Greenport, NY Homes for Sale

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  /39

  $1,500,000

  $150K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,528 Sq Ft

  145 Osprey Nest Rd, Greenport, NY 11944

  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

  

  Richard Connelly

  Douglas Elliman Real Estate

  (833) 464-0605

  145 Osprey Nest Rd, Greenport, NY 11944
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  /10

  $725,000

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft

  27 (AKA 630) Madison St, Greenport, NY 11944

  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. The home currently has tenants, who will be leaving.

  

  Frank Mistretta

  Daniel Gale Sothebys Intl Rlty

  (844) 931-0450

  27 (AKA 630) Madison St, Greenport, NY 11944
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  /14

  $549,000

  • Land
  • 23,958 Sq Ft
  • $998,182 per Acre

  110 Homestead Way, Greenport, NY 11944

  Build Your Dream Home In The Bucolic Area Of Eastern Shores. More Than A Half Acre Wooded Lot Available To Suit Your Wants And Needs. This Land Is In The Eastern Shores Association Community, Where Members Enjoy Exclusive Access To a Stunning, Private Long Island Sound Beach All For a Small Monthly Fee. Close To Water, Beaches, Wineries, Golf, Greenport Village Loaded With Shops, Restaurants, And

  

  Lisa Urcuiolio

  Century 21 Crown Homes

  (833) 615-1638

  110 Homestead Way, Greenport, NY 11944
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  /39

  $1,149,900

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  380 Homestead Way, Greenport, NY 11944

  Welcome to this beautifully appointed single-family residence ideally situated just minutes from the charming village of Greenport. Blending modern amenities with classic coastal charm, this property offers not only an exceptional retreat in one of Long Island’s most sought-after locations—but also a compelling opportunity as a fully functional or potential income-producing short-term rental.

  Jules Zaphire Locqube New York, Inc.

  380 Homestead Way, Greenport, NY 11944
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  /32

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 2,012 Sq Ft

  55 Brown St, Greenport, NY 11944

  Experience the pinnacle of refined living in this completely reimagined home, boasting a comprehensive renovation and redesign led by a professional interior designer. Every square inch has been thoughtfully curated, starting with the custom front door featuring openable screened sidelights that welcome you inside.Premium oak hardwood flooring flows seamlessly throughout the main living

  JoAnn Wind Daniel Gale Sothebys Intl Rlty

  55 Brown St, Greenport, NY 11944
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  /40

  $2,650,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  56765 Route 48, Greenport, NY 11944

  Beautiful, expansive soundfront retreat offering rare, direct waterfront access with no bluff and sweeping 180-degree panoramic views. Set on .75 acres, this exceptional 3-bedroom, 2-bath home features a waterside gunite pool perfectly positioned to capture breathtaking sunsets over the Sound. The interior showcases modern finishes and an open-concept layout designed for effortless indoor-outdoor

  Kris Pilles East End Luxury Ltd

  56765 Route 48, Greenport, NY 11944
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  /28

  $2,350,000

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  172 5th St, Greenport, NY 11944

  Available furnished, this recently renovated Greenport Village house in prized West Dublin neighborhood – one block to three beaches and just short walk to town and the jitney! Meticulously restored with historic charm which seamlessly blends into a large thoughtful addition.9+ feet high ceilings on the first floor with original base, crown and molding details. The front living room leads to

  Justin Concannon Compass Greater NY LLC

  172 5th St, Greenport, NY 11944
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  /49

  $1,297,000

  • 4 Beds
  • 2 Baths
  • 1,784 Sq Ft

  407 Wiggins St, Greenport, NY 11944

  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

  Douglas Cabral Century 21 Excelsior Realty

  407 Wiggins St, Greenport, NY 11944
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  /24

  $1,459,000

  • 3 Beds
  • 2 Baths
  • 1,671 Sq Ft

  412 Atlantic Ave, Greenport, NY 11944

  Water view meticulously renovated 3 bedroom 2-bath corner home in Greenport, offering privacy with a landscaped fenced-in garden. A true sanctuary, a large side open spacious garden with mature trees and an intimate private patio that overlooks the picturesque Sterling Harbor, alive with sailboats and fishing vessels.This thoughtfully renovated home has been thoroughly rebuilt, showcasing its

  Paul Betancourt Engel & Volkers North Fork

  412 Atlantic Ave, Greenport, NY 11944
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  /16

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,249 Sq Ft

  1565 Calebs Way Unit D15, Greenport, NY 11944

  Discover this rarely available Pheasant Run Condo in Greenport. This desirable 2-bedroom, 2-bath, single-level condo features a bright eat in kitchen, a spacious living room with sliders opening to a private deck, and a full basement offering abundant storage. Features include a primary bedroom with an en suite bath, in addition to a comfortable guest bedroom and full guest bath. Ideally situated

  Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  1565 Calebs Way Unit D15, Greenport, NY 11944
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  /21

  $2,100,000

  • 5 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  151 Bay Ave, Greenport, NY 11944

  This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed

  Barbara Poliwoda Douglas Elliman Real Estate

  151 Bay Ave, Greenport, NY 11944
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  /23

  $1,249,000

  Open Sat 12AM - 3PM $351K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft

  336 2nd St, Greenport, NY 11944

  * low-maintenance North Fork lifestyle,* weekend retreat,* turnkey without renovation headaches,* walkability,* lock-and-leave second home,* income potential,* simpler ownership vs larger estates “Freshly repositioned for the spring market, this beautifully renovated Village home offers exceptional value and immediate enjoyment. Featuring a complete renovation including

  Ron Moschetta Keller Williams Realty Greater

  336 2nd St, Greenport, NY 11944
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  /28

  $1,170,000

  $79K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  1705 Kerwin Blvd, Greenport, NY 11944

  Opportunities like this in August Acres are few and far between. This 4-bedroom, 2.5-bath Colonial with deeded beach rights delivers the rare combination buyers wait for—location, efficiency, and long-term value—without compromise.From the moment you arrive, the home feels both welcoming and solid. A cozy fireplace anchors the main living space, while tilt-in Andersen windows fill the home

  Maureen Orientale Compass Greater NY LLC

  1705 Kerwin Blvd, Greenport, NY 11944
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  /49

  $1,899,000

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  1025 9th St, Greenport, NY 11944

  Greenport Gem - Renovated American Square. Gated and Nestled Behind Tall Hedges for Privacy on a Large Corner Lot with Room for Pool, You Will Find This Fully Restored (2012) and Gently Lived-In Stately 1930's Classic. The Original Woodwork, Doors and Flooring are Preserved Throughout the Home. Take a Step Back in Time but With All the Modern Conveniences (including Central Airconditioning).

  Paul Loeb Douglas Elliman Real Estate

  1025 9th St, Greenport, NY 11944
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  /46

  $1,675,000

  • 7 Beds
  • 6 Baths
  • 3,376 Sq Ft

  215 North St, Greenport, NY 11944

  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,

  Kim Pirreca BERKSHIRE HATHAWAY

  215 North St, Greenport, NY 11944
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  /26

  $2,100,000

  • 4 Beds
  • 2.5 Baths
  • 2,410 Sq Ft

  660 Sutton Place, Greenport, NY 11944

  Built in 2021 and offered in like-new condition, this stylish four-bedroom residence pairs clean contemporary design with the relaxed ease of North Fork living. A semi-open floor plan creates natural flow across the main level, connecting the living, dining, and kitchen spaces in a layout equally suited for everyday living and effortless entertaining. Four spacious bedrooms offer comfortable

  Bridget Elkin Compass Greater NY LLC

  660 Sutton Place, Greenport, NY 11944
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  /20

  $1,150,000

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  450 Maple Ln, Greenport, NY 11944

  Welcome to North Fork living at its finest! This beautifully maintained 3-bedroom 2 1/2-bath home offers the perfect blend ofcoastal charm and comfort, ideally located just moments from the golf course and with private beach access. Surrounded bystunning, professionally landscaped grounds, the property features an inviting deck and spacious patio-perfect for outdoorentertaining or

  Peter Johnstone Century 21 Albertson Realty

  450 Maple Ln, Greenport, NY 11944
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  /43

  $1,785,000

  • 4 Beds
  • 3 Baths
  • 3,392 Sq Ft

  90 Caiola Ct, Greenport, NY 11944

  Located in coveted Rock Cove Estates in Greenport, this beautifully maintained cedar shake and stone residence offers the perfect blend of privacy, comfort, and North Fork lifestyle. Built in 2007 and lovingly cared for by its original owner, the home features four bedrooms and three full baths, including a spacious primary suite with well-appointed bath with double sinks, Jacuzzi tub and

  Kristy Naddell Douglas Elliman Real Estate

  90 Caiola Ct, Greenport, NY 11944
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  /20

  $895,000

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  307 Champlin Place, Greenport, NY 11944

  GREENPORT, NY: Recently renovated farmhouse in a quiet neighborhood. 2 bedrooms 1 bath. Open concept, eat in kitchen, central air conditioning, washer/dryer, Gas grill, fire pit, dining /seating area, WiFi/cable. Close to downtown Greenport, beaches, wineries, and major North Fork attractions. Ready for Summer 2026! Exclusive: $895K.

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  307 Champlin Place, Greenport, NY 11944
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  /15

  $278,000

  $29K PRICE INCREASE

  • 1 Bed
  • 1 Bath

  690 Queen St Unit 4 Coastal Cottage, Greenport, NY 11944

  North Fork Resort offers a private cottage resort experience in Greenport, in the heart of North Fork wine country. This fully furnished Park Model Vacation Cottage provides a place to return to - whether for a few days, a week, or extended time throughout the season - without the burden of traditional second-home ownership. Enjoy the comfort of your own cottage with access to a full resort

  Samantha Ripka RESOURCE REALTY GROUP

  690 Queen St Unit 4 Coastal Cottage, Greenport, NY 11944
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  /17

  $1,600,000

  $150K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  240 August Ln, Greenport, NY 11944

  Greenport - Historic Colonial Farmhouse in Peconic Bay Estates.Offered for the first time in decades is this rare slice of Long Island history. Step back in time without sacrificing modern comfort in this circa 1600s, Dutch Colonial farmhouse, gracefully set on .39 acres in the heart of the North Fork. With 4-5 bedrooms, 3 full baths, and over 400 years of character, this one-of-a-kind home

  Deirdre DeVita Sothebys Int'l Realty Hamptons

  240 August Ln, Greenport, NY 11944
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  /12

  $3,495,000

  $300K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft

  438 Main St, Greenport, NY 11944

  Introducing the 1902 Merrick Hand House-an architecturally significant residence crafted by Henry Leek-set on a deep and rare .63-acre parcel in the heart of Amagansett. With its historic designation, the home's iconic front façade must be preserved, while permitted expansion and renovation provide an exceptional opportunity to blend timeless character with modern luxury. The first floor features

  Heather Saskas Compass

  438 Main St, Greenport, NY 11944
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  /11

  $1,579,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  311 5th St, Greenport, NY 11944

  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

  Paul Betancourt Engel & Volkers North Fork

  311 5th St, Greenport, NY 11944
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  /27

  $2,400,000

  $295K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,980 Sq Ft

  168 Sterling St, Greenport, NY 11944

  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

  Bridget Elkin Compass Greater NY LLC

  168 Sterling St, Greenport, NY 11944
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  /17

  $1,377,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  550 Madison Ave, Greenport, NY 11944

  Okay, so the first thing, you get out of the car and this farmhouse style has the front porch that actually has room for a side table and chair to have my morning coffee in peace that I have wanted so badly. Then inside, the half bath is right next to the front door, but it's tucked far enough away from the open living room and kitchen that it doesn't feel awkward when all of us are hanging out.

  Jerry Cibulski Century 21 Albertson Realty

  550 Madison Ave, Greenport, NY 11944
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  /32

  $1,285,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  175 AKA 611 Maple St, Greenport, NY 11944

  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

  Kristy Naddell Douglas Elliman Real Estate

  175 AKA 611 Maple St, Greenport, NY 11944
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  /12

  $549,900

  • Land
  • 11.76 Acres
  • $46,760 per Acre

  0 Middle Rd, Greenport, NY 12534

  Great parcel on a lesser traveled Road. Small stream at rear of property line. Very nice long range views. Minutes to the Hudson Train Station, NYS Thruway, Taconic Parkway, Hudson Boat Launch, Olana,, downtown Hudson, and the list goes on. Possible homesite and well are situated on a nice knoll overlooking the parcel. Parcel is lightly wooded with some open areas and maybe a potential pond view.

  Bob Kavanaugh Barns & Farms Realty, LLC

  0 Middle Rd, Greenport, NY 12534
• 

  

  /17

  $2,700,000

  • 3 Beds
  • 3 Baths
  • 1,652 Sq Ft

  100 Sound Dr, Greenport, NY 11944

  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

  Christopher Andron Andron Realty Group Tulip R E

  100 Sound Dr, Greenport, NY 11944
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  /33

  $824,990

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  275 Sound Rd, Greenport, NY 11944

  Renovated 1910 Colonial with Beautiful 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,

  Gina Walter Century 21 Cor Ace Realty Inc

  275 Sound Rd, Greenport, NY 11944
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  /29

  $1,275,000

  $100K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,400 Sq Ft

  130 Tasker Ln, Greenport, NY 11944

  Welcome to this charming cape, a true gem with its private beach and inviting swimming pool. This sweet home features 4 bedrooms and 2 full baths, combining easy living and casual comfort . Spacious, sunlit rooms provide ample living space for relaxation and entertaining. Cozy up by the fireplace in the living room, or retreat to the den for a quiet evening with a book or movie. The open-concept

  Kristen Rishe Signature Premier Properties

  130 Tasker Ln, Greenport, NY 11944
• 

  

  /18

  $1,399,000

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  321 Bridge St, Greenport, NY 11944

  Welcome to 325 Bridge Street, a beautifully renovated modern retreat nestled in the vibrant heart of Greenport, NY. This exquisite residence, set on an expansive 8,712 square foot lot, seamlessly blends elegance with modern convenience. Step inside to discover stunning new hardwood floors that flow throughout, leading you to a stylish kitchen with views of the professionally landscaped outdoor

  Jennifer Benton Compass Greater NY LLC

  321 Bridge St, Greenport, NY 11944
• 

  

  /17

  $559,000

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft

  31 Sage Blvd Unit 31, Greenport, NY 11944

  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

  William Galati Signature Premier Properties

  31 Sage Blvd Unit 31, Greenport, NY 11944
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  /41

  $1,297,000

  • 4 Beds
  • 2 Baths
  • 1,740 Sq Ft

  401 Wiggins St, Greenport, NY 11944

  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,

  Douglas Cabral Century 21 Excelsior Realty

  401 Wiggins St, Greenport, NY 11944
• 

  

  /46

  $1,499,000

  Open Sun 1PM - 2:30PM

  • 4 Beds
  • 1.5 Baths
  • 1,880 Sq Ft

  1760 Albertson Ln, Greenport, NY 11944

  Scenic and bucolic, this 3+ acre country farm is steeped in classic North Fork charm. The property features an authentic 1800s four-bedroom, one and a half bath, farmhouse, a 2+ car garage (1976) with a workshop, office and mechanics pit, and a 1985 barn equipped with three horse stalls and ample space for tractors. Additional structures include a cinderblock chicken coop and a pig sty, offering

  Paul Loeb Douglas Elliman Real Estate

  1760 Albertson Ln, Greenport, NY 11944
• 

  

  /15

  $725,000

  $74K PRICE DROP

  • 5 Beds
  • 1.5 Baths
  • 1,700 Sq Ft

  135 Corwin St, Greenport, NY 11944

  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

  William Walters Daniel Gale Sothebys Intl Rlty

  135 Corwin St, Greenport, NY 11944
• 

  

  /12

  $243,000

  $113K PRICE INCREASE

  • 1 Bed
  • 1 Bath

  690 Queen St Unit Sound Cottage, Greenport, NY 11944

  North Fork Resort offers a private cottage resort experience in Greenport, in the heart of North Fork wine country. This fully furnished Park Model Vacation Cottage provides a place to return to - whether for a few days, a week, or extended time throughout the season - without the burden of traditional second-home ownership. Enjoy the comfort of your own cottage with access to a full resort

  Samantha Ripka RESOURCE REALTY GROUP

  690 Queen St Unit Sound Cottage, Greenport, NY 11944
• 

  

  /46

  $2,799,000

  $200K PRICE DROP

  • 4 Beds
  • 3 Baths

  2100 Sound Dr, Greenport, NY 11944

  Soundfront! Welcome to 2100 Sound Drive - offering water views from nearly every room, this unique property is part of the Eastern Sterling Shores community and is truly the Last of the Mohicans! Greeted by a welcoming circular driveway and situated atop a picturesque bluff, you'll enjoy captivating views and summer breezes. Stairs lead to an enchanting enclosed bungalow while your own private

  Connie Liappas Compass Greater NY LLC

  2100 Sound Dr, Greenport, NY 11944
• 

  

  /15

  $286,950

  $157K PRICE INCREASE

  • 2 Beds
  • 1 Bath

  690 Queen St Unit Coastal Cottage, Greenport, NY 11944

  North Fork Resort offers a private cottage resort experience in Greenport, in the heart of North Fork wine country. This fully furnished Park Model Vacation Cottage provides a place to return to - whether for a few days, a week, or extended time throughout the season - without the burden of traditional second-home ownership. Enjoy the comfort of your own cottage with access to a full resort

  Samantha Ripka RESOURCE REALTY GROUP

  690 Queen St Unit Coastal Cottage, Greenport, NY 11944
• 

  

  /30

  $1,435,000

  Open Sat 12:30PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  210 5th St, Greenport, NY 11944

  This classic Greenport Village Craftsman has the kind of charm that is getting harder to find — bright, airy rooms, beautiful period detail, and an easy coastal feel just one block from the beach. Front and back porches provide multiple outdoor seating areas. Inside, the home features coffered ceilings, warm wood floors, and sun-filled living and dining spaces. Outside, the private, fully fenced

  Jill Dunbar Douglas Elliman Real Estate

  210 5th St, Greenport, NY 11944
• 

  

  /28

  $669,000

  • 2 Beds
  • 2 Baths
  • 730 Sq Ft

  61475 Route 48 Unit A105, Greenport, NY 11944

  Condo in Cliffside Sound Front Complex Featuring Sound Beach, Heated Gunite Pool & Beautiful Sound Views. This Unit has 2 Beds (Primary with Ensuite) & 2 Baths and a Waterview Covered Deck. Lower Level Large Storage Area with Sliders doubles as a Bonus Room. Easy Access to the Pool and Wow Those Spectacular Sunsets. Complex is closed Jan 15-Mar 15. Cliffside is a full resort facility. Condo has

  Paul Loeb Douglas Elliman Real Estate

  61475 Route 48 Unit A105, Greenport, NY 11944

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