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Set on one of Greenport Village's most sought-after streets, this charming cedar-shingled home offers a rare opportunity to own a waterfront Village property with a generous deep-water dock. The home features a beautifully detailed interior with updated kitchen and baths, original millwork, and a separate one-bedroom apartment. Outdoors, a waterside deck and spacious yard create an ideal setting for entertaining or quiet enjoyment, framed by open-water views. A detached garage and whole-house generator add to the home’s versatility and ease of ownership. Located just one-third of a mile from Greenport’s vibrant commercial center, restaurants, boutiques, and cafes. This property is one of only a few that pair waterfront living with effortless village access.

3 Beds ⋅ 3 Baths ⋅ 970395 MLS

Set on one of Greenport Village's most sought-after streets, this charming cedar-shingled home offers a rare opportunity to own a waterfront Village property with a generous deep-water dock. The home features a beautifully detailed interior with updated kitchen and baths, original millwork, and a separate one-bedroom apartment. Outdoors, a waterside deck and spacious yard create an ideal setting for entertaining or quiet enjoyment, framed by open-water views. A detached garage and whole-house generator add to the home’s versatility and ease of ownership. Located just one-third of a mile from Greenport’s vibrant commercial center, restaurants, boutiques, and cafes. This property is one of only a few that pair waterfront living with effortless village access.

168 Sterling Street, Greenport

$2,200,000

Immeasurable charm in the heart of Greenport Village. Beautifully updated while retaining much of its historic character, the main house features three bedrooms and three full baths, a handsome kitchen flooded with natural light, high ceilings, restored pocket doors, and original period moldings. At the rear of the property, a charming two-bedroom guest cottage with a full bath and kitchen provides wonderful flexibility for hosting or additional living and work space. Outside, the pool is tucked into beautifully established gardens, complemented by a bluestone patio and extensive mature landscaping that give the property a remarkable sense of privacy and place. All of this just moments from Greenport's downtown waterfront and some of the North Fork's best restaurants, shops, and waterfront destinations, with beaches, farm stands, and vineyards all within a mile.

5 Beds ⋅ 4 Baths ⋅ 1043780 MLS

Immeasurable charm in the heart of Greenport Village. Beautifully updated while retaining much of its historic character, the main house features three bedrooms and three full baths, a handsome kitchen flooded with natural light, high ceilings, restored pocket doors, and original period moldings. At the rear of the property, a charming two-bedroom guest cottage with a full bath and kitchen provides wonderful flexibility for hosting or additional living and work space. Outside, the pool is tucked into beautifully established gardens, complemented by a bluestone patio and extensive mature landscaping that give the property a remarkable sense of privacy and place. All of this just moments from Greenport's downtown waterfront and some of the North Fork's best restaurants, shops, and waterfront destinations, with beaches, farm stands, and vineyards all within a mile.

611 1st Street, Greenport

$1,995,000

This beautifully renovated 4 bedroom + den and office waterfront home (house is not in a flood zone) offers a seamless blend of modern comfort and timeless coastal style. Walkable to the village, beach, restaurants and jitney pick up! Inside, the expanded floor plan opens into spacious, light-filled living areas designed for both everyday living and entertaining. A first-floor ensuite bedroom adds convenience and flexibility. High ceilings and expansive windows frame the water views, filling the space with natural light. The custom chef’s kitchen features top-of-the-line appliances and flows easily into both formal and informal dining areas. The large living room includes a gas fireplace, game area, and a striking marine-lacquered wet bar complete with fridge/freezer adjacent to both pool and living areas. An additional den with water views offers a quiet retreat or extra space for guests. Outdoors, cedar fencing encloses a private backyard with a heated saltwater pool, areas for al fresco dining, and space to relax. Upstairs features two guest bedrooms sharing a well-appointed designer bath, tub shower combo. The primary suite has stunning water views, cathedral-ceiling, a separate sitting room/office, spacious dressing room, and a spa-like bath with soaking tub, large shower, and separate water closet with bidet. Stone steps lead through beach grass to a private dock—perfect for boating, kayaking, or paddle boarding. Located a few blocks outside Greenport village, yet tucked away from the crowds, and near one of the North Fork’s best bay beaches, this home offers the ideal balance of serenity and convenience. Also available furnished.

4 Beds ⋅ 4 Baths ⋅ 915982 MLS

This beautifully renovated 4 bedroom + den and office waterfront home (house is not in a flood zone) offers a seamless blend of modern comfort and timeless coastal style. Walkable to the village, beach, restaurants and jitney pick up! Inside, the expanded floor plan opens into spacious, light-filled living areas designed for both everyday living and entertaining. A first-floor ensuite bedroom adds convenience and flexibility. High ceilings and expansive windows frame the water views, filling the space with natural light. The custom chef’s kitchen features top-of-the-line appliances and flows easily into both formal and informal dining areas. The large living room includes a gas fireplace, game area, and a striking marine-lacquered wet bar complete with fridge/freezer adjacent to both pool and living areas. An additional den with water views offers a quiet retreat or extra space for guests. Outdoors, cedar fencing encloses a private backyard with a heated saltwater pool, areas for al fresco dining, and space to relax. Upstairs features two guest bedrooms sharing a well-appointed designer bath, tub shower combo. The primary suite has stunning water views, cathedral-ceiling, a separate sitting room/office, spacious dressing room, and a spa-like bath with soaking tub, large shower, and separate water closet with bidet. Stone steps lead through beach grass to a private dock—perfect for boating, kayaking, or paddle boarding. Located a few blocks outside Greenport village, yet tucked away from the crowds, and near one of the North Fork’s best bay beaches, this home offers the ideal balance of serenity and convenience. Also available furnished.

980 Manhanset Avenue, 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.

215 North Street, Greenport

$1,585,000

Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings, an elegant open staircase, and an inviting sense of scale that sets the tone for the home's thoughtfully designed interior. The main level offers an exceptional layout for both everyday living and entertaining, featuring a formal dining room, gracious living room, and an inviting media room anchored by a classic wood-burning fireplace. At the heart of the home, the spacious eat-in kitchen is appointed with abundant cabinetry, generous counter space, and a highly functional layout designed to accommodate everything from casual everyday meals to large-scale gatherings. Just beyond, a private home office overlooks the rear grounds, providing a peaceful and inspiring workspace. Occupying nearly 900 square feet, the second-floor primary suite serves as a true private retreat, complete with dual custom walk-in closets and a luxurious spa-inspired bath featuring double vanities, a walk-in shower, and a Jacuzzi soaking tub. Three additional guest bedrooms and a well-appointed full hallway bathroom complete the upper level, providing comfortable accommodations for family and guests alike. Another huge bonus is the expansive unfinished basement with 8' ceilings and walk-out egress already in place, making this ripe for another fully finished space which would add approximately 1400 additional sqft. Perfectly positioned within one of Greenport's most desirable beach communities, residents enjoy private access to the Rock Cove Estates association beach while remaining just minutes from the vibrant shops, acclaimed restaurants, marinas, and waterfront attractions of Greenport Village, as well as the renowned wineries, farm stands, and scenic beauty that define the North Fork lifestyle.

4 Beds ⋅ 3 Baths ⋅ 1027434 MLS

Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings, an elegant open staircase, and an inviting sense of scale that sets the tone for the home's thoughtfully designed interior. The main level offers an exceptional layout for both everyday living and entertaining, featuring a formal dining room, gracious living room, and an inviting media room anchored by a classic wood-burning fireplace. At the heart of the home, the spacious eat-in kitchen is appointed with abundant cabinetry, generous counter space, and a highly functional layout designed to accommodate everything from casual everyday meals to large-scale gatherings. Just beyond, a private home office overlooks the rear grounds, providing a peaceful and inspiring workspace. Occupying nearly 900 square feet, the second-floor primary suite serves as a true private retreat, complete with dual custom walk-in closets and a luxurious spa-inspired bath featuring double vanities, a walk-in shower, and a Jacuzzi soaking tub. Three additional guest bedrooms and a well-appointed full hallway bathroom complete the upper level, providing comfortable accommodations for family and guests alike. Another huge bonus is the expansive unfinished basement with 8' ceilings and walk-out egress already in place, making this ripe for another fully finished space which would add approximately 1400 additional sqft. Perfectly positioned within one of Greenport's most desirable beach communities, residents enjoy private access to the Rock Cove Estates association beach while remaining just minutes from the vibrant shops, acclaimed restaurants, marinas, and waterfront attractions of Greenport Village, as well as the renowned wineries, farm stands, and scenic beauty that define the North Fork lifestyle.

90 Caiola Court, Greenport

$1,579,000

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

3 Beds ⋅ 2 Baths ⋅ 1008089 MLS

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

311 5th Street, Greenport

$935,000

Welcome to 1175 9th Street in Greenport—a two-story, four-bedroom, three-and-a-half-bath with a full, finished basement with exterior staircase. The home is filled with natural light and hardwood floors throughout the main living spaces. The first floor offers an open living area with a wood-burning fireplace that flows into a spacious eat-in kitchen with a large island and sliding glass doors to the a secluded and private rear yard. Just off the entry, a formal dining room connects to the kitchen, and a hallway includes a conveniently placed half bath and pantry. Upstairs are four bedrooms, including a primary suite with an ensuite bath, plus a second full bathroom. In the winter months, two of the bedrooms enjoy views of the bay. The finished full basement adds flexible bonus space with a full bathroom, a dedicated laundry area with washer and dryer, and a walk-out staircase to the exterior side yard. Less than a half mile to 5th and 6th Street beach, park and dock and roughly three-quarters of a mile to the heart of Greenport Village, this location makes it easy to enjoy the waterfront and town year-round.

4 Beds ⋅ 4 Baths ⋅ 952083 MLS

Welcome to 1175 9th Street in Greenport—a two-story, four-bedroom, three-and-a-half-bath with a full, finished basement with exterior staircase. The home is filled with natural light and hardwood floors throughout the main living spaces. The first floor offers an open living area with a wood-burning fireplace that flows into a spacious eat-in kitchen with a large island and sliding glass doors to the a secluded and private rear yard. Just off the entry, a formal dining room connects to the kitchen, and a hallway includes a conveniently placed half bath and pantry. Upstairs are four bedrooms, including a primary suite with an ensuite bath, plus a second full bathroom. In the winter months, two of the bedrooms enjoy views of the bay. The finished full basement adds flexible bonus space with a full bathroom, a dedicated laundry area with washer and dryer, and a walk-out staircase to the exterior side yard. Less than a half mile to 5th and 6th Street beach, park and dock and roughly three-quarters of a mile to the heart of Greenport Village, this location makes it easy to enjoy the waterfront and town year-round.

1175 9th Street, Greenport

$799,900

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

$725,000

This charming cape is situated in Greenport, just minutes from Greenport Village and Beaches. The home has 4 bedrooms, 2 full bathrooms, and approximately 1500 sq ft. The eat-in kitchen has granite countertops and an awesome backsplash. The basement is unfinished with bilco doors. There is a fenced backyard and 1 car garage.

4 Beds ⋅ 2 Baths ⋅ 999238 MLS

This charming cape is situated in Greenport, just minutes from Greenport Village and Beaches. The home has 4 bedrooms, 2 full bathrooms, and approximately 1500 sq ft. The eat-in kitchen has granite countertops and an awesome backsplash. The basement is unfinished with bilco doors. There is a fenced backyard and 1 car garage.

27 (AKA 630) Madison Street, Greenport

$559,000

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

1 Beds ⋅ 1 Baths ⋅ 969086 MLS

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

31 Sage Boulevard Unit #31, Greenport

$500,000

Build your dream home near the beach! This .24 acre parcel offers a great opportunity to create your own retreat, just 3 miles from town. Enjoy deeded beach rights and the convenience of being close to local shops, dining and amenities, while still enjoying a private setting. A rare opportunity to own land with beach access—bring your vision and make it your own!

1047008 MLS

Build your dream home near the beach! This .24 acre parcel offers a great opportunity to create your own retreat, just 3 miles from town. Enjoy deeded beach rights and the convenience of being close to local shops, dining and amenities, while still enjoying a private setting. A rare opportunity to own land with beach access—bring your vision and make it your own!

1400 Bay Shore Road, Greenport

$295,000

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

1 Beds ⋅ 1 Baths ⋅ 1026077 MLS

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

1000 9th Street Unit #43, Greenport