Vineyard Haven, MA Homes

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  /15

  $1,050,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,547 Sq Ft

  78 Forest Ave, Oak Bluffs, MA 02557

  This beautifully updated four-bedroom, two-bath home combines thoughtful design with quality craftsmanship. The open floor plan features reclaimed wood floors and custom built-in cabinetry. The stunning kitchen with handcrafted cabinets and stainless steel appliances features slate flooring from Vermont and PaperStone® countertops. Every detail was intentionally chosen, as the owners lovingly

  Jennifer O'hanlon Compass LLC

  78 Forest Ave, Oak Bluffs, MA 02557
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  /2

  $1,000,000 Sold Dec 30, 2025

  22 Wing Rd, Oak Bluffs, MA 02557

  • 3 Beds
  • 1.5 Baths
  • 1,136 Sq Ft
  • Built 1900

  Last Sold Summary

  • $880/SF
  • 0 Days On Market

  Current Estimated Value $1,010,764

  Last Listing Agent LINK Email Cache LINK

  22 Wing Rd, Oak Bluffs, MA 02557
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  /10

  Not Listed For Sale

  0 Shawanue Ave Unit 42704, Oak Bluffs, MA 02557

  0 Shawanue Ave Unit 42704, Oak Bluffs, MA 02557

  Last Sold Summary

  • 70 Days On Market

  • Last Sold Price $550,000
  • Feb 28, 2025

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's
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  /10

  $1,425,000

  • Land
  • 3.01 Acres
  • $473,422 per Acre

  38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568

  The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's easy to understand why this property is so special. There's a generous designated building envelope of

  Elissa Lash Tea Lane Associates

  38 Fire Tower Rd Unit 40.2, West Tisbury, MA 02568
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  /16

  $1,135,000 Sold Oct 31, 2025

  30 Teaberry Ln, Edgartown, MA 02539

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2002

  Last Sold Summary

  • $844/SF
  • 10 Days On Market

  Current Estimated Value $1,121,172

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty

  30 Teaberry Ln, Edgartown, MA 02539
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  /14

  Not Listed For Sale

  3 Hope's Way, Oak Bluffs, MA 02568

  • 2 Beds
  • 2.5 Baths
  • Built 2023

  3 Hope's Way, Oak Bluffs, MA 02568

  Last Sold Summary

  • $289/SF
  • 0 Days On Market

  • Last Sold Price $695,000
  • Sep 05, 2023

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc
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  /13

  $1,645,000

  • Land
  • 3.32 Acres
  • $495,482 per Acre

  26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575

  Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides - a setting unlike

  Dawn Bellante-Holand Sandpiper Realty

  26 Flint Hill Rd Unit 3B, West Tisbury, MA 02575
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  /9

  $1,500,000 Sold Mar 03, 2026

  515 Edgartown Rd, Vineyard Haven, MA 02568

  • 6 Beds
  • 3 Baths
  • 5,418 Sq Ft
  • Built 1997

  Last Sold Summary

  • $277/SF
  • 0 Days On Market

  Current Estimated Value $1,899,257

  Last Listing Agent LINK Email Cache LINK

  515 Edgartown Rd, Vineyard Haven, MA 02568
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  /5

  Not Listed For Sale

  9 Crowell Ln, Tisbury, MA 02568

  9 Crowell Ln, Tisbury, MA 02568

  Last Sold Summary

  • 220 Days On Market

  • Last Sold Price $675,000
  • Apr 18, 2024

  Last Listing Agent Julianna Flanders Flanders Real Estate
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  /18

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  10 Winthrop Ave, Oak Bluffs, MA 02557

  Oak Bluffs- Fully renovated and just completed, this three-bedroom, two-bath home is ready for immediate occupancy! Ideally located just moments from downtown Oak Bluffs and the vibrant harborfront, you’ll enjoy easy access to shops, dining, beaches, and ferry connections. Featuring modern updates throughout, this home offers the perfect blend of comfort and convenience.

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  10 Winthrop Ave, Oak Bluffs, MA 02557
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  /55

  $1,100,000 Sold Oct 31, 2025

  145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1999

  Last Sold Summary

  • 19% Below List Price
  • $579/SF
  • 91 Days On Market

  Current Estimated Value $1,137,628

  Last Listing Agent Emily Flake Viewpoints

  145 Sandpiper Ln Unit 10, Vineyard Haven, MA 02568
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  /25

  Not Listed For Sale

  40 Hidden Cove Rd Unit 15, Oak Bluffs, MA 02557

  • 3 Beds
  • 2.5 Baths
  • 1,898 Sq Ft
  • Built 1983

  40 Hidden Cove Rd Unit 15, Oak Bluffs, MA 02557

  Last Sold Summary

  • $483/SF
  • 140 Days On Market

  • Last Sold Price $917,500
  • Mar 10, 2025

  Last Listing Agent Stephanie Roache Donnelly + Co
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  /36

  $1,275,000 Open Sat 11:30AM - 12:30PM

  • 3 Beds
  • 1 Bath
  • 1,033 Sq Ft

  9 Brunswick Ave, Oak Bluffs, MA 02557

  PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully & extensively UPDATED INSIDE AND OUT. Enjoy peace of mind w/ NEW septic system, siding, windows, water line from the street, & upgraded electrical & plumbing. Interior boasts new flooring, insulation, fresh paint, a stylishly

  Alice Pierce Coldwell Banker Realty - Hingham

  9 Brunswick Ave, Oak Bluffs, MA 02557
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  /25

  $3,925,000 Sold Sep 24, 2025

  966 Main St, Vineyard Haven, MA 02568

  • 8 Beds
  • 4.5 Baths
  • 3,954 Sq Ft
  • Built 1730

  Last Sold Summary

  • 7% Below List Price
  • $993/SF
  • 4 Days On Market

  Current Estimated Value $4,637,165

  Last Listing Agent Grant Rudolph Viewpoints

  966 Main St, Vineyard Haven, MA 02568
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  /11

  Est $976,697 Not Listed For Sale

  7 Richmond Ave, Oak Bluffs, MA 02568

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1970

  7 Richmond Ave, Oak Bluffs, MA 02568

  Last Sold Summary

  • 22% Above List Price
  • $714/SF
  • 25 Days On Market

  • Last Sold Price $800,000
  • Jun 20, 2023

  Last Listing Agent Richard Coutinho Wiggy's Pond Real Estate
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  /29

  $6,795,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,589 Sq Ft

  57 Hines Point Rd, Vineyard Haven, MA 02568

  Lily Hill - a rare Hines Point offering that includes a waterfront home with exquisite views, a deep water mooring and dock, and 130 feet of private fine-sand beach. Poised on a knoll on the western shore of the Lagoon, Lily Hill evokes a more peaceful time with sweeping views of the sky and water. Enjoy a swim at your private beach morning, noon or night. Watch the play of light across the water

  Elissa Lash Tea Lane Associates

  57 Hines Point Rd, Vineyard Haven, MA 02568
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  /37

  $2,100,000 Sold Nov 07, 2025

  22 Greenleaf Ave, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $1,306/SF
  • 201 Days On Market

  Current Estimated Value $2,063,068

  Last Listing Agent Jennifer O'hanlon Compass

  22 Greenleaf Ave, Oak Bluffs, MA 02557
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  /16

  Not Listed For Sale

  19 2nd Ave, Oak Bluffs, MA 02557

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft
  • Built 1988

  19 2nd Ave, Oak Bluffs, MA 02557

  Last Sold Summary

  • $1,165/SF
  • 7 Days On Market

  • Last Sold Price $820,000
  • Sep 19, 2024

  Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard
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  /36

  $4,695,000

  • 7 Beds
  • 4.5 Baths
  • 5,320 Sq Ft

  8 Fresh Pond Rd, Oak Bluffs, MA 02557

  The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an

  Jarrett Hurwitz Keller Williams Realty

  8 Fresh Pond Rd, Oak Bluffs, MA 02557
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  /25

  $1,000,000 Sold Mar 31, 2026

  113 Leonard Cir, Vineyard Haven, MA 02568

  • 4 Beds
  • 2 Baths
  • 1,306 Sq Ft
  • Built 1997

  Last Sold Summary

  • 26% Below List Price
  • $766/SF
  • 244 Days On Market

  Current Estimated Value $1,110,102

  Last Listing Agent Karen Overtoom Karen M. Overtoom R.E.

  113 Leonard Cir, Vineyard Haven, MA 02568
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  /55

  Not Listed For Sale

  28 & 18 Hillbrook Ln, West Tisbury, MA 02575

  • 11 Beds
  • 9.5 Baths
  • 4,985 Sq Ft
  • Built 1975

  28 & 18 Hillbrook Ln, West Tisbury, MA 02575

  Last Sold Summary

  • $1,384/SF
  • 9 Days On Market

  • Last Sold Price $6,900,000
  • May 09, 2023

  Last Listing Agent Candy DaRosa Feiner Real Estate
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  /15

  $950,000

  • 2 Beds
  • 1 Bath
  • 1,074 Sq Ft

  22 Firehouse Ln, Oak Bluffs, MA 02557

  Tucked away on a quiet side street just 0.7 miles from Circuit Avenue, this charming Oak Bluffs cottage offers the rare combination of privacy and proximity to town. The original two-bedroom, one-bath home was thoughtfully expanded to include a bright great room that opens directly to a large fenced yard — ideal for outdoor dining, pets, or simply enjoying Vineyard summers. The property is

  Jennifer O'hanlon Compass LLC

  22 Firehouse Ln, Oak Bluffs, MA 02557
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  /7

  $835,000 Sold Feb 06, 2026

  136 W Spring St, Vineyard Haven, MA 02568

  • 1 Bed
  • 1 Bath
  • 534 Sq Ft
  • Built 2017

  Last Sold Summary

  • 12% Below List Price
  • $1,564/SF
  • 130 Days On Market

  Current Estimated Value $1,371,489

  Last Listing Agent David Dickinson Compass

  136 W Spring St, Vineyard Haven, MA 02568
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  /6

  Not Listed For Sale

  5 Tori Ln, Oak Bluffs, MA 02568

  5 Tori Ln, Oak Bluffs, MA 02568

  Last Sold Summary

  • 20 Days On Market

  • Last Sold Price $580,000
  • Sep 29, 2023

  Last Listing Agent Jim Feiner Feiner Real Estate
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  /41

  $3,499,000 Pending

  • 5 Beds
  • 6 Baths
  • 3,800 Sq Ft

  35 Mount Aldworth Rd, Vineyard Haven, MA 02568

  Welcome to a stunning new construction-in-progress home that blends modern coastal living with the island charm. Set on an elevated site with distant water views, this thoughtfully designed living space, plus an additional 900 square foot basement with both finished and unfinished areas—perfect for a media room, gym, office or storage.Outside, enjoy your own private retreat creating the ideal

  Jennifer DaSilva Compass | Point B

  35 Mount Aldworth Rd, Vineyard Haven, MA 02568
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  /2

  $1,100,000 Sold Dec 29, 2025

  200 Edgartown Vineyard Haven Rd Unit 1, Oak Bluffs, MA 02539

  • Land
  • 1.37 Acres
  • $802,920 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent LINK Email Cache LINK

  200 Edgartown Vineyard Haven Rd Unit 1, Oak Bluffs, MA 02539
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  /6

  Not Listed For Sale

  00 Crowell Lane - Lot 3 4, Vineyard Haven, MA 02568

  00 Crowell Lane - Lot 3 4, Vineyard Haven, MA 02568

  Last Sold Summary

  • 287 Days On Market

  • Last Sold Price $700,000
  • Apr 30, 2024

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's
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  /37

  $1,195,000

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  4 Rock Pond Rd, Vineyard Haven, MA 02568

  4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and sunlight

  Kerry Quinlan-Potter Breakwater MV

  4 Rock Pond Rd, Vineyard Haven, MA 02568
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  /24

  $1,875,000 Sold Dec 08, 2025

  14 Rebekahs Way, Vineyard Haven, MA 02568

  • 5 Beds
  • 3 Baths
  • 1,916 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Below List Price
  • $979/SF
  • 22 Days On Market

  Current Estimated Value $1,829,881

  Last Listing Agent Sheila Morse Island Real Estate

  14 Rebekahs Way, Vineyard Haven, MA 02568
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  Not Listed For Sale

  40 Hidden Cove Rd Unit 7, Oak Bluffs, MA 02557

  • 3 Beds
  • 3.5 Baths
  • 2,754 Sq Ft
  • Built 1983

  40 Hidden Cove Rd Unit 7, Oak Bluffs, MA 02557

  Last Sold Summary

  • $507/SF
  • 0 Days On Market

  • Last Sold Price $1,395,000
  • Sep 19, 2023

  Last Listing Agent Dawn Bellante-Holand Sandpiper Realty
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  /19

  $2,950,000

  • 3 Beds
  • 3 Baths
  • 3,506 Sq Ft

  24 Cournoyer Rd, Vineyard Haven, MA 02568

  This mixed use building is zoned for residential and commercial use. It is extremely well built with an emphasis on non-toxic materials throughout. High ceilings on all three levels. There are radiant floors mixed with forced hot air/AC. The building offers a variety of uses for a new owner. The existing spaces are very versatile and would be ideal for any service oriented business given the

  Jill Napior Tea Lane Associates

  24 Cournoyer Rd, Vineyard Haven, MA 02568
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  /28

  $1,270,000 Sold May 23, 2025

  60 Prospect Ave, Oak Bluffs, MA 02557

  • 3 Beds
  • 2 Baths
  • 2,192 Sq Ft
  • Built 1940

  Last Sold Summary

  • 6% Below List Price
  • $579/SF
  • 57 Days On Market

  Current Estimated Value $1,257,037

  Last Listing Agent Marilyn Moses Ocean Park Realty Inc

  60 Prospect Ave, Oak Bluffs, MA 02557
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  Not Listed For Sale

  609 State Rd, West Tisbury, MA 02575

  609 State Rd, West Tisbury, MA 02575

  Last Sold Summary

  • 423 Days On Market

  • Last Sold Price $550,000
  • Aug 30, 2024

  Last Listing Agent Candy DaRosa Feiner Real Estate
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  /37

  $2,495,000

  • 6 Beds
  • 2.5 Baths
  • 2,577 Sq Ft

  16 Atlantic Ave, Oak Bluffs, MA 02557

  Oak Bluffs | East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The stately five-bedroom main residence is rich in character and nostalgic charm, thoughtfully updated to enhance comfort for year-round living. Tucked privately at the rear of the

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  16 Atlantic Ave, Oak Bluffs, MA 02557
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  /45

  $1,225,000 Sold May 19, 2025

  51 Head of the Pond Rd, Vineyard Haven, MA 02568

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft
  • Built 1986

  Last Sold Summary

  • 23% Below List Price
  • $710/SF
  • 338 Days On Market

  Current Estimated Value $1,299,790

  Last Listing Agent Bruce Stuart Bruce Stuart and Associates

  51 Head of the Pond Rd, Vineyard Haven, MA 02568
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  /19

  Not Listed For Sale

  37 Circuit Ave Unit 2, Oak Bluffs, MA 02557

  • 2 Beds
  • 1 Bath
  • 797 Sq Ft
  • Built 1900

  37 Circuit Ave Unit 2, Oak Bluffs, MA 02557

  Last Sold Summary

  • $1,099/SF
  • 7 Days On Market

  • Last Sold Price $876,000
  • Aug 06, 2024

  Last Listing Agent Carol McManus C McManus Realty Group
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  /18

  $799,000 Open Sat 11:30AM - 12:30PM

  • 2 Beds
  • 1 Bath
  • 623 Sq Ft

  1 Pease Ave, Oak Bluffs, MA 02557

  Tucked away on a quiet no-thru street near the Tabernacle and Trinity Park, this meticulously maintained year-round Martha’s Vineyard Camp Meeting Association cottage blends charm and convenience. Thoughtful 2023 updates—including a new kitchen with stainless steel appliances, refreshed bathroom, upgraded insulation and electrical, three mini-splits, onsite laundry, spiral staircase, and new

  Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

  1 Pease Ave, Oak Bluffs, MA 02557
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  /47

  $1,250,000 Sold Sep 25, 2025

  58 Weaver Ct, Vineyard Haven, MA 02568

  • 4 Beds
  • 3 Baths
  • 2,210 Sq Ft
  • Built 1969

  Last Sold Summary

  • 22% Below List Price
  • $566/SF
  • 230 Days On Market

  Current Estimated Value $1,394,539

  Last Listing Agent Skip Dostal Martha's Vineyard R.E.

  58 Weaver Ct, Vineyard Haven, MA 02568
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  Not Listed For Sale

  5 & 7 Lyme St, Oak Bluffs, MA 02557

  • 5 Beds
  • 3 Baths
  • 1,999 Sq Ft
  • Built 1960

  5 & 7 Lyme St, Oak Bluffs, MA 02557

  Last Sold Summary

  • $650/SF
  • 26 Days On Market

  • Last Sold Price $1,300,000
  • Oct 18, 2024

  Last Listing Agent Rene Ben David Ocean Park Realty Inc
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  /31

  $1,488,000

  • 5 Beds
  • 4 Baths
  • 2,884 Sq Ft

  39 Ferro Way, Vineyard Haven, MA 02568

  Tucked away on a quiet cul-de-sac, this beautifully maintained single-family home offers the perfect blend of privacy and convenience. Built in 2020, the property features 5 spacious bedrooms and 4 full bathrooms across 2,884 square feet of thoughtfully designed living space.Set on a generous 15,593 sq ft lot, the home provides ample outdoor space with exciting potential for a guest house,

  Emily Flake Viewpoints

  39 Ferro Way, Vineyard Haven, MA 02568

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