2,662

Greenport, NY Homes

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  • /39

    $1,500,000

    $150K PRICE DROP Pending
    • 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

    Agent Photo

    Richard Connelly

    Douglas Elliman Real Estate

    145 Osprey Nest Rd, Greenport, NY 11944
  • /28

    $12,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • House for Rent

    312 5th Ave, Greenport, NY 11944

    2026 Rates: April $7,500; May $12K; June $15K; July $25K; A1-LD $27,500; Sept $12,500; October $10K: This beautifully curated home away from home, blends modern design with warmth and style. Experience elegant comfort in your private retreat with natural light, modern decor and thoughtful touches throughout. Nestled on a quiet, tree lined street, this special haven features a front porch, fully

    William Walters Daniel Gale Sothebys Intl Rlty

    312 5th Ave, Greenport, NY 11944
  • 55 Brown St, Greenport, NY 11944

    $1,294,000

    Sold Sep 25, 2026

    55 Brown St, Greenport, NY 11944

    • 3 Beds
    • 3 Baths
    • 2,012 Sq Ft
    • Built 2006

    Last Sold Summary

    • 7% Below List Price
    • $643/SF
    • 197 Days On Market

    Current Estimated Value $1,310,704

    Last Listing Agent JoAnn Wind Daniel Gale Sothebys Intl Rlty

    55 Brown St, Greenport, NY 11944
    • 61475 County Road 48, Greenport, NY 11944

      Not Listed For Sale

      61475 County Road 48, Greenport, NY 11944

      • 2 Beds
      • 2 Baths
      • 730 Sq Ft
      • Built 2008
      61475 County Road 48, Greenport, NY 11944

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Jill Dunbar Douglas Elliman Real Estate

  • /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
  • /37

    $12,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    185 Inlet Ln, Greenport, NY 11944

    August still available! Summer on the North Fork starts here. Welcome to 185 Inlet Lane, Greenport, a spacious 6-bedroom, 4.5-bath coastal retreat designed for entertaining and relaxing near the beach. Perfectly situated a block from sandy Norman Klipp Beach, this home offers casual beach living and effortless entertaining. Inside, there's room for everyone with expansive living and gathering

    Melissa Principi Douglas Elliman Real Estate

    185 Inlet Ln, Greenport, NY 11944
  • 35 Washington Ave, Greenport, NY 11944

    $750,000

    Sold Apr 30, 2026

    35 Washington Ave, Greenport, NY 11944

    • 5 Beds
    • 3 Baths
    • 1,805 Sq Ft
    • Built 1928

    Last Sold Summary

    • 14% Below List Price
    • $416/SF
    • 99 Days On Market

    Current Estimated Value $792,277

    Last Listing Agent Kathleen Coughlan Coldwell Banker American Homes

    35 Washington Ave, Greenport, NY 11944
    • 3080 Bay Shore Rd, Greenport, NY 11944

      Est $1,457,591

      Not Listed For Sale

      3080 Bay Shore Rd, Greenport, NY 11944

      • 3 Beds
      • 2 Baths
      • 2,200 Sq Ft
      • Built 2020
      3080 Bay Shore Rd, Greenport, NY 11944

      Last Sold Summary

      • 112 Days On Market

      Last Listing Agent Maureen Orientale Compass Greater NY LLC

  • /38

    $1,585,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,392 Sq Ft

    90 Caiola Ct, Greenport, NY 11944

    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,

    William Walters Daniel Gale Sothebys Intl Rlty

    90 Caiola Ct, Greenport, NY 11944
  • /23

    $3,500 Per Month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    424 4th St, Greenport, NY 11944

    Welcome to your very own pied-a-terre cottage nestled on the world renowned grounds of Harbor Knoll guesthouse. Bask in this waterfront, private and secluded oasis of calm, while still being within arms reach of everything Greenport Village has to offer. This quaint cottage boasts, hardwood floors, ductless air-conditioning, an eat in kitchen, primary suite and a pullout sofa bed in the living

    Peter Halpin Douglas Elliman Real Estate

    424 4th St, Greenport, NY 11944
  • 2365 Main Rd, Greenport, NY 11944

    $675,000

    Sold Feb 24, 2026

    2365 Main Rd, Greenport, NY 11944

    • Land
    • 1.48 Acres
    • $456,081 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 229 Days On Market

    Last Listing Agent William Walters Daniel Gale Sothebys Intl Rlty

    2365 Main Rd, Greenport, NY 11944
    • 890 Westwood Ln, Greenport, NY 11944

      Est $680,862

      Not Listed For Sale

      890 Westwood Ln, Greenport, NY 11944

      890 Westwood Ln, Greenport, NY 11944

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Gayle Marriner Smith Daniel Gale Sothebys Intl Rlty

  • /23

    $1,100,000

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

    435 Sound Rd, Greenport, NY 11944

    What stands out about this home is how established and inviting it already feels. Mature trees and thoughtful landscaping surround the property, creating a beautiful setting from the moment you arrive. The covered front porch is a perfect place to sit and take in the changing colors of spring and summer, including the striking blue blossoms of the mature Vitex that become a highlight of the

    Jerry Cibulski Century 21 Albertson Realty

    435 Sound Rd, Greenport, NY 11944
  • /32

    $14,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,452 Sq Ft
    • House for Rent

    237 6th St, Greenport, NY 11944

    Beautifully Renovated Greenport Village Farmhouse with Bay Beaches, NYC Transportation, Village Shops and A Marina Nearby. Summer 2026 - July $14,000; August to Labor Day $17,500. Permit#25-018.

    Paul Loeb Douglas Elliman Real Estate

    237 6th St, Greenport, NY 11944
  • 58315 North Rd, Greenport, NY 11944

    $992,000

    Sold Dec 12, 2025

    58315 North Rd, Greenport, NY 11944

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Below List Price
    • $1,102/SF
    • 0 Days On Market

    Current Estimated Value $1,003,247

    Last Listing Agent Donna Fakiris Modern Age Realty Group LLC

    58315 North Rd, Greenport, NY 11944
    • 190 Fiddler Ln, Greenport, NY 11944

      Est $1,351,753

      Not Listed For Sale

      190 Fiddler Ln, Greenport, NY 11944

      • 4 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2018
      190 Fiddler Ln, Greenport, NY 11944

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Melissa Principi Douglas Elliman Real Estate

  • /17

    $925,000

    • 2 Beds
    • 1 Bath
    • 925 Sq Ft

    738 Conklin Rd, Greenport, NY 11944

    The first thing I noticed about this house was actually the side entrance. There’s this casual mudroom entry with pieces of driftwood collected from the beach tucked around the railings, and it immediately gives the house that relaxed coastal cottage feeling.Inside, the morning light is probably one of my favorite things. The corner dining nook has windows on both sides, so the sunlight just

    Jerry Cibulski Century 21 Albertson Realty

    738 Conklin Rd, Greenport, NY 11944
  • /8

    $2,650 Per Month

    • 4 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • House for Rent

    317 South St, Greenport, NY 11944

    Discover your perfect winter retreat at 317 South Street, Greenport. This delightful 4-bedroom, 1.5-bathroom home blends timeless charm with modern comfort, making it an ideal seasonal escape for the colder months. The main level is designed for easy living, highlighting a formal dining room for hosting and a bright sunroom that brings in plenty of natural light. The kitchen comes fully equipped

    Jennifer Benton Compass Greater NY LLC

    317 South St, Greenport, NY 11944
  • 131 6th St Unit 7, Greenport, NY 11944

    $1,687,500

    Sold Nov 03, 2025

    131 6th St Unit 7, Greenport, NY 11944

    • 3 Beds
    • 2.5 Baths
    • 2,238 Sq Ft
    • Built 1990

    Last Sold Summary

    • 15% Below List Price
    • $754/SF
    • 144 Days On Market

    Last Listing Agent Sheri Winter Parker Corcoran

    131 6th St Unit 7, Greenport, NY 11944
    • 230 Wiggins Ln, Greenport, NY 11944

      Est $1,049,826

      Not Listed For Sale

      230 Wiggins Ln, Greenport, NY 11944

      230 Wiggins Ln, Greenport, NY 11944

      Last Sold Summary

      • 297 Days On Market

      Last Listing Agent Paul Loeb Douglas Elliman Real Estate

  • /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
  • /30

    $38,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,700 Sq Ft
    • House for Rent

    1000 Sound Dr, Greenport, NY 11944

    Immaculate shingle-style home perched above the Long Island Sound. Enjoy endless water views and breathtaking sunsets from the heated pool and private beach. Open floor plan with EIK and fireplace, bedrooms across three floors, including first and second-floor primary suites with private waterside balconies. The large finished basement features a media/game room. The private office is ideal for

    Eric Elkin Compass Greater NY LLC

    1000 Sound Dr, Greenport, NY 11944
  • 506 5th St, Greenport, NY 11944

    $940,000

    Sold Jun 16, 2026

    506 5th St, Greenport, NY 11944

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • Built 1868

    Last Sold Summary

    • 18% Below List Price
    • $522/SF
    • 103 Days On Market

    Current Estimated Value $1,076,966

    Last Listing Agent Mariah Mills Daniel Gale Sothebys Intl Rlty

    506 5th St, Greenport, NY 11944
    • 43 Sound Rd, Greenport, NY 11944

      Est $801,565

      Not Listed For Sale

      43 Sound Rd, Greenport, NY 11944

      • 2 Beds
      • 2 Baths
      • 1,215 Sq Ft
      • Built 1956
      43 Sound Rd, Greenport, NY 11944

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Paul Loeb Douglas Elliman Real Estate

  • /10

    $775,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,200 Sq Ft

    429 Kaplan Ave, Greenport, NY 11944

    Charming Greenport Village GetawayEnjoy the best of the North Fork from this inviting 3-bedroom, 2-bath home, perfectly located near all that Greenport Village has to offer. Stroll to Mitchell Park, waterfront dining, restaurants, shops, and the Shelter Island Ferry, or spend the day exploring nearby vineyards and Greenport Harbor Brewing Company.A wonderful opportunity to enjoy

    Mary Terry MCKENNASHEA LLC

    429 Kaplan Ave, Greenport, NY 11944
  • /16

    $18,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • House for Rent

    134 6th St, Greenport, NY 11944

    Charming whole-house rental in Greenport Village’s coveted West Dublin neighborhood, with a classic bay beach just at the end of the block. The home features lovely furnishings, quality linens, and abundant natural light throughout. A large, sunny backyard offers ample space for outdoor dining and summer gatherings. Located just half a mile from Greenport’s vibrant commercial district, you’ll

    Bridget Elkin Compass Greater NY LLC

    134 6th St, Greenport, NY 11944
  • 57 (aka 400) Wilmarth Ave, Greenport, NY 11944

    $585,000

    Sold Feb 26, 2026

    57 (aka 400) Wilmarth Ave, Greenport, NY 11944

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Built 1953

    Last Sold Summary

    • $390/SF
    • 104 Days On Market

    Last Listing Agent Marc Rishe Century 21 Albertson Realty

    57 (aka 400) Wilmarth Ave, Greenport, NY 11944
    • 16 Washington Ave, Greenport, NY 11944

      Est $898,414

      Not Listed For Sale

      16 Washington Ave, Greenport, NY 11944

      • 3 Beds
      • 1.5 Baths
      • 1,550 Sq Ft
      • Built 1920
      16 Washington Ave, Greenport, NY 11944

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Bridget Elkin Compass Greater NY LLC

  • /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
  • /18

    $16,000 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft
    • House for Rent

    446 6th St, Greenport, NY 11944

    Charming Greenport Village renovated 1935 Sears Kit House offering 3 bedrooms and 1.5 bathrooms. Ideally located less than half a mile from Greenport’s vibrant downtown, and less than half a mile from 5th Street Beach. The home features a bright and inviting living area, updated kitchen and dining space, and home office. Enjoy a peaceful, private backyard retreat complete with a relaxing hot tub

    Bridget Elkin Compass Greater NY LLC

    446 6th St, Greenport, NY 11944
  • 1565 Calebs Way Unit D15, Greenport, NY 11944

    $523,000

    Sold Sep 11, 2026

    1565 Calebs Way Unit D15, Greenport, NY 11944

    • 2 Beds
    • 2 Baths
    • 1,249 Sq Ft
    • Built 1996

    Last Sold Summary

    • 5% Below List Price
    • $419/SF
    • 40 Days On Market

    Current Estimated Value $549,683

    Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

    1565 Calebs Way Unit D15, Greenport, NY 11944
    • 49 Sound Rd, Greenport, NY 11944

      Not Listed For Sale

      49 Sound Rd, Greenport, NY 11944

      • 2 Beds
      • 1 Bath
      • 965 Sq Ft
      • Built 1970
      49 Sound Rd, Greenport, NY 11944

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Cindy Succoso Douglas Elliman Real Estate

  • /23

    $999,750

    Open House 10/10 $600K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    336 2nd St, Greenport, NY 11944

    BRING ALL OFFERSGREENPORT, NY — RELAUNCHED UNDER $1 MILLIONLimited supply. Strong demand. Location, location, location.Real estate values have always been influenced by location, supply and demand—and Greenport continues to attract buyers looking for the unique lifestyle of the North Fork.Now is the time to take another look at 336 2nd Street, newly offered at

    Ron Moschetta Keller Williams Realty Greater

    336 2nd St, Greenport, NY 11944
  • /15

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft
    • Condo for Rent

    8 Oyster Point, Greenport, NY 11944

    GREENPORT WATERFRONT CONDO . Enjoy your life in this well- appointed Bayfront 2 bedroom, 2 bath condo with stunning views of Shelter Island and Greenport Harbor. Amenities include a waterfront pool, tennis & pickle ball court, 200 Ft of private sandy bay beach, and your own boat slip in the private marina. Located just a short distance to shops and restaurants in Historic Greenport Village, ferry

    Jeanmarie Bay William Raveis New York LLC

    8 Oyster Point, Greenport, NY 11944
  • 3200 Sound Dr, Greenport, NY 11944

    $2,142,500

    Sold May 27, 2026

    3200 Sound Dr, Greenport, NY 11944

    • 4 Beds
    • 3 Baths
    • 3,145 Sq Ft
    • Built 1996

    Last Sold Summary

    • 9% Below List Price
    • $681/SF
    • 60 Days On Market

    Current Estimated Value $2,209,967

    Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

    3200 Sound Dr, Greenport, NY 11944
  • /19

    $599,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,180 Sq Ft

    1235 Calebs Way Unit G25, Greenport, NY 11944

    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

    Thomas McCarthy Thomas J McCarthy Real Estate

    1235 Calebs Way Unit G25, Greenport, NY 11944
  • /21

    $15,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft
    • House for Rent

    242 Maple Ln, Greenport, NY 11944

    Brand-new, beautifully designed home with an in-ground pool and finished basement. This exceptional lease opportunity, set within a private beach community, offers a newly constructed four-bedroom, three-and-a-half-bath home designed for effortless coastal living. Bright interiors flow through a sophisticated chef’s kitchen with ample cabinetry, stainless steel appliances, and a generous eat-in

    Diane Mollica Compass Greater NY LLC

    242 Maple Ln, Greenport, NY 11944
  • 1111 Main St, Greenport, NY 11944

    $1,200,000

    Sold Dec 05, 2025

    1111 Main St, Greenport, NY 11944

    • 3 Beds
    • 2 Baths
    • 2,363 Sq Ft
    • Built 1956

    Last Sold Summary

    • 8% Below List Price
    • $508/SF
    • 77 Days On Market

    Current Estimated Value $1,197,705

    Last Listing Agent Jon Tomlinson Daniel Gale Sothebys Intl Rlty

    1111 Main St, Greenport, NY 11944
    • 365 Island View Ln, Greenport, NY 11944

      Est $1,512,695

      Not Listed For Sale

      365 Island View Ln, Greenport, NY 11944

      • 3 Beds
      • 1 Bath
      • 1,386 Sq Ft
      • Built 1960
      365 Island View Ln, Greenport, NY 11944

      Last Sold Summary

      • 140 Days On Market

      Last Listing Agent Alexander Aquino Douglas Elliman Real Estate

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$940,000
Median Single Family Sale Price
$992,000
Median 2 Bedroom Sale Price
$749,000
Median 1 Bedroom Sale Price
$417,500
Average Price Per Sq Ft
$677
Number of Homes for Sale
2,662
Last 12 months Home Sales
63
Months of Supply
4.40
Median List Price
$998,500
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-4%
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