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Chatham, MA Homes for Sale | Realty.com
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82 listings
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3 beds

Homes for Sale in Chatham, MA

Homes for Sale in Chatham, MA

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17 of 82 Listings
Map

Homes for Sale in Chatham, MA

17 of 82 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas
  1. 764 Riverview Dr — photoNewOpen house Sat, Oct 10 · 10:30 AM24Active

    $1,650,000

    3 bd · 3 ba · 1,902 sqft

    764 Riverview Dr, Chatham, MA

    Dawn Marie Boynton · Berkshire Hathaway HomeServices Robert Paul Properties

  2. 35 Crows Pond Road — photo6Active

    $3,995,000

    3 bd · 5 ba · 4,400 sqft

    35 Crows Pond Road, Chatham, MA

    Betsy Hargreaves · Gibson Sotheby's International Realty

  3. 800 Riverview Drive — photo40Active

    $975,000

    3 bd · 2 ba · 1,820 sqft

    800 Riverview Drive, Chatham, MA

    Shane K Masaschi · Compass

  4. 2118 Main St — photo33Active

    $1,399,000

    4 bd · 3 ba · 2,670 sqft

    2118 Main St, Chatham, MA

    Marcie Smith · Gibson Sotheby's International Realty

  5. 2653 Main St — photo15Active

    $950,000

    3 bd · 3 ba · 2,252 sqft

    2653 Main St, Chatham, MA

    Kevin A. Pepe · Commercial Realty Advisors, Inc.

  6. 9 Bassing Harbor — photo42Active

    $3,299,900

    3 bd · 4 ba · 3,157 sqft

    9 Bassing Harbor, Chatham, MA

    Andrew Grattan · Christie's International Real Estate Atlantic Brokerage

  7. Active

    $3,299,900

    3 bd · 4 ba · 3,157 sqft

    9 Bassing Harbor Road, Chatham, MA

    The Grattan Group · Christie's International Real Estate Atlantic Brokerage

  8. 20 Stoughton Lane — photo32Active

    $2,285,000

    5 bd · 4 ba · 2,478 sqft

    20 Stoughton Lane, Chatham, MA

    Elaine Babineau Lomenzo · William Raveis Real Estate & Home Services

  9. 2673 Main St — photo42Active

    $849,000

    4 bd · 2 ba · 1,635 sqft

    2673 Main St, Chatham, MA

    Barbara Garside · eXp Realty LLC

  10. 26 Chatham Heights Road — photo62Active

    $3,100,000

    3 bd · 4 ba · 4,053 sqft

    26 Chatham Heights Road, Chatham, MA

    Chris Rhinesmith · Compass Massachusetts, LLC

  11. 12 Pond Street — photo91Active

    $6,875,000

    4 bd · 5 ba · 4,512 sqft

    12 Pond Street, Chatham, MA

    Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties

  12. 169 Tisquantum Road — photo78Active

    $4,495,000

    5 bd · 5 ba · 5,887 sqft

    169 Tisquantum Road, Chatham, MA

    Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties

  13. 32 Tip Cart Dr — photo27Active

    $1,295,000

    3 bd · 2 ba · 1,802 sqft

    32 Tip Cart Dr, Chatham, MA

    Shane Masaschi · Compass

  14. 288 Training Field Road — photoOpen house Sat, Oct 10 · 10:00 AM31Active

    $1,200,000

    2 bd · 3 ba · 2,380 sqft

    288 Training Field Road, Chatham, MA

    Karen Quinn · William Raveis Real Estate & Home Services

  15. 20 Lords Pond Road — photo48Active

    $2,199,900

    3 bd · 3 ba · 2,576 sqft

    20 Lords Pond Road, Chatham, MA

    The Grattan Group · Christie's International Real Estate Atlantic Brokerage

  16. 20 Lords Pond Lane — photo42Active

    $2,199,900

    3 bd · 4 ba · 2,576 sqft

    20 Lords Pond Lane, Chatham, MA

    Andrew Grattan · Christie's International Real Estate Atlantic Brokerage

  17. 39 Jedidiah Way — photo38Active

    $1,495,000

    2 bd · 2 ba · 1,810 sqft

    39 Jedidiah Way, Chatham, MA

12…4

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Listing data & MLS disclosures

Cape Cod & Islands Association of REALTORS
The data relating to real estate for sale on this site comes from the Broker Reciprocity of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than the brokerage firm owning this website are marked with the IDX Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor the brokerage firm owning this website shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All Rights Reserved.
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The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-10-06 10:18:00 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #1000018

    Call Thomas

    Nearby areas

    ZIP codes

    • 02631 (81)
    • 02601 (79)
    • 02633 (69)
    • 02675 (64)
    • 02642 (62)
    • 02655 (60)
    • 02653 (59)
    • 02664 (58)

    Cities

    • Barnstable (129)
    • Yarmouth (83)
    • Brewster (81)
    • Dennis (79)
    • Harwich (64)
    • Eastham (62)
    • Orleans (59)
    • Wellfleet (53)

    Chatham, MA community profile

    Area
    16.7 sq. mi.

    Source: HJN community data

    Chatham housing market

    September 2026 · This period is still settling

    Selling at 97.2% of asking price

    Buyers here are paying below asking. MLS · 22 sales · as of Sep 28, 2026

    Homes on the market · MLS, as of Sep 27, 2026–Sep 28, 2026

    Median list price
    $3,100,000
    Homes for sale
    38
    Median days on market
    22 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 9, 2026

    Median home size
    1,902 sq. ft.