9,636

Chatham, MA Homes

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    • /30

      Est $1,239,215 Not Listed For Sale

      6 Palmer Dr, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 1,702 Sq Ft
      • Built 1974
      6 Palmer Dr, Chatham, MA 02633

      Last Sold Summary

      • 24% Above List Price
      • $588/SF
      • 41 Days On Market

      Last Sold Price $1,000,000

      Last Listing Agent Shane Masaschi Compass

  • /42

    $12,950,000

    • 5 Beds
    • 6.5 Baths
    • 7,259 Sq Ft

    301 Whidah Rd, Chatham, MA 02650

    Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha’s Vineyard Interior Designs. Walls of glass frame sweeping views and fill the home with natural light, while indoor and outdoor spaces flow seamlessly to expansive decks, terraces, and a resort-style pool

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    301 Whidah Rd, Chatham, MA 02650
  • /32

    $10,000,000 Sold Sep 24, 2025

    108 Shore Rd, Chatham, MA 02633

    • 7 Beds
    • 9 Baths
    • 6,276 Sq Ft
    • Built 1920

    Last Sold Summary

    • 16% Below List Price
    • $1,593/SF
    • 67 Days On Market

    Last Listing Agent Frank Denauw Frank G. Denauw, Esq.

    108 Shore Rd, Chatham, MA 02633
    • /5

      Est $1,917,045 Not Listed For Sale

      172 Barcliff Ave, Chatham, MA 02633

      • 5 Beds
      • 3 Baths
      • 1,724 Sq Ft
      • Built 1900
      172 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 1% Above List Price
      • $1,102/SF
      • 2 Days On Market

      Last Sold Price $1,900,000

      Last Listing Agent Louise Coakley Better Homes and Gardens Real Estate - The Shanahan Group

  • /49

    $1,495,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft

    137 Shane Dr, Chatham, MA 02633

    Perfectly positioned on a corner lot in a quiet neighborhood, this beautifully maintained home offers peaceful living just moments from everything Chatham has to offer. Located less than a mile from downtown, it provides easy access to shops, restaurants, beaches, and landmarks including the Fish Pier, Veterans Field, Seaside Links, and Chatham Bars Inn. Offering two levels with 2,448 sqft (1,530

    Tom Riley Compass Massachusetts, LLC

    137 Shane Dr, Chatham, MA 02633
  • /31

    $1,700,000 Sold Nov 17, 2025

    44 Emery Ln, North Chatham, MA 02650

    • 3 Beds
    • 2 Baths
    • 1,743 Sq Ft
    • Built 1983

    Last Sold Summary

    • $975/SF
    • 34 Days On Market

    Current Estimated Value $1,732,163

    Last Listing Agent Kathleen Phelan Compass

    44 Emery Ln, North Chatham, MA 02650
    • /60

      Est $3,023,739 Not Listed For Sale

      184 Barcliff Ave, Chatham, MA 02633

      • 4 Beds
      • 5 Baths
      • 3,298 Sq Ft
      • Built 2024
      184 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 18% Below List Price
      • $1,114/SF
      • 210 Days On Market

      Last Sold Price $3,675,000

      Last Listing Agent The Bohman Hartung Group Gibson Sotheby's International Realty

  • /37

    $7,999,000

    • 4 Beds
    • 6 Baths
    • 4,735 Sq Ft

    246 Stage Island Rd, Chatham, MA 02633

    Set on nearly an acre with commanding views of Stage Harbor, this Stage Island residence combines timeless elegance with modern comfort. The foyer opens to a dramatic living room framed by expansive windows and a stylish kitchen with an island and dining area that extends to a generous deck—perfect for entertaining. The main level also offers a private ensuite bedroom, den, and laundry. Upstairs

    Chris Rhinesmith Compass

    246 Stage Island Rd, Chatham, MA 02633
  • /10

    $510,000 Sold Jan 20, 2026

    22 Pine Knoll Ave, Chatham, MA 02633

    • 3 Beds
    • 0.5 Baths
    • 532 Sq Ft
    • Built 1947

    Last Sold Summary

    • 7% Below List Price
    • $959/SF
    • 0 Days On Market

    Current Estimated Value $530,242

    Last Listing Agent Brian Mullen Options 153, LLC

    22 Pine Knoll Ave, Chatham, MA 02633
    • /53

      Est $2,319,121 Not Listed For Sale

      390 Old Harbor Rd, Chatham, MA 02633

      • 4 Beds
      • 2.5 Baths
      • 2,670 Sq Ft
      • Built 1988
      390 Old Harbor Rd, Chatham, MA 02633

      Last Sold Summary

      • 24% Above List Price
      • $702/SF
      • 2 Days On Market

      Last Sold Price $1,875,000

      Last Listing Agent David Doherty Kinlin Grover Compass

  • /40

    $1,195,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,026 Sq Ft

    3 Oyster Dr, Chatham, MA 02633

    Welcome home to 3 Oyster Drive, a perfectly idyllic Chatham getaway! This enchanting cottage enjoys dazzling water views and a prime location near Outermost Harbor Marina, beaches, & Town. This 3 BR, 2 BA home is a blend of classic Cape Cod and some newer features and is the ideal backdrop to begin your own Chatham story. Many will find the home comfortable just the way it is, or choose to take

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    3 Oyster Dr, Chatham, MA 02633
  • /28

    $461,260 Sold Nov 10, 2025

    912 Main St Unit 304, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,231 Sq Ft
    • Built 1999

    Last Sold Summary

    • 1% Below List Price
    • $375/SF
    • 4 Days On Market

    Current Estimated Value $461,331

    Last Listing Agent Susan Colliton Berkshire Hathaway HomeServices Robert Paul Properties

    912 Main St Unit 304, Chatham, MA 02633
    • /74

      Est $5,279,323 Not Listed For Sale

      581 Shore Rd, Chatham, MA 02633

      • 5 Beds
      • 6.5 Baths
      • 4,452 Sq Ft
      • Built 2018
      581 Shore Rd, Chatham, MA 02633

      Last Sold Summary

      • 6% Above List Price
      • $1,123/SF
      • 49 Days On Market

      Last Sold Price $5,000,000

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /17

    $6,950,000 Pending

    • 7 Beds
    • 2.5 Baths
    • 2,552 Sq Ft

    150 Main St, Chatham, MA 02633

    Presenting a rare and extraordinary opportunity to create the ultimate in-town beach house in the heart of Chatham Village. Ideally set on 1.52 acres in one of Cape Cod's most sought-after neighborhoods, the seven-bedroom residence features a rolling lawn that gives way to a pristine, private sandy beach on Chatham Harbor, with views of North Beach and the Atlantic Ocean beyond. Showcasing

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    150 Main St, Chatham, MA 02633
  • /12

    $750,000 Sold May 30, 2025

    86 Vineyard Ave, Chatham, MA 02633

    • 3 Beds
    • 2 Baths
    • 2,625 Sq Ft
    • Built 1947

    Last Sold Summary

    • 12% Below List Price
    • $286/SF
    • 24 Days On Market

    Current Estimated Value $877,590

    Last Listing Agent Phyllis Power Compass

    86 Vineyard Ave, Chatham, MA 02633
    • /10

      Est $924,395 Not Listed For Sale

      30 Oceanview Terrace, Chatham, MA 02633

      • 2 Beds
      • 1 Bath
      • 648 Sq Ft
      • Built 1953
      30 Oceanview Terrace, Chatham, MA 02633

      Last Sold Summary

      • 42% Above List Price
      • $1,006/SF
      • 4 Days On Market

      Last Sold Price $652,000

      Last Listing Agent Daren Marvin Sotheby's International Realty

  • /39

    $1,469,000

    • 5 Beds
    • 10 Baths
    • 11,000 Sq Ft

    558 Fox Hill Rd, Chatham, MA 02633

    Co-ownership opportunity. Fox Hill, a spectacular waterfront retreat sited proudly on nearly 3 acres in a coveted North Chatham location! Within steps to a private beach and dock, this custom shingle residence was designed to accommodate large summer gatherings or cozy weekend getaways! Stunning views of Crows Pond, Eastward Ho and Pleasant Bay can be enjoyed throughout the property, while a

    Brian Dougherty Corcoran Property Advisors

    558 Fox Hill Rd, Chatham, MA 02633
  • /44

    $952,500 Sold Mar 24, 2026

    24 Chickadee Ln, Chatham, MA 02633

    • 2 Beds
    • 2 Baths
    • 1,504 Sq Ft
    • Built 1980

    Last Sold Summary

    • 13% Below List Price
    • $633/SF
    • 119 Days On Market

    Last Listing Agent Amy Harbeck Kinlin Grover Compass

    24 Chickadee Ln, Chatham, MA 02633
    • /64

      Not Listed For Sale

      111 Barcliff Ave, Chatham, MA 02633

      • 8 Beds
      • 4.5 Baths
      • 4,413 Sq Ft
      • Built 1910
      111 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • $736/SF
      • 250 Days On Market

      Last Sold Price $3,250,000

      Last Listing Agent Kimberly Robbins Compass Massachusetts, LLC

  • /50

    $1,650,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,810 Sq Ft

    39 Jedidiah Way, Chatham, MA 02633

    39 Jedidiah Way, has been gently utilized by the same family for the past 29 years, serving as a reliable summer retreat. Situated on a .5-acre elevated lot overlooking a wooded cul-de-sac, this property boasts direct access to the Old Colony Rail Trail, a unique feature among current Chatham offerings. Enjoy the convenience of being just 1 mile from Nantucket Sound Beaches or capitalize on the

    Tom Jones Berkshire Hathaway HomeServices Robert Paul Properties

    39 Jedidiah Way, Chatham, MA 02633
  • /47

    $1,095,000 Sold Jul 18, 2025

    20 Judys Ln, South Chatham, MA 2659

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

    Last Sold Summary

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

    Current Estimated Value $1,047,739

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

    20 Judys Ln, South Chatham, MA 2659
    • /35

      Est $4,255,597 Not Listed For Sale

      39 Seaview Terrace, Chatham, MA 02633

      • 4 Beds
      • 6.5 Baths
      • 3,533 Sq Ft
      • Built 2007
      39 Seaview Terrace, Chatham, MA 02633

      Last Sold Summary

      • 1% Below List Price
      • $1,217/SF
      • 64 Days On Market

      Last Sold Price $4,300,000

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /63

    $1,495,000

    • 3 Beds
    • 2.5 Baths
    • 2,441 Sq Ft

    28 Lakeview Ave, Chatham, MA 02633

    Welcome to 28 Lakeview Ave...a Riverbay gem in a natural setting. Beautifully renovated with hardwood throughout, this 3 bedroom, 2.5 bath home offers a comfortable floor plan including a first floor primary ensuite bedroom and 2 large guest bedooms and bath on the second level. In addition to the inviting living room and dining room, adjacent to well apppointed eat-in kitchen, the den with

    Ella Leavitt Compass

    28 Lakeview Ave, Chatham, MA 02633
  • /3

    $1,370,000 Sold Jul 17, 2025

    30 Monomessat Way, Chatham, MA 02633

    • 3 Beds
    • 2.5 Baths
    • 2,877 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Below List Price
    • $476/SF
    • 18 Days On Market

    Current Estimated Value $1,405,145

    Last Listing Agent Jan Pulit Kinlin Grover Compass

    30 Monomessat Way, Chatham, MA 02633
    • /11

      Est $5,063,209 Not Listed For Sale

      84 Doane Rd, Chatham, MA 02633

      • 5 Beds
      • 9 Baths
      • 5,750 Sq Ft
      • Built 2022
      84 Doane Rd, Chatham, MA 02633

      Last Sold Summary

      • 1% Above List Price
      • $870/SF
      • 176 Days On Market

      Last Sold Price $5,000,000

      Last Listing Agent Sandra Tanco Kinlin Grover Compass

  • /9

    $5,750,000

    • 3 Beds
    • 6 Baths
    • 4,902 Sq Ft

    7 Cove Rd, Chatham, MA 02650

    Tucked within a coveted North Chatham setting of Harbor Coves and offering access to a private association beach, this exceptional Gambrel-style residence currently under construction with Harbor Builders presents a sophisticated coastal retreat.The property offers generous indoor and outdoor living spaces on a half an acre. The main level features an inviting open floor plan where a

    Chris Rhinesmith Compass Massachusetts, LLC

    7 Cove Rd, Chatham, MA 02650
  • /27

    $349,999 Sold Feb 02, 2026

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft
    • Built 1963

    Last Sold Summary

    • 12% Below List Price
    • $503/SF
    • 76 Days On Market

    Current Estimated Value $361,080

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    109 Misty Meadow Ln Unit 2, North Chatham, MA 02650
    • /31

      Est $2,498,656 Not Listed For Sale

      22 Cahoons Hollow Rd, Chatham, MA 02633

      • 3 Beds
      • 3.5 Baths
      • 2,600 Sq Ft
      • Built 2009
      22 Cahoons Hollow Rd, Chatham, MA 02633

      Last Sold Summary

      • 6% Above List Price
      • $904/SF
      • 78 Days On Market

      Last Sold Price $2,350,000

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /35

    $919,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,713 Sq Ft

    46 Chippingstone Rd, Chatham, MA 02633

    Riverbay, Chatham... True One Level living with Garage/parking on home level. 8 room custom built ranch with side loading garages, high profile roofline, integrated front porch. Inside, abundant common areas and living space. entrance hallway opens to the living and dining rooms, and two hallways leading to the 3 bedrooms. At the back of the home- 3 additional rooms: a fireplaced family room, an

    Derek Greene The Greene Realty Group

    46 Chippingstone Rd, Chatham, MA 02633
  • /32

    $5,750,000 Sold Sep 30, 2025

    25 Wikis Way, Chatham, MA 02633

    • 4 Beds
    • 4.5 Baths
    • 4,654 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Below List Price
    • $1,235/SF
    • 107 Days On Market

    Current Estimated Value $6,005,630

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    25 Wikis Way, Chatham, MA 02633
    • /37

      Est $1,933,675 Not Listed For Sale

      31 Mill Pond Rd, Chatham, MA 02633

      • 4 Beds
      • 2.5 Baths
      • 1,896 Sq Ft
      • Built 1950
      31 Mill Pond Rd, Chatham, MA 02633

      Last Sold Summary

      • 17% Above List Price
      • $870/SF
      • 14 Days On Market

      Last Sold Price $1,650,000

      Last Listing Agent Mary Lyttle Beach Road Properties

  • /37

    $1,200,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    27 Martha Kendrick Dr, Chatham, MA 02633

    Welcome to this delightful 3-bedroom, 2.5-bath Cape-style home nestled just moments from the heart of downtown Chatham. With its classic architecture and thoughtful layout, this property offers the perfect blend of coastal charm and modern convenience.Step inside to discover sun-drenched living spaces with abundant natural light and a cozy fireplace that anchors the main living area. The

    Kathy Doyle Gibson Sotheby's International Realty

    27 Martha Kendrick Dr, Chatham, MA 02633
  • /29

    $3,400,000 Sold Dec 30, 2025

    450 Main St, Chatham, MA 02633

    • 5 Beds
    • 5.5 Baths
    • 7,396 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Below List Price
    • $460/SF
    • 55 Days On Market

    Current Estimated Value $3,410,545

    Last Listing Agent Ricardo Rodriguez Coldwell Banker Realty - Boston

    450 Main St, Chatham, MA 02633
    • /59

      Est $3,139,897 Not Listed For Sale

      81 Mill Pond Rd, Chatham, MA 02633

      • 4 Beds
      • 3 Baths
      • 2,097 Sq Ft
      • Built 1924
      81 Mill Pond Rd, Chatham, MA 02633

      Last Sold Summary

      • 13% Above List Price
      • $1,325/SF
      • 82 Days On Market

      Last Sold Price $2,777,500

      Last Listing Agent Tim Bailey John C Ricotta & Assoc.

  • /66

    $3,299,900 Pending

    • 3 Beds
    • 3.5 Baths
    • 2,940 Sq Ft

    20 Jessies Landing, Chatham, MA 2633

    Welcome to this beautifully crafted residence in Jessie's Landing, an exclusive Eastward Companies development, ideally located just a short walk to Harding's Beach. Set on nearly a half-acre and outside the flood zone, this thoughtfully designed home offers the perfect blend of Cape Cod charm, modern comfort, and peace of mind. The open floor plan is ideal for everyday living and entertaining,

    Doug Grattan Christie's International Real Estate Atlantic Brokerage

    20 Jessies Landing, Chatham, MA 2633
  • /42

    $11,250,000 Sold Jun 09, 2025

    552 Shore Rd, Chatham, MA 02633

    • 7 Beds
    • 6.5 Baths
    • 5,868 Sq Ft
    • Built 1930

    Last Sold Summary

    • 19% Below List Price
    • $1,917/SF
    • 326 Days On Market

    Current Estimated Value $7,546,084

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    552 Shore Rd, Chatham, MA 02633
    • /35

      Est $1,182,111 Not Listed For Sale

      8 Oyster Dr, Chatham, MA 02633

      • 3 Beds
      • 1 Bath
      • 748 Sq Ft
      • Built 1947
      8 Oyster Dr, Chatham, MA 02633

      Last Sold Summary

      • 24% Above List Price
      • $1,275/SF
      • 10 Days On Market

      Last Sold Price $954,000

      Last Listing Agent Lori Jurkowski Compass

  • /39

    $799,000 Pending

    • 2 Beds
    • 1 Bath
    • 817 Sq Ft

    37 Glendon Way, South Chatham, MA 02659

    Welcome to Chatham MA. Hydrangea House is an adorable Chatham cottage filled with character with 2 beach choices within a short walk, Pleasant St Beach and Forrest Beach. Enjoy Hydrangea House spring, summer, fall & winter alike. .21 acres, privately sited on a lovely street, this 2 bedroom/1 bath home has an open floor plan which includes a light & bright white kitchen with seating at the

    Dee Kerner Compass

    37 Glendon Way, South Chatham, MA 02659
  • /54

    $3,300,000 Sold Jul 22, 2025

    35 Whistler Ln, Chatham, MA 02633

    • 3 Beds
    • 3.5 Baths
    • 2,314 Sq Ft
    • Built 2002

    Last Sold Summary

    • 6% Below List Price
    • $1,426/SF
    • 50 Days On Market

    Last Listing Agent MaryEllen Monahan Today Real Estate

    35 Whistler Ln, Chatham, MA 02633
    • /22

      Est $661,670 Not Listed For Sale

      16 Starfish Ln, Chatham, MA 02633

      • 2 Beds
      • 2 Baths
      • 925 Sq Ft
      • Built 1982
      16 Starfish Ln, Chatham, MA 02633

      Last Sold Summary

      • 4% Above List Price
      • $690/SF
      • 38 Days On Market

      Last Sold Price $638,000

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

Showing Results 81 - 120, Page 3 of 18

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