. Inside, beautifully appointed living spaces include en-suite bedrooms on both the first and second floors, offering flexibility for owners and guests alike. A separate waterside office with balcony round out the second floor. A finished lower level with a private theater provides additional space for recreation. Less than a mile from the heart of Greenport Village, this exceptional waterfront property combines coastal beauty, privacy, and proximity to one of the North Fork’s most desirable destinations.

1000 Sound Drive, Greenport

$840,000

Beautifully renovated historic building in the heart of Greenport Village’s commercial district. This light-filled, two-story property has been home to the well-established VSOP Projects art gallery for the past eight years and offers a versatile layout well-suited to a range of uses, presenting an exciting opportunity for its next entrepreneur or investor. Stunning original wide-plank floors and a large whimsical rear garden pair seamlessly with a full slate of recent upgrades, including new electrical, HVAC, windows, insulation, siding, and lighting, creating a truly turn-key space. Ideally situated just one block from the Jitney, LIRR, Shelter Island Ferry, multiple hotels, and municipal parking, and surrounded by Greenport’s vibrant shops, restaurants, and waterfront.

1060295 MLS

Beautifully renovated historic building in the heart of Greenport Village’s commercial district. This light-filled, two-story property has been home to the well-established VSOP Projects art gallery for the past eight years and offers a versatile layout well-suited to a range of uses, presenting an exciting opportunity for its next entrepreneur or investor. Stunning original wide-plank floors and a large whimsical rear garden pair seamlessly with a full slate of recent upgrades, including new electrical, HVAC, windows, insulation, siding, and lighting, creating a truly turn-key space. Ideally situated just one block from the Jitney, LIRR, Shelter Island Ferry, multiple hotels, and municipal parking, and surrounded by Greenport’s vibrant shops, restaurants, and waterfront.

311 Front Street, Greenport

$2,795,000

Home Complete! Exceptional New Construction by well-known local builder set on .42 acres with approximately 4,600 sq. ft., offering 7 bedrooms and 6.5 baths. Sophisticated design features include 10’ ceilings, 4” white oak floors, European windows, Cortizo doors, architectural roof, and Hardie Plank siding. Designer kitchen with Tajah quartz countertops, waterfall island, custom cabinetry, butler’s pantry, Thermador appliances, XO hood and wine refrigerator. Luxurious first-floor junior en suite and stunning second-floor primary suite with spa-like wet room, soaking tub, walk-in closet and mahogany balcony. Finished lower level, gas fireplace, heated 18’ x 36’ in-ground pool, irrigation and professional landscaping. Detached two-car garage with overhead storage. A new construction offering space, style and sought after amenities. Close to 67 Steps Beach and moments from all that Greenport has to offer.

7 Beds ⋅ 7 Baths ⋅ 1053367 MLS

Home Complete! Exceptional New Construction by well-known local builder set on .42 acres with approximately 4,600 sq. ft., offering 7 bedrooms and 6.5 baths. Sophisticated design features include 10’ ceilings, 4” white oak floors, European windows, Cortizo doors, architectural roof, and Hardie Plank siding. Designer kitchen with Tajah quartz countertops, waterfall island, custom cabinetry, butler’s pantry, Thermador appliances, XO hood and wine refrigerator. Luxurious first-floor junior en suite and stunning second-floor primary suite with spa-like wet room, soaking tub, walk-in closet and mahogany balcony. Finished lower level, gas fireplace, heated 18’ x 36’ in-ground pool, irrigation and professional landscaping. Detached two-car garage with overhead storage. A new construction offering space, style and sought after amenities. Close to 67 Steps Beach and moments from all that Greenport has to offer.

1050 Tasker Lane, Greenport

$550,000

Discover the perfect opportunity to build your dream home on this beautiful 1.67-acre waterview lot in the heart of Greenport. Just five blocks from Greenport Village, you’ll have easy access to charming boutiques, renowned restaurants, lively bars, and more—all while enjoying the tranquility of your own private retreat. This property includes deeded bay beach rights at the end of 9th Street, where you can , take a refreshing swim, or set off on a peaceful kayak adventure around Pipes Cove. Please note: Showings are by appointment only. No one is permitted to walk the grounds without an agent present. Don’t miss this rare chance to own a prime piece of North Fork paradise! No one is permitted to walk the property without an appointment and must sign a Hold Harmless.

1055380 MLS

Discover the perfect opportunity to build your dream home on this beautiful 1.67-acre waterview lot in the heart of Greenport. Just five blocks from Greenport Village, you’ll have easy access to charming boutiques, renowned restaurants, lively bars, and more—all while enjoying the tranquility of your own private retreat. This property includes deeded bay beach rights at the end of 9th Street, where you can , take a refreshing swim, or set off on a peaceful kayak adventure around Pipes Cove. Please note: Showings are by appointment only. No one is permitted to walk the grounds without an agent present. Don’t miss this rare chance to own a prime piece of North Fork paradise! No one is permitted to walk the property without an appointment and must sign a Hold Harmless.

1080 9th Street, Greenport

$525,000

Greenport Village fringe vacant building lot with active setpic and building permit. Approved plans are for an approximate 2,650 sqft of living space, 3 bedrooms and 3.5 bathrooms. Close proximity to 6th St Beach, Greenport Village shopping district, local restaurant, farm-stands and vineyards. Great shovel ready opportunity!

1052155 MLS

Greenport Village fringe vacant building lot with active setpic and building permit. Approved plans are for an approximate 2,650 sqft of living space, 3 bedrooms and 3.5 bathrooms. Close proximity to 6th St Beach, Greenport Village shopping district, local restaurant, farm-stands and vineyards. Great shovel ready opportunity!

820 Wiggins Street, Greenport

$925,000

What surprised me is the option to consider a 2.7% assumable mortgage, a ownership member of the 2.5 acre beach and an updated home with updates and charm. The first thing I noticed about this house was actually the side entrance. There’s this casual mudroom entry with pieces of driftwood collected from the beach tucked around the railings, and it immediately gives the house that relaxed coastal cottage feeling. Inside, the morning light is probably one of my favorite things. The corner dining nook has windows on both sides, so the sunlight just pours into the room. From there, everything connects. The dining area opens visually to the kitchen, where the sink sits under a window looking out toward the outdoor dining table, and the living room is right there too. You can literally be cooking, sitting at the table or relaxing on the sofa and still see the TV. It’s a really comfortable layout for everyday living. The two bedrooms are nicely separated into the sleeping side of the house with the full bathroom nearby. The larger bedroom easily accommodates a king size bed, and the second works perfectly with a queen, so it feels much more like a year round home than just a little summer cottage. But the backyard might be where I would spend most of my time. A deck runs along the length of the house with room for outdoor dining and seating, then there’s another spot with double lounge chairs where you could disappear with a book or just sit there and do absolutely nothing, which honestly sounds pretty good. At night, string lights run through the trees and completely change the atmosphere around the fire pit, with seating for six or more. Between the established plantings, mature trees and detached two-car garage, the backyard feels private, comfortable and finished. Then you discover Conkling Point Beach. The association provides access to this beautiful 2.5 acre crescent shaped sandbar just a few doors away. It has sandy beach, open water views toward The Pridwin and Sunset Beach on Shelter Island, and some incredible spots to settle in with your beach chairs beneath the windswept trees. With the breeze coming off the water and the sun dropping across the horizon, it can honestly feel like you found your own little island. What makes the location work so well is that you get that quiet beach community atmosphere without feeling removed from everything. Greenport Village is about a 10 minute drive away, while Goldsmith’s Marina and Southold Fish Market are even closer. It’s the kind of house that feels easy. Morning coffee in the sunny dining nook, dinner outside on the deck, a walk down to the beach, then back home to the fire pit under the lights.

2 Beds ⋅ 1 Baths ⋅ 1050064 MLS

What surprised me is the option to consider a 2.7% assumable mortgage, a ownership member of the 2.5 acre beach and an updated home with updates and charm. The first thing I noticed about this house was actually the side entrance. There’s this casual mudroom entry with pieces of driftwood collected from the beach tucked around the railings, and it immediately gives the house that relaxed coastal cottage feeling. Inside, the morning light is probably one of my favorite things. The corner dining nook has windows on both sides, so the sunlight just pours into the room. From there, everything connects. The dining area opens visually to the kitchen, where the sink sits under a window looking out toward the outdoor dining table, and the living room is right there too. You can literally be cooking, sitting at the table or relaxing on the sofa and still see the TV. It’s a really comfortable layout for everyday living. The two bedrooms are nicely separated into the sleeping side of the house with the full bathroom nearby. The larger bedroom easily accommodates a king size bed, and the second works perfectly with a queen, so it feels much more like a year round home than just a little summer cottage. But the backyard might be where I would spend most of my time. A deck runs along the length of the house with room for outdoor dining and seating, then there’s another spot with double lounge chairs where you could disappear with a book or just sit there and do absolutely nothing, which honestly sounds pretty good. At night, string lights run through the trees and completely change the atmosphere around the fire pit, with seating for six or more. Between the established plantings, mature trees and detached two-car garage, the backyard feels private, comfortable and finished. Then you discover Conkling Point Beach. The association provides access to this beautiful 2.5 acre crescent shaped sandbar just a few doors away. It has sandy beach, open water views toward The Pridwin and Sunset Beach on Shelter Island, and some incredible spots to settle in with your beach chairs beneath the windswept trees. With the breeze coming off the water and the sun dropping across the horizon, it can honestly feel like you found your own little island. What makes the location work so well is that you get that quiet beach community atmosphere without feeling removed from everything. Greenport Village is about a 10 minute drive away, while Goldsmith’s Marina and Southold Fish Market are even closer. It’s the kind of house that feels easy. Morning coffee in the sunny dining nook, dinner outside on the deck, a walk down to the beach, then back home to the fire pit under the lights.

738 Conklin Road, Greenport

$699,000

Tucked away on one of the most coveted streets in Greenport Village, 216 Broad Street is a classic two-bedroom farmhouse just waiting for its next chapter to begin. If you’ve been dreaming of a creative project where you can build equity and put your personal stamp on a piece of North Fork history, this is the "diamond in the rough" you’ve been searching for. Stepping inside, you’re greeted by the warmth of original wood floors and the kind of architectural character that simply can't be replicated in new builds. The layout feels cozy yet functional, featuring a large pantry that offers incredible potential for a custom culinary space. Out front, the adorable porch is the perfect spot to sit with a morning coffee and soak in the breeze, while the expansive, private backyard serves as your own secret garden. The property even includes an accessory building—a blank canvas waiting for your imagination to turn it into a studio, workshop, or a unique garden retreat. Opportunities like this in the heart of Greenport are few and far between, so don't let this one slip away.

2 Beds ⋅ 1 Baths ⋅ 1047466 MLS

Tucked away on one of the most coveted streets in Greenport Village, 216 Broad Street is a classic two-bedroom farmhouse just waiting for its next chapter to begin. If you’ve been dreaming of a creative project where you can build equity and put your personal stamp on a piece of North Fork history, this is the "diamond in the rough" you’ve been searching for. Stepping inside, you’re greeted by the warmth of original wood floors and the kind of architectural character that simply can't be replicated in new builds. The layout feels cozy yet functional, featuring a large pantry that offers incredible potential for a custom culinary space. Out front, the adorable porch is the perfect spot to sit with a morning coffee and soak in the breeze, while the expansive, private backyard serves as your own secret garden. The property even includes an accessory building—a blank canvas waiting for your imagination to turn it into a studio, workshop, or a unique garden retreat. Opportunities like this in the heart of Greenport are few and far between, so don't let this one slip away.

216 Broad Street, Greenport

$864,200

Built in 1910, this classic Greenport Village farmhouse offers something that is becoming increasingly hard to find in the Village by having an extra wide, extra deep lot with the space to truly create the backyard lifestyle you have been wanting. With an outdoor fireplace under the stars, long summer dinners, gardens, entertaining space, and afternoons spent soaking up the sun before heading down to 6th Street Beach at the end of the road to cool off with the breeze off the water. Inside, the home retains original woodwork and that inviting farmhouse feel. With a surprisingly adaptable floor plan this house has an open layout. The front living room flows through the dining room and into the large farmhouse kitchen, creating a direct sightline all the way to the backyard. Morning light fills the kitchen, which opens naturally to the outdoor space and makes the yard a great space for outdoor dinners after having lunch at the beach. A generously sized bedroom on the main floor is in demand, while the second level offers an excellent opportunity to create a modern primary en-suite. That adaptability is one of the property's strongest features. Many homes from the early 1900s have floor plans that can be difficult to rework, but this home offers a layout and lot size that provide far more freedom to personalize and improve. Then there is the location. From here, Greenport Village is yours to enjoy, with easy access to the movie theater, IGA, restaurants, shops, Mitchell Park and Marina, the waterfront, and the energy that makes this Village such a special place. For someone who appreciates original character but wants the opportunity to create a home around today's lifestyle, this is an exciting chance to reimagine a classic Greenport farmhouse and make it entirely your own.

3 Beds ⋅ 2 Baths ⋅ 1041851 MLS

Built in 1910, this classic Greenport Village farmhouse offers something that is becoming increasingly hard to find in the Village by having an extra wide, extra deep lot with the space to truly create the backyard lifestyle you have been wanting. With an outdoor fireplace under the stars, long summer dinners, gardens, entertaining space, and afternoons spent soaking up the sun before heading down to 6th Street Beach at the end of the road to cool off with the breeze off the water. Inside, the home retains original woodwork and that inviting farmhouse feel. With a surprisingly adaptable floor plan this house has an open layout. The front living room flows through the dining room and into the large farmhouse kitchen, creating a direct sightline all the way to the backyard. Morning light fills the kitchen, which opens naturally to the outdoor space and makes the yard a great space for outdoor dinners after having lunch at the beach. A generously sized bedroom on the main floor is in demand, while the second level offers an excellent opportunity to create a modern primary en-suite. That adaptability is one of the property's strongest features. Many homes from the early 1900s have floor plans that can be difficult to rework, but this home offers a layout and lot size that provide far more freedom to personalize and improve. Then there is the location. From here, Greenport Village is yours to enjoy, with easy access to the movie theater, IGA, restaurants, shops, Mitchell Park and Marina, the waterfront, and the energy that makes this Village such a special place. For someone who appreciates original character but wants the opportunity to create a home around today's lifestyle, this is an exciting chance to reimagine a classic Greenport farmhouse and make it entirely your own.

410 6th Street, Greenport

$1,495,000

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.

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

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.

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

$1,175,000

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.

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

$775,000

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.

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

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 façade, 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 equipped with electricity and water, and one including a bedroom — offer flexible space for guests, 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.

2 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 façade, 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 equipped with electricity and water, and one including a bedroom — offer flexible space for guests, 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

$2,950,000

Greenport's premier Front Street address. High-visibility mixed-use building featuring in-place income and 2,912 square feet available for immediate use. Positioned on the village's busiest corridor with constant foot traffic from tourists, boaters, and ferry passengers. Existing cash flow with clear upside in the North Fork's most sought-after retail location.

989877 MLS

Greenport's premier Front Street address. High-visibility mixed-use building featuring in-place income and 2,912 square feet available for immediate use. Positioned on the village's busiest corridor with constant foot traffic from tourists, boaters, and ferry passengers. Existing cash flow with clear upside in the North Fork's most sought-after retail location.

38-44 Front Street, Greenport

$1,800,000

2.03 acres of prime real estate on route 25 in Greenport. Property is currently improved with a 1 story, 2 bedroom house and is zoned for Light Industrial. LOW yearly taxes. Schedule your showing now!

1008060 MLS

2.03 acres of prime real estate on route 25 in Greenport. Property is currently improved with a 1 story, 2 bedroom house and is zoned for Light Industrial. LOW yearly taxes. Schedule your showing now!

69430 Main Road, Greenport

$795,000

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.

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

$749,000

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.

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

$5,695,000

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.

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

1100 (aka 702 Linnett) 7th Street, Greenport

$899,000

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.

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 (aka 702 Linnett) 7th Street, Greenport

$2,399,000

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

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

$1,276,000

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.

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

$1,799,000

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.

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

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.

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

$1,595,000

A rare and exceptional offering in the heart of Greenport—one of the only duplex-style properties of its kind on the North Fork—this fully turnkey property delivers a unique combination of lifestyle, flexibility, and proven income potential. Located within Greenport Village and offering approximately 3,376 square feet of living space, this back-to-back duplex features two fully independent, two-story residences, each with its own full basement, central air conditioning, and private living areas as well as two electric panels, two meters, two propane tanks and separate basements. Built approximately 7 years ago, the property offers the advantages of newer construction, including modern systems, efficient design, and low-maintenance living. The front residence offers 4 bedrooms and 2.5 baths, highlighted by a welcoming covered front porch, fireplace, and a full basement with 8-foot ceilings—ideal for expansion, recreation, or storage. The rear residence features 3 bedrooms and 2.5 baths, a gas fireplace, and a full walk-out basement, providing excellent privacy and functionality. Outdoor features include a spacious back deck, side yard with a fire pit and a large yard, offering ample room for entertaining or relaxation. Being sold fully furnished and turnkey, the property is ready for immediate use. With a proven history of generating approximately $125,000 annually, this property presents a compelling opportunity for both end-users and investors. Ideally situated within walking distance to the vibrant village center, the Greenport Free Library, and public transportation, the property provides easy access to waterfront dining, marinas, shops, and all that the North Fork has to offer. This is more than a home—it’s a rare opportunity to own a flexible, income-producing property in one of the North Fork’s most sought-after locations.

7 Beds ⋅ 6 Baths ⋅ 982976 MLS

A rare and exceptional offering in the heart of Greenport—one of the only duplex-style properties of its kind on the North Fork—this fully turnkey property delivers a unique combination of lifestyle, flexibility, and proven income potential. Located within Greenport Village and offering approximately 3,376 square feet of living space, this back-to-back duplex features two fully independent, two-story residences, each with its own full basement, central air conditioning, and private living areas as well as two electric panels, two meters, two propane tanks and separate basements. Built approximately 7 years ago, the property offers the advantages of newer construction, including modern systems, efficient design, and low-maintenance living. The front residence offers 4 bedrooms and 2.5 baths, highlighted by a welcoming covered front porch, fireplace, and a full basement with 8-foot ceilings—ideal for expansion, recreation, or storage. The rear residence features 3 bedrooms and 2.5 baths, a gas fireplace, and a full walk-out basement, providing excellent privacy and functionality. Outdoor features include a spacious back deck, side yard with a fire pit and a large yard, offering ample room for entertaining or relaxation. Being sold fully furnished and turnkey, the property is ready for immediate use. With a proven history of generating approximately $125,000 annually, this property presents a compelling opportunity for both end-users and investors. Ideally situated within walking distance to the vibrant village center, the Greenport Free Library, and public transportation, the property provides easy access to waterfront dining, marinas, shops, and all that the North Fork has to offer. This is more than a home—it’s a rare opportunity to own a flexible, income-producing property in one of the North Fork’s most sought-after locations.

213-215 North Street, Greenport

$1,297,000

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.

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

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.

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

$485,000

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!!

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

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