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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

2 Family on Large Lot. Completely Renovated. New; Foam Insulation, Electric, Plumbing, Central AC, Gas Heating, Oak Floors Through out, New Cesspool, All Done To Code With Proper Permits. New Asphalt Driveway Lined With Belgian Block, Trex Decking, In Ground Sprinklers, & More! Ready For Delivery! Near Many Vineyards, Shelter Rock Ferry, & Public and Private Beaches!

4 Beds ⋅ 3 Baths ⋅ 962530 MLS

2 Family on Large Lot. Completely Renovated. New; Foam Insulation, Electric, Plumbing, Central AC, Gas Heating, Oak Floors Through out, New Cesspool, All Done To Code With Proper Permits. New Asphalt Driveway Lined With Belgian Block, Trex Decking, In Ground Sprinklers, & More! Ready For Delivery! Near Many Vineyards, Shelter Rock Ferry, & Public and Private Beaches!

7600 Main Road, East Marion

$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

$875,000

Spacious ranch on large level lot with beautiful mature trees located a very short distance to private association beach on Long Island Sound. Ample room for pool. Three bedrooms, two full baths, open plan kitchen to dining area with wood burning stove. Large living room, full basement, one car attached garage, mud room, hardwood floors and central air conditioning complete the package.

3 Beds ⋅ 2 Baths ⋅ 879579 MLS

Spacious ranch on large level lot with beautiful mature trees located a very short distance to private association beach on Long Island Sound. Ample room for pool. Three bedrooms, two full baths, open plan kitchen to dining area with wood burning stove. Large living room, full basement, one car attached garage, mud room, hardwood floors and central air conditioning complete the package.

2000 Greenway East E, Orient

$870,000

Village Lane charmer located a short walk to the bay and all village amenities. Gourmet kitchen, open common space, wonderfully bright and airy. Second floor master suite with window seat, bedroom, bath, sitting room, and rear balcony. Large accessory 2-story studio. Brick patio/garden connecting house and studio for outdoor dining and entertaining.

1 Beds ⋅ 2 Baths ⋅ 848840 MLS

Village Lane charmer located a short walk to the bay and all village amenities. Gourmet kitchen, open common space, wonderfully bright and airy. Second floor master suite with window seat, bedroom, bath, sitting room, and rear balcony. Large accessory 2-story studio. Brick patio/garden connecting house and studio for outdoor dining and entertaining.

1740 Village Lane, Orient

$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

2820 Shipyard Lane Unit #2C2, East Marion

$835,000

Walking into this place, I actually said “okay…this is exactly what I’ve been hunting for”. First off, it’s not just a condo, it is a complete waterfront beach resort. They have recently refreshed tennis courts tucked into these tall pine trees, so even when you’re just standing there you feel vacation vibes. Then you turn the corner and there’s the pool scene: plenty of lounge chairs so you can do the sun or shade depending on the tan line status. The gym is right next to the pool with updated equipment, and it looks out over the pool so I can actually stick to a flexible plan: quick workout, then laps, then back to the pool chair. Or I can skip all of that and go straight to the sandy beach and just wander the shoreline that even has a view toward the lighthouse out by Orient Beach State Park. Now the best part: this is a second-floor unit, which means nobody is above and that changes the whole ceiling and layout. What I really like is the commanding water view from the kitchen, living room, and deck. The living room has double-height ceilings and a fireplace, so it feels open and airy, not boxed-in—and the water views are unreal as the weather changes. The main bedroom has its own water view and with the high ceiling and the updated bathroom has fresh open feeling. The kitchen is dialed-in with views of the water—new stainless steel appliances, quartz counters and a breakfast bar that keeps everyone on the living room side. The deck is set up brilliantly: there’s an extra counter with stools along the living room wall, so you’ve got this indoor-outdoor wine-and-cheese flow that feels effortless. And somehow the deck is built so you don’t really see the neighbors—no idea how but I’m a fan. When the others come out, there’s a second floor den with water views too (because the living room ceiling is so high, it creates this cool extra space). Islands End Golf Course and the Hellenic are under a mile away, so that’s a two-minute drive. Greenport Village is only about 2.5 miles away for shops, food, and everything that I love to do on the North Fork. And then it hit me, the Shelter Island ferries are right there. That opens up Shelter Island restaurants, quick trips toward Sag Harbor. If I have to run into the city, the train and Hampton Jitney are right by the ferry terminal too, so it’s genuinely easy to come and go. This is one of those places that makes sense in every season, summer, fall, winter and the best part is when I lock the door, I am not stressing outdoor maintenance. I can just leave, head south, and actually relax. Then the new clubhouse is across the path by the gas grill patio where I can keep my own, tennis courts offer pickle ball also and the pool and decks have all new tables, chairs and umbrellas. The new gym is one of the best I have seen in the area. This is great space for summer gatherings with the new restrooms and kitchen space. They even have a huge flatscreen tv in the Clubhouse. The floating swim platform is close enough to the sandy beach and Adirondack chairs, I can see this getting lots of use. What an amazing location, feels like a vacation resort on the beach for sure. The boat docks are available so there is time to take the most of fishing by the Gut at Orient Point.

1 Beds ⋅ 2 Baths ⋅ 961692 MLS

Walking into this place, I actually said “okay…this is exactly what I’ve been hunting for”. First off, it’s not just a condo, it is a complete waterfront beach resort. They have recently refreshed tennis courts tucked into these tall pine trees, so even when you’re just standing there you feel vacation vibes. Then you turn the corner and there’s the pool scene: plenty of lounge chairs so you can do the sun or shade depending on the tan line status. The gym is right next to the pool with updated equipment, and it looks out over the pool so I can actually stick to a flexible plan: quick workout, then laps, then back to the pool chair. Or I can skip all of that and go straight to the sandy beach and just wander the shoreline that even has a view toward the lighthouse out by Orient Beach State Park. Now the best part: this is a second-floor unit, which means nobody is above and that changes the whole ceiling and layout. What I really like is the commanding water view from the kitchen, living room, and deck. The living room has double-height ceilings and a fireplace, so it feels open and airy, not boxed-in—and the water views are unreal as the weather changes. The main bedroom has its own water view and with the high ceiling and the updated bathroom has fresh open feeling. The kitchen is dialed-in with views of the water—new stainless steel appliances, quartz counters and a breakfast bar that keeps everyone on the living room side. The deck is set up brilliantly: there’s an extra counter with stools along the living room wall, so you’ve got this indoor-outdoor wine-and-cheese flow that feels effortless. And somehow the deck is built so you don’t really see the neighbors—no idea how but I’m a fan. When the others come out, there’s a second floor den with water views too (because the living room ceiling is so high, it creates this cool extra space). Islands End Golf Course and the Hellenic are under a mile away, so that’s a two-minute drive. Greenport Village is only about 2.5 miles away for shops, food, and everything that I love to do on the North Fork. And then it hit me, the Shelter Island ferries are right there. That opens up Shelter Island restaurants, quick trips toward Sag Harbor. If I have to run into the city, the train and Hampton Jitney are right by the ferry terminal too, so it’s genuinely easy to come and go. This is one of those places that makes sense in every season, summer, fall, winter and the best part is when I lock the door, I am not stressing outdoor maintenance. I can just leave, head south, and actually relax. Then the new clubhouse is across the path by the gas grill patio where I can keep my own, tennis courts offer pickle ball also and the pool and decks have all new tables, chairs and umbrellas. The new gym is one of the best I have seen in the area. This is great space for summer gatherings with the new restrooms and kitchen space. They even have a huge flatscreen tv in the Clubhouse. The floating swim platform is close enough to the sandy beach and Adirondack chairs, I can see this getting lots of use. What an amazing location, feels like a vacation resort on the beach for sure. The boat docks are available so there is time to take the most of fishing by the Gut at Orient Point.

2820 Shipyard Lane Unit #2C2, East Marion

$830,000

Welcome to this meticulously maintained Craftsman home in the heart of Orient. A home where timeless character meets modern, move-in condition. This mint condition 3 bedroom, 2 bath offers a perfect blend of classic architectural charm with bonus modern amenities. Set on a private, landscaped yard, this property offers a serene outdoor retreat. Perfect for relaxing, dining alfresco, or enjoying the peaceful surroundings. Ideally located just moments from Village Lane, pristine Bay and Sound beaches, and Orient's beloved local amenities. This home places you at the center of one of the North Fork's most desirable coastal communities. Whether you're searching fora primary residence, weekend getaway, or investment property, this exceptional Craftsman delivers on location, condition, and lifestyle.

3 Beds ⋅ 2 Baths ⋅ 988496 MLS

Welcome to this meticulously maintained Craftsman home in the heart of Orient. A home where timeless character meets modern, move-in condition. This mint condition 3 bedroom, 2 bath offers a perfect blend of classic architectural charm with bonus modern amenities. Set on a private, landscaped yard, this property offers a serene outdoor retreat. Perfect for relaxing, dining alfresco, or enjoying the peaceful surroundings. Ideally located just moments from Village Lane, pristine Bay and Sound beaches, and Orient's beloved local amenities. This home places you at the center of one of the North Fork's most desirable coastal communities. Whether you're searching fora primary residence, weekend getaway, or investment property, this exceptional Craftsman delivers on location, condition, and lifestyle.

23530 Main Road, Orient

$825,000

Charming and private home in Green Acres in Orient Point. Open floor plan with dining room/kitchen opening onto lovely second floor deck. The living room and rear deck have open views of 63 acres of pastoral undeveloped preserved land. Association sound beach down the road.

2 Beds ⋅ 2 Baths ⋅ 893595 MLS

Charming and private home in Green Acres in Orient Point. Open floor plan with dining room/kitchen opening onto lovely second floor deck. The living room and rear deck have open views of 63 acres of pastoral undeveloped preserved land. Association sound beach down the road.

685 Greenway W, Orient

$800,000

Charming Cape with a large pool, farm views, and a sandy bay beach at the end of the street. The light-filled first floor features a welcoming foyer, a spacious living room, dining room, and a generous eat-in kitchen that opens to a cozy den with a fireplace. Outdoors, the backyard is anchored by a beautiful swimming pool with southwest exposure and overlooks a picturesque farm and nursery, offering exceptional privacy and a serene North Fork setting. Three oversized bedrooms and two full baths provide ample space for hosting guests. Conveniently located just minutes from Greenport Village, Orient Village, and both the Cross Sound Ferry to Connecticut and the North Ferry to Shelter Island and Sag Harbor.

3 Beds ⋅ 2 Baths ⋅ 955966 MLS

Charming Cape with a large pool, farm views, and a sandy bay beach at the end of the street. The light-filled first floor features a welcoming foyer, a spacious living room, dining room, and a generous eat-in kitchen that opens to a cozy den with a fireplace. Outdoors, the backyard is anchored by a beautiful swimming pool with southwest exposure and overlooks a picturesque farm and nursery, offering exceptional privacy and a serene North Fork setting. Three oversized bedrooms and two full baths provide ample space for hosting guests. Conveniently located just minutes from Greenport Village, Orient Village, and both the Cross Sound Ferry to Connecticut and the North Ferry to Shelter Island and Sag Harbor.

1650 Gillette Drive, East Marion

$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

$775,000

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

3 Beds ⋅ 2 Baths ⋅ 1010914 MLS

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

275 Sound Road, Greenport

$770,000

Stunning North Fork Colonial in Orient Welcome to your dream home on the beautiful North Fork. Situated on a flat spacious acre with mature specimen trees provide privacy in the desirable community of Orient by the Sea. This post modern residence offers the perfect blend of luxury and comfort with 4 generous bedrooms, including a remarkable 3-room primary suite on the main floor featuring a private sitting room, this home is designed for relaxation and privacy. The great room boasts soaring ceilings and a striking stone fireplace with gleaming hardwood floors and walls of glass fill the living area with natural sunlight and warmth throughout the year. Entertain guests with ease on the wrap-around covered porch, ideal for gatherings and enjoying the tranquil surroundings. The kitchen offers classic wood cabinets, stainless steel appliances and quartz counters and backsplash. As part of a private deeded beach community, you are minutes away from the beach with your own private park area -- pristine beach, kayak launch, swimming, fishing, picnic, entertainment area and outdoor grill. Watch the sunset on the Long Island sound or visit North Fork wineries, world-class golf courses, charming towns and villages, country farm stands, fine dining, shopping and more. Conveniently located near the Orient Point Ferry, Orient Beach State Park and dining, entertainment and marina at Duryea’s Beach Club. Experience the best of coastal living in an area celebrated for its beauty and vibrant lifestyle.

4 Beds ⋅ 3 Baths ⋅ 947427 MLS

Stunning North Fork Colonial in Orient Welcome to your dream home on the beautiful North Fork. Situated on a flat spacious acre with mature specimen trees provide privacy in the desirable community of Orient by the Sea. This post modern residence offers the perfect blend of luxury and comfort with 4 generous bedrooms, including a remarkable 3-room primary suite on the main floor featuring a private sitting room, this home is designed for relaxation and privacy. The great room boasts soaring ceilings and a striking stone fireplace with gleaming hardwood floors and walls of glass fill the living area with natural sunlight and warmth throughout the year. Entertain guests with ease on the wrap-around covered porch, ideal for gatherings and enjoying the tranquil surroundings. The kitchen offers classic wood cabinets, stainless steel appliances and quartz counters and backsplash. As part of a private deeded beach community, you are minutes away from the beach with your own private park area -- pristine beach, kayak launch, swimming, fishing, picnic, entertainment area and outdoor grill. Watch the sunset on the Long Island sound or visit North Fork wineries, world-class golf courses, charming towns and villages, country farm stands, fine dining, shopping and more. Conveniently located near the Orient Point Ferry, Orient Beach State Park and dining, entertainment and marina at Duryea’s Beach Club. Experience the best of coastal living in an area celebrated for its beauty and vibrant lifestyle.

175 Uhl Lane, Orient

$755,000

Updated Ranch Home with 3 Bedrooms and So Much More! Very Close to a Beautiful, Scenic Long Island Sound Beach for Swimming, Fishing and Memorable Sunsets! Detached 1+ Garage. Additional Parks District Beach, Farm Stands, Golf and Greenport Village Shops and Restaurants All Nearby.

3 Beds ⋅ 1 Baths ⋅ 830215 MLS

Updated Ranch Home with 3 Bedrooms and So Much More! Very Close to a Beautiful, Scenic Long Island Sound Beach for Swimming, Fishing and Memorable Sunsets! Detached 1+ Garage. Additional Parks District Beach, Farm Stands, Golf and Greenport Village Shops and Restaurants All Nearby.

4645 Rocky Point Road, East Marion

$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

$750,000

Beautifully preserved with many original details, intact turn of the century Farmhouse set on 1/2 acres with 2 original accessory structures and mature plantings. 3 bedrooms, 1.5 baths, wrap-around porch, updated cedar shake roof, updated kitchen appliances, sunny mudroom, hard wood floors, original woodwork and moldings. Private rear yard that backs onto 36.5 acres of open space. Close to beaches, State Park, East Marion Country Store, Jitney and Greenport Village. Sound beach rights to Truman’s Beach.

3 Beds ⋅ 2 Baths ⋅ L3544978 MLS

Beautifully preserved with many original details, intact turn of the century Farmhouse set on 1/2 acres with 2 original accessory structures and mature plantings. 3 bedrooms, 1.5 baths, wrap-around porch, updated cedar shake roof, updated kitchen appliances, sunny mudroom, hard wood floors, original woodwork and moldings. Private rear yard that backs onto 36.5 acres of open space. Close to beaches, State Park, East Marion Country Store, Jitney and Greenport Village. Sound beach rights to Truman’s Beach.

12115 Main Road, East Marion

$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

$650,000

East Marion, North Fork – Classic Farmhouse with Legal Cottage & Barn, Priced to Sell! Don’t miss this rare opportunity to own a charming piece of North Fork history—just moments from Truman’s Beach and all the beloved attractions of the East End. Set on a shy acre, this character-filled property features an older, maintained farmhouse, a legal guest cottage, and a versatile two-story barn with a storied past. The main home blends vintage charm with modern updates, offering an open floor plan with a spacious living room, original wood-burning fireplace, a large country-style kitchen, mudroom, and a first-floor bedroom and full bath. Upstairs, you’ll find three additional bedrooms and a second full bath—perfect for hosting family and friends. Enjoy the comfort of natural gas heating, central air conditioning, and an updated kitchen that makes everyday living a breeze. The expansive lot includes: A two-story barn – formerly a commercial scallop shack, ready for creative repurposing (permit needed) and a LEGAL one-bedroom cottage – complete with living room, kitchen, and full bath—ideal for guests, rental income, or a private studio. The property functioned as a popular Bed & Breakfast for many years and the cottage has a rental permit making it an ideal, supplemental, income source. This is your chance to own a true North Fork retreat with space, flexibility, and timeless appeal. Act fast—this East Marion gem won’t last!

5 Beds ⋅ 3 Baths ⋅ 903269 MLS

East Marion, North Fork – Classic Farmhouse with Legal Cottage & Barn, Priced to Sell! Don’t miss this rare opportunity to own a charming piece of North Fork history—just moments from Truman’s Beach and all the beloved attractions of the East End. Set on a shy acre, this character-filled property features an older, maintained farmhouse, a legal guest cottage, and a versatile two-story barn with a storied past. The main home blends vintage charm with modern updates, offering an open floor plan with a spacious living room, original wood-burning fireplace, a large country-style kitchen, mudroom, and a first-floor bedroom and full bath. Upstairs, you’ll find three additional bedrooms and a second full bath—perfect for hosting family and friends. Enjoy the comfort of natural gas heating, central air conditioning, and an updated kitchen that makes everyday living a breeze. The expansive lot includes: A two-story barn – formerly a commercial scallop shack, ready for creative repurposing (permit needed) and a LEGAL one-bedroom cottage – complete with living room, kitchen, and full bath—ideal for guests, rental income, or a private studio. The property functioned as a popular Bed & Breakfast for many years and the cottage has a rental permit making it an ideal, supplemental, income source. This is your chance to own a true North Fork retreat with space, flexibility, and timeless appeal. Act fast—this East Marion gem won’t last!

11005 Main Road, East Marion

$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

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