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$2,400,000
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
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
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
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
$1,579,000
3 Beds ⋅ 2 Baths ⋅ 1008089 MLS
A Turn of the century well preserved 3 BR 2 Bath period home in the sought after Greenport Village. A spacious parcel with a two car garage, a secluded peaceful garden, work shed and a large private rear deck. The interior features include a formal dining room, a large kitchen with cathedral ceilings, a newly renovated bath, original pine flooring, and a delightful sun room, plus the classic front porch. All In close proximity to the Village beaches, Peconic Bay and transportation to NYC. This property is ready to welcome the next resident.

311 5th Street, Greenport
$1,500,000
4 Beds ⋅ 3 Baths ⋅ 990436 MLS
Newly Reduced Price! Welcome to 145 Osprey Nest Road, a gem nestled in the heart of the charming Cleaves Point Beach Community. This home, with its resort-like atmosphere, offers an enticing blend of comfort and convenience. As a member of the Community, this property affords use of a private Bay Beach, in addition to having a community marina with some private docks and mooring lots, in a protected inlet off the Peconic Bay. This spacious home boasts four bedrooms and three bathrooms, designed with a modern aesthetic and an open, airy layout. The primary suite offers a private retreat, while three additional guest bedrooms share a full bath. The home's generous windows and soaring ceiling heights invite an abundance of natural light, creating a warm and inviting atmosphere. The home's living spaces are equally impressive. A cozy family room, a formal living room, and a dining area that flows into an eat-in kitchen, provide ample space for entertaining or relaxing. A wood-burning fireplace adds a touch of rustic charm, and a conveniently located full bath off the kitchen houses a washer/dryer for easy laundry days. The property's exterior is equally impressive. It sits on a generous 1/3 acre corner lot, surrounded by mature hedges for added privacy. The large mahogany deck, with a built-in Endless Pool Swim Spa, is the perfect place to relax and soak in the sun. Before returning indoors, the adjacent outdoor shower is available for your use. Just a stone's throw away, you'll find the bustling Village of Greenport, home to boutique shops, top-rated restaurants, and the Greenport marina in Mitchell Park. The nearby Island’s End Golf & Country Club, vineyards, farms, and beaches, along with the Orient Beach State Park, offer a plethora of leisure activities. 145 Osprey Nest Road is more than just a home; it's a lifestyle. Experience the best of coastal living in a community that welcomes everyone. Don't miss out on this opportunity. Schedule your viewing today!

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

175 AKA 611 Maple Street, Greenport
$1,095,000
3 Beds ⋅ 2 Baths ⋅ 1021578 MLS
Charming 1920's farmhouse located in the heart of Greenport Village. Three blocks from Jitney/LIRR, restaurants, shops, galleries and Greenport's historic waterfront. 3 beds, 2 full baths, wide plank hardwood floors, updated kitchen, plumbing and electric. Attractive backyard with southern exposure. Ready to move right in and enjoy all Greenport and the North Fork has to offer. Close to town, beach and public transport.

217 Center Street, Greenport
$935,000
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
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
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
$599,000
2 Beds ⋅ 2 Baths ⋅ 1038348 MLS
Welcome to easy North Fork living in Pheasant Run. This spacious 2-bedroom, 2-bath condominium offers a comfortable single-level layout with vaulted ceilings and abundant natural light. The home features a bright kitchen with ample cabinetry, a dining area with built-in window seating, and a generous living room with direct access to the rear deck and lawn. The primary bedroom includes a private full bath, while a second bedroom and full bath provide flexibility for guests or a home office. A full basement offers substantial storage and additional possibilities. Enjoy central air, a private outdoor space, and the ease of condominium living, all just minutes from Greenport Village, beaches, wineries, restaurants, shopping, and everything the North Fork has to offer.

1235 Calebs Way Unit #G25, Greenport
$559,000
1 Beds ⋅ 1 Baths ⋅ 969086 MLS
This can be your piece of paradise on the East End of Long Island - Welcome to 31 Sage Boulevard! This one-of-a-kind, exquisite and picturesque gated community consists of 89 prime acres surrounded by the waters of the Little Peconic Bay. Upon entering the community, it will bring you back to the historical dwelling of beach cottages that have their own private beach, marina and club house. The Breezy Shores beachfront community is a co-op consisting of 31 individual and unique dwellings some of which have been modernized and expanded upon. Upon entering the front door of 31 Sage Boulevard you enter a versatile room that has plenty of space to be used as a bedroom to include a queen size bed. The dwelling has a full bathroom, a galley kitchen, ample storage and an outside shower. From all rooms in the house you have unobstructed views of the bay. While sitting in the yard, capture the beautiful setting, sea breezes and the scenic arena that a small bayfront community has to offer. The property is within close proximity to both Southold and Greenport Villages, LIRR, Vineyards and exceptional beaches. The property is in a seasonal community open from April 1 through November 1. A piece of paradise awaits you here at 31 Sage Boulevard for the Summer of 2026!

31 Sage Boulevard Unit #31, Greenport
$295,000
1 Beds ⋅ 1 Baths ⋅ 1026077 MLS
Enjoy easy living in this 1-bedroom, 1-bath co-op, located just a short walk from the charming Village of Greenport. This move-in-ready home features a newly updated kitchen with modern appliances, a renovated bathroom, and fresh finishes throughout. Perfectly situated to enjoy everything the North Fork has to offer, you'll be just minutes from beautiful beaches, award winning wineries, boutique shopping, restaurants and waterfront attractions.

1000 9th Street Unit #43, Greenport

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.