Southold, NY Homes

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  $1,750,000 Open Sat 11AM - 12:30PM

  • 6 Beds
  • 3 Baths
  • 2,911 Sq Ft

  56861 Private Rd B (Main), Southold, NY 11971

  Dream big, live LARGE! This newly renovated home is ready for it's close-up! The new Chef's Kitchen is designed with easy summer hosting in mind, with new appliances, gorgeous counter-tops and a Hamptons vibe. Large open plan living room with a wood-burning fire-place, and large dining area are ready for your whole tribe! All of the upstairs bedrooms (including the primary suite) have a shared

  

  Regan Battuello

  The Agency Northshore NY

  (934) 200-4963

  56861 Private Rd B (Main), Southold, NY 11971
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  /20

  $8,340 per month

  • 3 Beds
  • 1.5 Baths
  • 1,097 Sq Ft
  • Condo for Rent

  810 Waterview Dr Unit SI ID1261529P, Southold, NY 11971

  The advertised rate of $8,341/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 1, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  810 Waterview Dr Unit SI ID1261529P, Southold, NY 11971
• 

  $475,000 Sold Mar 30, 2026

  4077 Main Bayview Rd, Southold, NY 11971

  • Land
  • 0.92 Acre
  • $516,304 per Acre

  Last Sold Summary

  • 21% Below List Price
  • 143 Days On Market

  Current Estimated Value $1,102,333

  Last Listing Agent Mary Ellen Ellwood Douglas Elliman Real Estate

  4077 Main Bayview Rd, Southold, NY 11971
• 

  Est $1,453,866 Not Listed For Sale

  620 Rogers Rd, Southold, NY 11971

  • 4 Beds
  • 3 Baths
  • Built 1938

  620 Rogers Rd, Southold, NY 11971

  Last Sold Summary

  • 7% Above List Price
  • 34 Days On Market

  Last Sold Price $1,360,000

  Last Listing Agent Eric Elkin Compass Greater NY LLC
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  /41

  $8,200,000

  • 5 Beds
  • 4.5 Baths
  • 4,627 Sq Ft

  1750 Hobart Rd, Southold, NY 11971

  Welcome to a stunning, one-of-a-kind, luxury modern waterfront home in the highly sought-after hamlet of Southold. This custom, newly constructed, residence is perfectly oriented West on Town Creek. Featuring 160’ of waterfront and expansive views of Peconic Bay, it includes a private 6 x 20' dock and an 82’ Trex catwalk. Constructed with every attention to detail, the home includes maximum

  

  Deborah Pirro

  Daniel Gale Sothebys Intl Rlty

  (631) 529-1381

  1750 Hobart Rd, Southold, NY 11971
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  /20

  $12,000 per month

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

  695 Rogers Rd, Southold, NY 11971

  Available for Memorial Day weekend through Mid October. Located in a gorgeous Bay beach private community, just a stone's throw from Southold Bay (3rd house from the Bay). Waterviews from many rooms and the large backyard. Immaculate, light filled, 5 bedroom/2 bath charmer with room for all. Features include walkout deck, a library, sunroom w/gorgeous Bay views, outdoor showerhouse. Super

  Kathleen Travers Douglas Elliman Real Estate

  695 Rogers Rd, Southold, NY 11971
• 

  $2,700,000 Sold Jan 12, 2026

  5805 Main Bayview Rd, Southold, NY 11971

  • 4 Beds
  • 3 Baths
  • 3,253 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $830/SF
  • 65 Days On Market

  Current Estimated Value $2,728,261

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  5805 Main Bayview Rd, Southold, NY 11971
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  Est $1,345,641 Not Listed For Sale

  245 Clearview Ave W, Southold, NY 11971

  • 3 Beds
  • 3 Baths
  • 2,450 Sq Ft
  • Built 2018

  245 Clearview Ave W, Southold, NY 11971

  Last Sold Summary

  • 2% Above List Price
  • $541/SF
  • 9 Days On Market

  Last Sold Price $1,325,000

  Last Listing Agent Mariah Mills Daniel Gale Sotheby's
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  /20

  $989,000

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  2070 Cedar Dr, Southold, NY 11971

  2070 Cedar Drive offers the kind of North Fork lifestyle buyers search for but rarely find — a welcoming home in a peaceful setting. There’s a sandy neighborhood beach right across the street and it’s positioned near other beaches, marinas, and North Fork vineyards. Located in a highly desirable Southold waterfront enclave, the property presents a compelling opportunity for both lifestyle buyers

  

  Dawn Watson

  Serhant East End LLC

  (631) 840-6859

  2070 Cedar Dr, Southold, NY 11971
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  /27

  $17,681 per month

  • 4 Beds
  • 3 Baths
  • 3,196 Sq Ft
  • Condo for Rent

  1345 Long Creek Dr Unit SI ID1512339P, Southold, NY 11971

  The advertised rate of $17,681/month is the lowest available price, based on a 30 day(s) stay with a move-in date of May 20, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  1345 Long Creek Dr Unit SI ID1512339P, Southold, NY 11971
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  $1,150,000 Sold Jan 27, 2026

  2120 Brigantine Dr, Southold, NY 11971

  • 4 Beds
  • 4 Baths
  • 2,000 Sq Ft
  • Built 1972

  Last Sold Summary

  • 8% Below List Price
  • $575/SF
  • 76 Days On Market

  Current Estimated Value $1,208,478

  Last Listing Agent Barbara Poliwoda Douglas Elliman Real Estate

  2120 Brigantine Dr, Southold, NY 11971
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  Est $856,734 Not Listed For Sale

  43475 Route 25, Peconic, NY 11958

  • 4 Beds
  • 1.5 Baths
  • 2,400 Sq Ft
  • Built 1890

  43475 Route 25, Peconic, NY 11958

  Last Sold Summary

  • 25% Above List Price
  • $285/SF
  • 29 Days On Market

  Last Sold Price $685,000

  Last Listing Agent Paul Loeb Douglas Elliman Real Estate
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  /30

  $625,000 Pending

  • 2 Beds
  • 1 Bath
  • 973 Sq Ft

  875 Oak Ave, Southold, NY 11971

  Come home to the quintessential historic (ca. 1938) coastal bungalow in Goose Bay Estates. This cabin meets cottage offers a rare opportunity to own a piece of paradise with peaceful water views and exclusive community beach access just 4 houses down the lane. Enjoy the feel of an upstate cabin with pine paneling and a woodburning stove, while gazing at the serene waters of Goose Creek. Whether

  

  Cheryl Schneider

  The Agency Northshore NY

  (631) 772-0876

  875 Oak Ave, Southold, NY 11971
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  /18

  $25,000 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  2845 Hobart Rd, Southold, NY 11971

  Mint mid-century modern cottage offering 3 bedrooms and 2 baths, ideally located just 100 yards from sandy Founders Landing beach. The interior features clean, modern lines, anchored by a fireplace and expansive picture windows that fill the space with natural light and capture beautiful water views. Outdoors, your backyard with fire pit and outdoor shower creates an ideal setting for summer

  Eric Elkin Compass Greater NY LLC

  2845 Hobart Rd, Southold, NY 11971
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  $2,225,000 Sold Mar 20, 2026

  285 Blue Marlin Dr, Southold, NY 11971

  • 4 Beds
  • 4.5 Baths
  • 2,842 Sq Ft
  • Built 2025

  Last Sold Summary

  • 18% Below List Price
  • $783/SF
  • 248 Days On Market

  Current Estimated Value $2,449,000

  Last Listing Agent Connie Liappas Compass Greater NY LLC

  285 Blue Marlin Dr, Southold, NY 11971
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  Est $3,755,000 Not Listed For Sale

  200 Deer Run, Southold, NY 11971

  • 5 Beds
  • 9 Baths
  • 6,000 Sq Ft
  • Built 2015

  200 Deer Run, Southold, NY 11971

  Last Sold Summary

  • 1% Below List Price
  • $633/SF
  • 88 Days On Market

  Last Sold Price $3,800,000

  Last Listing Agent Carol Szynaka Daniel Gale Sotheby's
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  /41

  $1,399,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,690 Sq Ft

  1025 Long Creek Dr, Southold, NY 11971

  Welcome to your North Fork waterfront oasis in highly desirable Yennecott Park, offering the rare combination of privacy, natural beauty, and effortless access to all. Perfectly positioned along scenic Long Creek with views toward Hashamomuck Preserve, this 4-bedroom waterfront home delivers a relaxed coastal lifestyle. Set on .75 acres with lush mature landscaping and generous water frontage,

  Susan Orioli Engel & Volkers North Fork

  1025 Long Creek Dr, Southold, NY 11971
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  /17

  $6,000 per month

  • 4 Beds
  • 4 Baths
  • 1,800 Sq Ft
  • House for Rent

  215 Leon Rd, Southold, NY 11971

  Enjoy this spacious vacation rental located just a short distance from Southold Town Beach. With room for the whole family, this home features three en-suite bedrooms plus an additional bedroom and full bath. The well-equipped kitchen opens to the dining and living rooms, where a cozy fireplace adds charm and warmth. Sliding glass doors lead to a deck overlooking a large backyard, perfect for

  Jeanmarie Bay William Raveis New York LLC

  215 Leon Rd, Southold, NY 11971
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  $2,400,000 Sold Mar 03, 2026

  1955 Laurel Ave, Southold, NY 11971

  • 3 Beds
  • 3.5 Baths
  • 3,210 Sq Ft
  • Built 2025

  Last Sold Summary

  • $748/SF
  • 104 Days On Market

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  1955 Laurel Ave, Southold, NY 11971
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  Est $1,479,677 Not Listed For Sale

  670 Kenneys Rd, Southold, NY 11971

  • 4 Beds
  • 2.5 Baths
  • 2,417 Sq Ft
  • Built 2025

  670 Kenneys Rd, Southold, NY 11971

  Last Sold Summary

  • 22% Below List Price
  • $786/SF
  • 4 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Robert Merolla Aurora Property Group
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  /25

  $2,799,000

  • 8 Beds
  • 7 Baths
  • 5,600 Sq Ft

  1350 Hortons Ln, Southold, NY 11971

  2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Prime Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional 2-acre vacant lot, tucked away in a serene, secluded setting --- Yet just minutes from downtown, pristine beaches, and world-class vineyards, shopping and dining. Plans are in-place for a "To Be Built"

  Thomas McCarthy Thomas J McCarthy Real Estate

  1350 Hortons Ln, Southold, NY 11971
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  /10

  $4,000 per month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • House for Rent

  8515 Soundview Ave, Southold, NY 11971

  Tucked away on the peaceful edge of freshwater Great Pond in Southold, this delightful 2-bedroom, 1-bath cottage offers the perfect blend of comfort and charm. Enjoy quiet mornings with water views and spend your days kayaking, paddle boarding, or fishing right from your backyard. Barbecue and dine on the spacious deck with a sunset view of the lake. Ideally situated just moments from Kenny's

  Nicole Fitzgerald Signature Premier Properties

  8515 Soundview Ave, Southold, NY 11971
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  $2,075,000 Sold Oct 23, 2025

  20210 Soundview Ave, Southold, NY 11971

  • 4 Beds
  • 5.5 Baths
  • 4,671 Sq Ft
  • Built 1984

  Last Sold Summary

  • 15% Below List Price
  • $444/SF
  • 79 Days On Market

  Current Estimated Value $2,094,229

  Last Listing Agent Marco Maida Compass Greater NY LLC

  20210 Soundview Ave, Southold, NY 11971
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  Not Listed For Sale

  2555 Youngs Ave Unit 5E, Southold, NY 11971

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1985

  2555 Youngs Ave Unit 5E, Southold, NY 11971

  Last Sold Summary

  • $488/SF
  • 35 Days On Market

  Last Sold Price $585,000

  Last Listing Agent Timothy O'Keefe Signature Premier Properties
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  /3

  $1,400,000

  • 4 Beds
  • 3.5 Baths
  • 2,215 Sq Ft

  500 Summer Ln, Southold, NY 11971

  The classic North Fork lifestyle you have been waiting for has finally arrived. Nestled in a quiet Southold neighborhood, 500 Summer Lane offers the rare opportunity to create a retreat just moments from the beaches, vineyards, and beloved local destinations that define the North Fork. Here, tranquility meets convenience—you’re never far from the shoreline or the vibrant heartbeat of the

  Catherine Flood Compass Greater NY LLC

  500 Summer Ln, Southold, NY 11971
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  /28

  $9,500 per month

  • 3 Beds
  • 3 Baths
  • 2,280 Sq Ft
  • House for Rent

  205 Pine Ave, Southold, NY 11971

  A relaxed North Fork summer retreat with a private beaches, a pool for long afternoons, and easy access to vineyards, farmstands, and waterfront dining. Summer on the North Fork begins at 205 Pine Avenue!Located within the coveted Goose Bay Estates private beach community, this beautifully maintained Southold home offers access to two private beaches at the end of the street—perfect for

  Barbara Poliwoda Douglas Elliman Real Estate

  205 Pine Ave, Southold, NY 11971
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  $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 $1,024,124

  Last Listing Agent Donna Fakiris Modern Age Realty Group LLC

  58315 North Rd, Greenport, NY 11944
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  Est $1,052,670 Not Listed For Sale

  1150 Kenneys Rd, Southold, NY 11971

  1150 Kenneys Rd, Southold, NY 11971

  Last Sold Summary

  • 5% Above List Price
  • 59 Days On Market

  Last Sold Price $998,500

  Last Listing Agent Thomas McCarthy Thomas J McCarthy Real Estate
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  /41

  $2,795,000

  • 4 Beds
  • 4.5 Baths
  • 4,327 Sq Ft

  1815 Laurel Ave, Southold, NY 11971

  Welcome to the Laurel Collection by Marrcon. New Luxury Construction located in the heart of the North Fork's Town of Southold. This home is situated on .80 acres & boasts 4,327 SF of living space with 4 bedrooms and 4.5 baths and combines clean lines of modern design with the allure of North Fork chic. This home comes with Authentic Western Red Cedar Shingle siding and a stucco accented stair

  Kristy Naddell Douglas Elliman Real Estate

  1815 Laurel Ave, Southold, NY 11971
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  /8

  $5,000 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  8415 Soundview Ave, Southold, NY 11971

  Step inside this charming 2 bedroom, 1 bath bungalow nestled on the serene shores of Great Pond in Southold. This cozy waterfront retreat offers tranquil water views and is just around the corner from Kenny's Beach and the popular Little Fish restaurant. Enjoy kayaking, paddle boarding, and fishing right from your backyard. Centrally located in the heart of the North Fork, you're perfectly

  Nicole Fitzgerald Signature Premier Properties

  8415 Soundview Ave, Southold, NY 11971
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  $1,247,000 Sold Jul 25, 2025

  1085 Gin Ln, Southold, NY 11971

  • 4 Beds
  • 4 Baths
  • 3,400 Sq Ft
  • Built 1975

  Last Sold Summary

  • 4% Below List Price
  • $367/SF
  • 72 Days On Market

  Current Estimated Value $1,314,170

  Last Listing Agent Nancy Cervelli Daniel Gale Sothebys Intl Rlty

  1085 Gin Ln, Southold, NY 11971
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  Not Listed For Sale

  200 Crittenden Ln, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1964

  200 Crittenden Ln, Southold, NY 11971

  Last Sold Summary

  • $594/SF
  • 10 Days On Market

  Last Sold Price $926,000

  Last Listing Agent Katie DiGregorio Corcoran
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  /20

  $1,949,000

  • 4 Beds
  • 3.5 Baths
  • 3,245 Sq Ft

  265 Arshamomaque Ave, Southold, NY 11971

  This beautiful Newly Constructed Modern Craftsman/Cottage style home, tucked away down a private lane, boasting 3245 sq' interior living space, black onyx saltwater pool and serene wooded property while providing access to two exclusive bayside access areas located in desirable Beixedon Estates. This beautiful newly constructed home is ideally situated between quaint Southold Town and the vibrant

  Cathleen Dolson Corcoran

  265 Arshamomaque Ave, Southold, NY 11971
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  /41

  $8,000 per month

  • 6 Beds
  • 3.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  100 W Shore Dr, Southold, NY 11971

  Set in the highly sought-after Reydon Shores community, 100 W Shore Dr, Southold is a rare dog-friendly North Fork waterfront seasonal rental with your own private, sandy beach and sweeping bay views to Shelter Island. This renovated classic offers three levels of living with a great room and sunroom, 6 bedrooms, 3.5 baths, two wood-burning fireplaces, and a huge Trex deck built for sunset

  Basil Boziotis Compass Greater NY LLC

  100 W Shore Dr, Southold, NY 11971
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  $791,000 Sold Dec 02, 2025

  155 Shepard Dr, Southold, NY 11971

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1988

  Last Sold Summary

  • 21% Below List Price
  • $494/SF
  • 217 Days On Market

  Current Estimated Value $816,190

  Last Listing Agent Isaac Israel Richmond Realty Corp

  155 Shepard Dr, Southold, NY 11971
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  Est $1,883,539 Not Listed For Sale

  650 Old Harbor Rd, Southold, NY 11971

  • 2 Beds
  • 3 Baths
  • 2,025 Sq Ft
  • Built 1971

  650 Old Harbor Rd, Southold, NY 11971

  Last Sold Summary

  • 3% Below List Price
  • $958/SF
  • 27 Days On Market

  Last Sold Price $1,940,000

  Last Listing Agent Bridget Elkin Compass Greater NY LLC
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  /15

  $1,499,000

  • 3 Beds
  • 4 Baths
  • 2,900 Sq Ft

  535 Bay Home Rd, Southold, NY 11971

  .

  Kim Pirreca BERKSHIRE HATHAWAY

  535 Bay Home Rd, Southold, NY 11971
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  /32

  $44,000 per month

  • 4 Beds
  • 4.5 Baths
  • 2,500 Sq Ft
  • House for Rent

  70 Arshamomaque Ave, Southold, NY 11971

  Southold, North Fork AUGUST 1-14, 2026 Rental: Heaven Off Main. Chic new retreat with ultra vacation vibe. 4 en suite bedrooms, each with a different theme and a full bath, complement the 'public' rooms designed for entertaining. Home opens up to poolside terrace and gorgeous sun! Located in the private bayfront beach community of Beixedon. Book your stay today. Pets on an individual basis.

  Nicholas Planamento William Raveis New York LLC

  70 Arshamomaque Ave, Southold, NY 11971
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  $1,307,000 Sold Nov 14, 2025

  3520 Old Rd N, Southold, NY 11971

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • Built 1989

  Last Sold Summary

  • 98,990% Above List Price
  • $436/SF
  • 16 Days On Market

  Current Estimated Value $1,299,591

  Last Listing Agent Roseann Prussen Signature Premier Properties

  3520 Old Rd N, Southold, NY 11971
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  Est $1,522,164 Not Listed For Sale

  500 Arshamomaque Ave, Southold, NY 11971

  • 4 Beds
  • 5 Baths
  • 2,334 Sq Ft
  • Built 2024

  500 Arshamomaque Ave, Southold, NY 11971

  Last Sold Summary

  • 3% Below List Price
  • $674/SF
  • 50 Days On Market

  Last Sold Price $1,573,500

  Last Listing Agent Lisa Davey LI Probate Realty Inc

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