9,641

Chatham, MA Homes

Section Image
  • /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 $480,024

    Last Listing Agent Susan Colliton Berkshire Hathaway HomeServices Robert Paul Properties

    912 Main St Unit 304, Chatham, MA 02633
    • /60

      Est $2,847,113

      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

      • 23% Below List Price
      • $1,114/SF
      • 210 Days On Market
      • Last Sold Price $3,675,000
      • Jun 28, 2024

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

  • /52

    $12,950,000

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

    301 Whidah Rd, North Chatham, MA 2650

    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 vistas and invite natural light to pour in throughout the home. Indoor and outdoor spaces flow effortlessly, from sun-drenched rooms to generous

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    301 Whidah Rd, North Chatham, MA 2650
  • /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
    • /53

      Est $2,431,353

      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

      • 30% Above List Price
      • $702/SF
      • 2 Days On Market
      • Last Sold Price $1,875,000
      • Sep 18, 2023

      Last Listing Agent David Doherty Kinlin Grover Compass

  • /33

    $899,000

    • 2 Beds
    • 2 Baths
    • 2,127 Sq Ft

    1068 Main St Unit 1068, Chatham, MA 02633

    Welcome to "the Perch"! This 3 level townhome is located in the coastal town of Chatham! This serene setting overlooks Perch Pond where nature abounds.The complex is located close to downtown shops & restaurants, local beaches & the Old Colony Rail Trail. There is a finished lower level w/ great room and a sleeping area (2 queen beds) as well as 2 bedroom suites incl a first floor option. If you

    Kristin Coletti William Raveis R.E. & Home Services

    1068 Main St Unit 1068, 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
    • /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
      • Jun 21, 2024

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /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
  • /15

    $615,000

    Sold Apr 15, 2026

    39 Meadow Brook Rd, Chatham, MA 02650

    • 2 Beds
    • 1 Bath
    • 769 Sq Ft
    • Built 1957

    Last Sold Summary

    • 9% Below List Price
    • $800/SF
    • 129 Days On Market

    Current Estimated Value $682,393

    Last Listing Agent Karin Baxter-King Christie's International Real Estate Atlantic Brokerage

    39 Meadow Brook Rd, Chatham, MA 02650
    • /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
      • Jul 26, 2024

      Last Listing Agent Kimberly Robbins Compass Massachusetts, LLC

  • /50

    $1,495,000

    • 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
  • /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 $1,096,391

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

    20 Judys Ln, South Chatham, MA 2659
    • /77

      Est $4,655,464

      Not Listed For Sale

      79 Barcliff Ave, Chatham, MA 02633

      • 3 Beds
      • 5 Baths
      • 3,724 Sq Ft
      • Built 2007
      79 Barcliff Ave, Chatham, MA 02633

      Last Sold Summary

      • 3% Above List Price
      • $1,208/SF
      • 3 Days On Market
      • Last Sold Price $4,500,000
      • Apr 23, 2025

      Last Listing Agent Doug Grattan Christie's International Real Estate Atlantic Brokerage

  • /53

    $865,900

    $29K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,688 Sq Ft

    61 Oak Hill Rd, Chatham, MA 02633

    Easy one-floor living in Chatham can be yours in this sun-filled 2 bedroom home that includes deeded rights to Stillwater Pond. The floor plan offers a good-sized living room w/bay window and gas fireplace, a cozy eat-in-kitchen with laundry area & pantry, and a bright family room that features newer sliders to a deck overlooking the level back yard. Down the hall you'll find the primary bedroom

    Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

    61 Oak Hill Rd, 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 $1,457,472

    Last Listing Agent Jan Pulit Kinlin Grover Compass

    30 Monomessat Way, Chatham, MA 02633
    • /35

      Est $3,851,478

      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

      • 10% Below List Price
      • $1,217/SF
      • 64 Days On Market
      • Last Sold Price $4,300,000
      • Nov 22, 2024

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /36

    $699,000

    • 2 Beds
    • 2 Baths
    • 996 Sq Ft

    216 Orleans Rd Unit E, North Chatham, MA 02650

    Beautifully appointed 2 bedroom/2 bath second floor unit condominium in North Chatham in quiet association. Close to 3 harbor beaches and downtown Chatham, this location can't be beat. Pleasant sunny exposure with sizable outside deck. Extensive recent renovations include: new electrical & plumbing, air conditioning, overhead lighting, kitchen wth high end appliances, bathrooms with heated

    Ella Leavitt Compass

    216 Orleans Rd Unit E, North 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 $369,302

    Last Listing Agent Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

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

      Est $2,325,549

      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

      • 1% Below List Price
      • $904/SF
      • 78 Days On Market
      • Last Sold Price $2,350,000
      • Jan 24, 2025

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /30

    $1,695,000

    Pending
    • 2 Beds
    • 3.5 Baths
    • 2,016 Sq Ft

    68 Levis Path, South Chatham, MA 2659

    Welcome to Chatham! Be in for summer and enjoy this move-in ready, meticulously maintained home offering comfort and easy location to beach and restaurants. The open floor plan is perfect for entertaining, with bright living spaces that flow seamlessly throughout. The chef's kitchen showcases high-end finishes, premium appliances, custom cabinetry, and a spacious island ideal for gathering.This

    Betsy Hargreaves Gibson Sotheby's International Realty

    68 Levis Path, South Chatham, MA 2659
  • /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 $1,870,095

      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

      • 13% Above List Price
      • $870/SF
      • 14 Days On Market
      • Last Sold Price $1,650,000
      • Sep 04, 2024

      Last Listing Agent Mary Lyttle Beach Road Properties

  • /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
  • /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 $3,418,990

    Last Listing Agent Ricardo Rodriguez Coldwell Banker Realty - Boston

    450 Main St, Chatham, MA 02633
    • /59

      Est $3,088,504

      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

      • 11% Above List Price
      • $1,325/SF
      • 82 Days On Market
      • Last Sold Price $2,777,500
      • Jun 15, 2023

      Last Listing Agent Tim Bailey John C Ricotta & Assoc.

  • /47

    $1,650,000

    • 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
  • /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 $7,590,987

    Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    552 Shore Rd, Chatham, MA 02633
    • /35

      Est $1,197,945

      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

      • 26% Above List Price
      • $1,275/SF
      • 10 Days On Market
      • Last Sold Price $954,000
      • Sep 13, 2024

      Last Listing Agent Lori Jurkowski Compass

  • /36

    $699,900

    Pending
    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    35 Bobbie's Ln, Chatham, MA 02659

    35 Bobbies Lane, South Chatham--an exceptional value in an area of significantly higher-priced homes. This small 3+ bedroom offers a rare opportunity to own just about a half mile from Forest Beach, with public tennis courts right across the street for an active Cape Cod lifestyle.The home offers solid potential but will benefit from updating, including the heating system and replacement of the

    Richard Waystack Keller Williams Realty

    35 Bobbie's Ln, 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 $680,969

      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

      • 7% Above List Price
      • $690/SF
      • 38 Days On Market
      • Last Sold Price $638,000
      • Nov 18, 2024

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

  • /35

    $1,650,000

    • 3 Beds
    • 2 Baths
    • 2,169 Sq Ft

    48 Glover Square, Chatham, MA 02633

    Chatham By The Sea. Rare 50-year offering at 48 Glover Square presents a premier opportunity in Chatham. Incredible, coveted location 2 blocks to downtown Chatham Village. Chatham Fish Pier, Oyster Pond, Veterans Field, shopping, grocery, tennis, golf 1/2 mile away. Spacious one-floor living with room to reimagine! Ranch home is 1531 square feet and includes 3 bedrooms, large formal living room

    Laurie McCann Gibson Sotheby's International Realty

    48 Glover Square, Chatham, MA 02633
  • /2

    $540,000

    Sold Sep 18, 2025

    0 Reynolds Cir Unit 22501745, Chatham, MA 02633

    • Land
    • 1.2 Acres
    • $450,000 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 81 Days On Market

    Last Listing Agent Derek Greene The Greene Realty Group

    0 Reynolds Cir Unit 22501745, Chatham, MA 02633
    • /55

      Est $2,689,928

      Not Listed For Sale

      15 Edgewater Dr, Chatham, MA 02633

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 1960
      15 Edgewater Dr, Chatham, MA 02633

      Last Sold Summary

      • 3% Above List Price
      • $1,243/SF
      • 119 Days On Market
      • Last Sold Price $2,610,000
      • Feb 28, 2025

      Last Listing Agent Shane Masaschi 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
  • /53

    $1,495,000

    Sold Dec 15, 2025

    291 Ridgevale Rd, Chatham, MA 02633

    • 3 Beds
    • 1.5 Baths
    • 1,424 Sq Ft
    • Built 1950

    Last Sold Summary

    • $1,050/SF
    • 8 Days On Market

    Current Estimated Value $1,507,424

    Last Listing Agent Jan Nowak Craigville Realty Co

    291 Ridgevale Rd, Chatham, MA 02633
    • /54

      Est $3,742,519

      Not Listed For Sale

      173 Kendrick Rd, North Chatham, MA 02650

      • 6 Beds
      • 4.5 Baths
      • 4,106 Sq Ft
      • Built 2000
      173 Kendrick Rd, North Chatham, MA 02650

      Last Sold Summary

      • 1% Above List Price
      • $900/SF
      • 174 Days On Market
      • Last Sold Price $3,695,000
      • Mar 03, 2025

      Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

  • /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
  • /20

    $1,975,000

    Sold Oct 08, 2025

    20 Hardings Beach Rd, Chatham, MA 02633

    • 4 Beds
    • 3.5 Baths
    • 2,770 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Below List Price
    • $713/SF
    • 31 Days On Market

    Current Estimated Value $1,807,933

    Last Listing Agent Chris Rhinesmith Compass Massachusetts, LLC

    20 Hardings Beach Rd, Chatham, MA 02633

Showing Results 81 - 120, Page 3 of 18

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