9,682

Chatham, MA Homes

Section Image
    • 98 Attucks Trail, Chatham, MA 02633
      98 Attucks Trail, Chatham, MA 02633
      98 Attucks Trail, Chatham, MA 02633
      /40

      Est $3,809,314 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,915 Sq Ft

      98 Attucks Trail, Chatham, MA 02633

      98 Attucks Trail, Chatham, MA 02633
  • 85 Cedar St, Chatham, MA 02633
    85 Cedar St, Chatham, MA 02633
    85 Cedar St, Chatham, MA 02633
    /90

    $4,975,000

    • 5 Beds
    • 3.5 Baths
    • 3,080 Sq Ft

    85 Cedar St, Chatham, MA 02633

    ** Pinkwink, Circa 1850** - A beautifully updated antique in Chatham on 1.48 acres. Five bedrooms--four in the main house, one in the two-room guest suite above the detached two-car garage with private deck and screened in porch below. The main house features a large sunlit chef's kitchen with cathedral ceiling and top-tier appliances, wood floors, spacious dining room with fireplace, living room

    Tim Bailey John C Ricotta & Assoc.

    85 Cedar St, Chatham, MA 02633
  • 595 Main St Unit 37, Chatham, MA 02633
    595 Main St Unit 37, Chatham, MA 02633
    595 Main St Unit 37, Chatham, MA 02633
    /38

    $2,000,000 Sold Sep 16, 2025

    595 Main St Unit 37, Chatham, MA 02633

    • 3 Beds
    • 3 Baths
    • 2,148 Sq Ft
    • Built 1999

    Last Sold Summary

    • 9% Below List Price
    • $931/SF
    • 18 Days On Market

    Current Estimated Value $2,053,909

    Last Listing Agent Sandra Tanco Kinlin Grover Compass

    595 Main St Unit 37, Chatham, MA 02633
    • 513 Stage Harbor Rd, Chatham, MA 02633
      513 Stage Harbor Rd, Chatham, MA 02633
      513 Stage Harbor Rd, Chatham, MA 02633
      /69

      Not Listed For Sale

      • 6 Beds
      • 7 Baths
      • 5,619 Sq Ft

      513 Stage Harbor Rd, Chatham, MA 02633

      513 Stage Harbor Rd, Chatham, MA 02633
  • 231 Crowell Rd, Chatham, MA 2633
    231 Crowell Rd, Chatham, MA 2633
    231 Crowell Rd, Chatham, MA 2633
    /27

    $1,650,000

    • 1 Bath
    • 2,586 Sq Ft

    231 Crowell Rd, Chatham, MA 2633

    Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport . One bay has a gas heater and the second floor is ready to

    Judith Smith John C Ricotta & Assoc.

    231 Crowell Rd, Chatham, MA 2633
  • 427 Main St, Chatham, MA 2633
    427 Main St, Chatham, MA 2633
    427 Main St, Chatham, MA 2633
    /32

    $399,000 Sold Feb 28, 2025

    427 Main St, Chatham, MA 2633

    • 1 Bed
    • 1 Bath
    • 444 Sq Ft
    • Built 1846

    Last Sold Summary

    • $899/SF
    • 11 Days On Market

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    427 Main St, Chatham, MA 2633
    • 137 Strong Island Rd, Chatham, MA 02633
      137 Strong Island Rd, Chatham, MA 02633
      137 Strong Island Rd, Chatham, MA 02633
      /38

      Est $3,554,271 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 4,199 Sq Ft

      137 Strong Island Rd, Chatham, MA 02633

      137 Strong Island Rd, Chatham, MA 02633
  • 144 Barn Hill Rd, Chatham, MA 02633
    144 Barn Hill Rd, Chatham, MA 02633
    144 Barn Hill Rd, Chatham, MA 02633
    /24

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft

    144 Barn Hill Rd, Chatham, MA 02633

    Ideally situated in the sought-after Hardings Beach area, this home offers views of Sulphur Springs and an unbeatable location within walking distance to the beach along a sidewalk. Nestled off of the road, it is just minutes from local family friendly favorites like Mac's Seafood, Liberty Bakery, Pate's, Dogfish Taco, and Hey Joe Jam. Thoughtfully upgraded over the years, the home features new

    Chris Rhinesmith Compass Massachusetts, LLC

    144 Barn Hill Rd, Chatham, MA 02633
  • 912 Main St Unit 310, Chatham, MA 02633
    912 Main St Unit 310, Chatham, MA 02633
    912 Main St Unit 310, Chatham, MA 02633
    /7

    $410,000 Sold Dec 31, 2024

    912 Main St Unit 310, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,177 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $348/SF
    • 19 Days On Market

    Current Estimated Value $418,500

    Last Listing Agent Tom McGreevy Peterson Realty Inc.

    912 Main St Unit 310, Chatham, MA 02633
    • 146 Strong Island Rd, Chatham, MA 02633
      146 Strong Island Rd, Chatham, MA 02633
      146 Strong Island Rd, Chatham, MA 02633
      /84

      Est $4,860,997 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 4,142 Sq Ft

      146 Strong Island Rd, Chatham, MA 02633

      146 Strong Island Rd, Chatham, MA 02633
  • 41 Woodland Rd, South Chatham, MA 02659
    41 Woodland Rd, South Chatham, MA 02659
    41 Woodland Rd, South Chatham, MA 02659
    /22

    $795,000 Pre-Foreclosure

    • 3 Beds
    • 2 Baths
    • 1,662 Sq Ft

    41 Woodland Rd, South Chatham, MA 02659

    Opportunity Knocks! Diamond in the rough awaits builders/ investors for this vintage 1960 3 BED/2BA Colonial, 1st time ever on the market. Home has good bones with hardwood floors in bedrooms, living and dining....but best of all the fabulous location is just 3/10 of a mile to either Forest Beach Rd or Pleasant St. beaches! Town Tennis courts nearby, dining in So. Chatham or head into Chatham or

    Phyllis Power Compass

    41 Woodland Rd, South Chatham, MA 02659
  • 114 Bucks Creek Rd, Chatham, MA 02633
    114 Bucks Creek Rd, Chatham, MA 02633
    114 Bucks Creek Rd, Chatham, MA 02633
    /46

    $1,385,000 Sold Dec 16, 2025

    114 Bucks Creek Rd, Chatham, MA 02633

    • 4 Beds
    • 3 Baths
    • 2,289 Sq Ft
    • Built 1965

    Last Sold Summary

    • 21% Below List Price
    • $605/SF
    • 84 Days On Market

    Last Listing Agent Adeline Harrington Berkshire Hathaway HomeServices Robert Paul Properties

    114 Bucks Creek Rd, Chatham, MA 02633
    • 192 Eastward Rd, Chatham, MA 02633
      192 Eastward Rd, Chatham, MA 02633
      192 Eastward Rd, Chatham, MA 02633
      /25

      Est $4,011,802 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,514 Sq Ft

      192 Eastward Rd, Chatham, MA 02633

      192 Eastward Rd, Chatham, MA 02633
  • 49 Duck Marsh Ln, Chatham, MA 02633
    49 Duck Marsh Ln, Chatham, MA 02633
    49 Duck Marsh Ln, Chatham, MA 02633
    /36

    $849,000

    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    49 Duck Marsh Ln, Chatham, MA 02633

    Located in Chatham's Countryside neighborhood, this three-bedroom, two-bath cape-style ranch gets plenty of natural light and features a primary suite with a private bath and good closet space. Two additional bedrooms can be used for family, guests, or a home office. The living room has a brick fireplace. A one-car garage and large unfinished basement sits below the home, and the property sits on

    Tim Bailey John C Ricotta & Assoc.

    49 Duck Marsh Ln, Chatham, MA 02633
  • 0 Woodland Way, Chatham, MA 02650
    0 Woodland Way, Chatham, MA 02650
    /2

    $1,000,000 Sold Sep 29, 2025

    0 Woodland Way, Chatham, MA 02650

    • Land
    • 0.49 Acre
    • $2,040,816 per Acre

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Kimberly Howard Christie's International Real Estate Atlantic Brokerage

    0 Woodland Way, Chatham, MA 02650
    • 30 Pine Ln, North Chatham, MA 02650
      30 Pine Ln, North Chatham, MA 02650
      30 Pine Ln, North Chatham, MA 02650
      /43

      Est $2,540,101 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,406 Sq Ft

      30 Pine Ln, North Chatham, MA 02650

      30 Pine Ln, North Chatham, MA 02650
  • 15 Sylvan Way, South Chatham, MA 02659
    15 Sylvan Way, South Chatham, MA 02659
    15 Sylvan Way, South Chatham, MA 02659
    /36

    $899,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,760 Sq Ft

    15 Sylvan Way, South Chatham, MA 02659

    Coastal charm meets timeless elegance at 15 Sylvan Way, tucked on a private lane near beaches, the rail trail, and local dining. This beautifully maintained Colonial is filled with an abundance of natural light from full-length Andersen windows. The open layout features a welcoming living/dining area and a stunning kitchen with high-end appliances, and adjoining mudroom with full bath. Upstairs,

    Jack Bohman Gibson Sotheby's International Realty

    15 Sylvan Way, South Chatham, MA 02659
  • 306 Old Queen Anne Rd, Chatham, MA 02633
    306 Old Queen Anne Rd, Chatham, MA 02633
    306 Old Queen Anne Rd, Chatham, MA 02633
    /41

    $898,000 Sold Oct 30, 2025

    306 Old Queen Anne Rd, Chatham, MA 02633

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $535/SF
    • 14 Days On Market

    Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

    306 Old Queen Anne Rd, Chatham, MA 02633
    • 74 Frost Fish Rd, North Chatham, MA 02650
      74 Frost Fish Rd, North Chatham, MA 02650
      74 Frost Fish Rd, North Chatham, MA 02650
      /47

      Est $2,751,503 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,996 Sq Ft

      74 Frost Fish Rd, North Chatham, MA 02650

      74 Frost Fish Rd, North Chatham, MA 02650
  • 72 Forest Beach Rd, Chatham, MA 02659
    72 Forest Beach Rd, Chatham, MA 02659
    72 Forest Beach Rd, Chatham, MA 02659
    /32

    $1,499,000

    • 6 Beds
    • 5 Baths
    • 2,401 Sq Ft

    72 Forest Beach Rd, Chatham, MA 02659

    South of 28! Renovated Beach Compound with 5 Income-Producing Suites. Just 4/10 of a mile from Nantucket Sound, this iconic South Chatham property blends classic Cape style with modern luxury. Formerly the historic Forest Beach Motel, now meticulously restored and transformed into a stylish coastal compound. Property is offered fully furnished and move-in ready. This unique 6-bedroom, 5-bath

    Michael Magner Berkshire Hathaway HomeServices Robert Paul Properties

    72 Forest Beach Rd, Chatham, MA 02659
  • 912 Main St Unit 207, Chatham, MA 02633
    912 Main St Unit 207, Chatham, MA 02633
    912 Main St Unit 207, Chatham, MA 02633
    /22

    $415,000 Sold Feb 11, 2025

    912 Main St Unit 207, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $384/SF
    • 71 Days On Market

    Current Estimated Value $430,177

    Last Listing Agent Dawn Marie Boynton Berkshire Hathaway HomeServices Robert Paul Properties

    912 Main St Unit 207, Chatham, MA 02633
    • 409 Orleans Rd Unit A, North Chatham, MA 02650
      409 Orleans Rd Unit A, North Chatham, MA 02650
      409 Orleans Rd Unit A, North Chatham, MA 02650
      /25

      Est $507,172 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,038 Sq Ft

      409 Orleans Rd Unit A, North Chatham, MA 02650

      409 Orleans Rd Unit A, North Chatham, MA 02650
  • 86 Champlain Rd, Chatham, MA 02633
    86 Champlain Rd, Chatham, MA 02633
    86 Champlain Rd, Chatham, MA 02633
    /49

    $2,950,000

    • 3 Beds
    • 4.5 Baths
    • 4,361 Sq Ft

    86 Champlain Rd, Chatham, MA 02633

    Hidden gem on Chatham's historic Loop with views of Stage Harbor, the Stage Harbor Lighthouse and Nantucket Sound. Savor the warm summer breezes from this 3 BR, 4.5 Bath, 4,361 sf home with a private deeded footpath to the sandy shores of Stage Harbor. Thoughtfully designed to capture harbor and wetland views, the house features vaulted ceilings, an abundance of windows, hardwood floors and an

    Jack Bohman Gibson Sotheby's International Realty

    86 Champlain Rd, Chatham, MA 02633
  • 17 Menekish Ln, Chatham, MA 02633
    17 Menekish Ln, Chatham, MA 02633
    17 Menekish Ln, Chatham, MA 02633
    /43

    $1,400,000 Sold Feb 20, 2025

    17 Menekish Ln, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 2,124 Sq Ft
    • Built 1984

    Last Sold Summary

    • 22% Below List Price
    • $659/SF
    • 136 Days On Market

    Current Estimated Value $1,486,893

    Last Listing Agent Daren Marvin Sotheby's International Realty

    17 Menekish Ln, Chatham, MA 02633
    • 407 Orleans Rd Unit B, North Chatham, MA 02650
      407 Orleans Rd Unit B, North Chatham, MA 02650
      407 Orleans Rd Unit B, North Chatham, MA 02650
      /18

      Est $514,805 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,013 Sq Ft

      407 Orleans Rd Unit B, North Chatham, MA 02650

      407 Orleans Rd Unit B, North Chatham, MA 02650
  • 238 Cranberry Ln, Chatham, MA 02633
    238 Cranberry Ln, Chatham, MA 02633
    238 Cranberry Ln, Chatham, MA 02633
    /36

    $7,200,000

    • 5 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    238 Cranberry Ln, Chatham, MA 02633

    This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and

    John Burke William Raveis Real Estate & Home Services

    238 Cranberry Ln, Chatham, MA 02633
  • 20 Judys Ln, Chatham, MA 02633
    20 Judys Ln, Chatham, MA 02633
    20 Judys Ln, Chatham, MA 02633
    /35

    $1,095,000 Sold Jul 18, 2025

    20 Judys Ln, Chatham, MA 02633

    • 3 Beds
    • 1.5 Baths
    • 1,064 Sq Ft
    • Built 1960

    Last Sold Summary

    • $1,029/SF
    • 12 Days On Market

    Last Listing Agent Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    20 Judys Ln, Chatham, MA 02633
    • 108 Misty Meadow Ln Unit B, North Chatham, MA 02650
      108 Misty Meadow Ln Unit B, North Chatham, MA 02650
      108 Misty Meadow Ln Unit B, North Chatham, MA 02650
      /27

      Est $671,270 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,551 Sq Ft

      108 Misty Meadow Ln Unit B, North Chatham, MA 02650

      108 Misty Meadow Ln Unit B, North Chatham, MA 02650
  • 27 Fairview Dr, South Chatham, MA 02659
    27 Fairview Dr, South Chatham, MA 02659
    27 Fairview Dr, South Chatham, MA 02659
    /36

    $1,275,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,296 Sq Ft

    27 Fairview Dr, South Chatham, MA 02659

    Tucked in a quiet enclave south of Rt. 28, this inviting South Chatham home blends coastal charm with modern comfort. The open floorplan welcomes you with a fireplaced living room and gleaming hardwood floors that flow seamlessly throughout. The updated kitchen features a center island perfect for casual meals and entertaining, while the spacious, light-filled sunroom offers a serene retreat

    Kathy Doyle Gibson Sotheby's International Realty

    27 Fairview Dr, South Chatham, MA 02659
  • 409 Orleans Rd Unit B, North Chatham, MA 02650
    409 Orleans Rd Unit B, North Chatham, MA 02650
    409 Orleans Rd Unit B, North Chatham, MA 02650
    /22

    $435,000 Sold Mar 14, 2025

    409 Orleans Rd Unit B, North Chatham, MA 02650

    • 2 Beds
    • 1 Bath
    • 1,013 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Above List Price
    • $429/SF
    • 6 Days On Market

    Current Estimated Value $436,190

    Last Listing Agent Debra Bassett Cape Cod Associates R E

    409 Orleans Rd Unit B, North Chatham, MA 02650
    • 36 Misty Meadow Ln Unit 1, North Chatham, MA 02650
      36 Misty Meadow Ln Unit 1, North Chatham, MA 02650
      36 Misty Meadow Ln Unit 1, North Chatham, MA 02650
      /26

      Est $426,358 Not Listed For Sale

      • 1 Bed
      • 1.5 Baths
      • 836 Sq Ft

      36 Misty Meadow Ln Unit 1, North Chatham, MA 02650

      36 Misty Meadow Ln Unit 1, North Chatham, MA 02650
  • 2550 Main St, South Chatham, MA 02659
    2550 Main St, South Chatham, MA 02659
    /2

    $3,999,900 New Construction

    • 3 Beds
    • 4.5 Baths
    • 4,393 Sq Ft

    2550 Main St, South Chatham, MA 02659

    One of two new Eastward Company homes being constructed in this private enclave in Chatham. It offers the opportunity to select your own finishes and extras at this stage of construction with occupancy for next Summer 2026. The builder is committed to providing the utmost quality and proven floor plans which appeal to the most discerning buyer. Incorporating expansive open living space you will

    Ward Brown William Raveis Real Estate & Home Services

    2550 Main St, South Chatham, MA 02659
  • 108 Misty Meadow Ln Unit A, North Chatham, MA 02650
    108 Misty Meadow Ln Unit A, North Chatham, MA 02650
    108 Misty Meadow Ln Unit A, North Chatham, MA 02650
    /27

    $590,000 Sold Mar 12, 2025

    108 Misty Meadow Ln Unit A, North Chatham, MA 02650

    • 2 Beds
    • 2 Baths
    • 1,489 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Above List Price
    • $396/SF
    • 3 Days On Market

    Current Estimated Value $590,359

    Last Listing Agent Diane Donahue Gibson Sotheby's International Realty

    108 Misty Meadow Ln Unit A, North Chatham, MA 02650
    • 56 Meadowbrook Rd, North Chatham, MA 02650
      56 Meadowbrook Rd, North Chatham, MA 02650
      56 Meadowbrook Rd, North Chatham, MA 02650
      /29

      Est $1,159,826 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,692 Sq Ft

      56 Meadowbrook Rd, North Chatham, MA 02650

      56 Meadowbrook Rd, North Chatham, MA 02650
  • 56 Skyline Dr, Chatham, MA 02633
    56 Skyline Dr, Chatham, MA 02633
    56 Skyline Dr, Chatham, MA 02633
    /32

    $1,599,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,392 Sq Ft

    56 Skyline Dr, Chatham, MA 02633

    Enjoy breezy summer days and lots of lake time from this updated 4 Bedroom home located on Great Hill. With deeded rights to Lovers Lake and lake access less than 100 yards outside your door, this classic cape style home invites family fun & enjoying nature all year long. Updates include granite/stainless kitchen w/ breakfast bar, a great room / rec room w/ vaulted beamed ceiling, french doors,

    Janet Stuart Coldwell Banker Realty - Concord

    56 Skyline Dr, Chatham, MA 02633
  • 56 Chatham Crest Dr, Chatham, MA 02633
    56 Chatham Crest Dr, Chatham, MA 02633
    56 Chatham Crest Dr, Chatham, MA 02633
    /50

    $995,000 Sold Oct 10, 2025

    56 Chatham Crest Dr, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 1,729 Sq Ft
    • Built 1978

    Last Sold Summary

    • 6% Above List Price
    • $575/SF
    • 5 Days On Market

    Last Listing Agent Natalia Weiner Gibson Sotheby's International Realty

    56 Chatham Crest Dr, Chatham, MA 02633
    • 31 Great Hill Rd, Chatham, MA 02633
      31 Great Hill Rd, Chatham, MA 02633
      31 Great Hill Rd, Chatham, MA 02633
      /48

      Est $1,118,128 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,977 Sq Ft

      31 Great Hill Rd, Chatham, MA 02633

      31 Great Hill Rd, Chatham, MA 02633
  • 98 Horizon Dr, Chatham, MA 02633
    98 Horizon Dr, Chatham, MA 02633
    98 Horizon Dr, Chatham, MA 02633
    /39

    $2,195,000 Pending

    • 3 Beds
    • 4.5 Baths
    • 3,310 Sq Ft

    98 Horizon Dr, Chatham, MA 02633

    Ready to move-in! New construction and a great value in Chatham with deeded rights to Lover's Lake for swimming, fishing and boating and room for a future pool. Classic Cape Cod home sited high on Great Hills Estates with over 3000 s.f. with 3 BR's and 4.5 baths. Open floor plan offers great room with soaring vaulted ceilings, fireplace and adjacent cook's kitchen with center breakfast island and

    Lori Fanning Smith Compass Massachusetts, LLC

    98 Horizon Dr, Chatham, MA 02633
  • 15 Stephen Dr, Chatham, MA 02633
    15 Stephen Dr, Chatham, MA 02633
    15 Stephen Dr, Chatham, MA 02633
    /24

    $780,000 Sold Jun 06, 2025

    15 Stephen Dr, Chatham, MA 02633

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1971

    Last Sold Summary

    • 1% Above List Price
    • $682/SF
    • 5 Days On Market

    Current Estimated Value $806,926

    Last Listing Agent Stephen Laska RE/MAX Vision

    15 Stephen Dr, Chatham, MA 02633
    • 79 Nob Hill Rd, Chatham, MA 02633
      79 Nob Hill Rd, Chatham, MA 02633
      79 Nob Hill Rd, Chatham, MA 02633
      /27

      Est $722,253 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft

      79 Nob Hill Rd, Chatham, MA 02633

      79 Nob Hill Rd, Chatham, MA 02633

Showing Results 161 - 200, Page 5 of 18

Massachusetts Barnstable County Chatham

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